724:(cAMP), an intracellular signal that serves broadly to inhibit platelet activation. These studies were largely overlooked; in 1998 and 2007 publications, for example, 12-HHT was regarded as either inactive or without significant biological activity. Nonetheless, this early work suggested that 12-HHT may serve as a contributor to monocyte- and neutrophil-based inflammatory responses and 12-oxo-HT may serve as a counterpoise to platelet aggregation responses elicited or promoted by TXA2. Relevant to the latter activity, a later study showed that this inhibitory effect was due to the ability of 12-oxo-HT to act as a partial antagonist of the
238:
161:
38:
829:)-HETE, and 20-hydroxy-LTB4 are ~100, 10, 10, 3, 3, and 1, respectively. All of these binding affinities are considered to be low and therefore indicating that some unknown ligand(s) might bind BLT2 with high affinity. In 2009, 12-HHT was found to bind to the BLT2 receptor with ~10-fold higher affinity than LTB4; 12-HHT did not bind to the BLT1 receptor. Thus, the BLT1 receptor exhibits exquisite specificity, binding 5(
728:: it blocks TXA2 binding to its receptor and thereby the responses of platelets and possibly other tissues to TXA2 as well as agents that depend on stimulating TXA2 production for their activity. Thus, 12-HHT forms simultaneously with, and by stimulating PGI2 production, inhibits TXA2-mediated platelet activation responses while 12-oxo-HT blocks TXA2 receptor binding to reduce not only TXA2-induced
1026:. These results indicate that the 12-HHT/BLT2 receptor axis is a critical contributor to wound healing in mice and possibly humans. The axis operates by recruiting the movement of keratinocytes to close the wound. This mechanism may underlie the suppression of wound healing that accompanies the high dose intake of aspirin and, based on mouse studies, other
541:. Its abundant production during blood clotting, the presence of cyclooxygenases and to a lesser extent thromboxane synthase in a wide range of cell types and tissue, and its production by other pathways imply that 12-HHT has one or more important bioactivities relevant to clotting and, perhaps, other responses.
736:
but possibly also vasospasm and other actions of TXA2. In this view, thromboxane synthase leads to the production of a broadly active arachidonic acid metabolite, TXA2, plus two other arachidonic acid metabolites, 12-HHT and 12-oxo-HT, that serve indirectly to stimulate PGI2 production or directly as
536:
by recruiting nearby platelets into the response as well as exerting effects on other nearby tissues such as contracting blood vessels. These effects combine to trigger blood clotting and limiting blood loss. 12-HHT is a particularly abundant product of these pro-clotting responses, accounting for
949:
pathways in a BLT2 receptor-dependent reaction. Topical treatment of mouse skin with a BLT2 receptor antagonist, LY255283, protects against UVB radiation-induced apoptosis and BLT2-overexpressing transgenic mice exhibited significantly more extensive skin apoptosis in response to UVB irradiation.
912:
which are mediated by these cell types. Drugs that inhibit LTB4 production or binding to BLT1 are in use or development for the latter diseases. In contrast, the production of 12-HHT and expression of BLT2 receptors by human tissues is far wider and more robust than that of the LTB4/BLT2 receptor
991:
from patients with asthma compared to healthy control subjects. Unlike LTB4 and its BLT1 receptor, which are implicated in contributing to allergen-based airway disease in mice and humans, 12-HHT and its BLT2 receptor appear to suppress this disease in mice and may do so in humans. While further
1741:
Hofmann, U; Seefried, S; Meese, C. O.; Mettang, T; HΓΌbel, E; Kuhlmann, U (1990). "Measurement of 12(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid and its metabolite 12-oxo-5Z,8E,10E-heptadecatrienoic acid in human plasma by gas chromatography/negative ion chemical ionization mass spectrometry".
967:, but not 12 other lipoxygenase or cycloxygenase metabolites, showed a statistically significantly increase in bronchoalveolar lavage fluid levels after intratracheal ovalbumin challenge; after this challenge, only 12-HHT, among the monitored BLT2 receptor-activating ligands (LTB4, the 12(
958:
associated with cutaneous inflammation, in response to UVB radiation. These results suggest that the 12-HHT/BLT2 axis can act to suppress inflammation by promoting the orderly death of damaged cells and blocking IL-6 production. Opposition between the pro-inflammatory LTB4/BLT1 and
1017:
deficiency. 12-HHT accumulated in the wounds of the former mouse model. Companion studies using an in vitro scratch test assay indicated that 12-HHT stimulated human and mouse keratinocyte migration by a BLT2 receptor-dependent mechanism that involved the production of
597:); associated with these changes, the differentiated macrophage metabolized arachidonic acid to 12-HHT by a CYP2S1-dependent mechanism. Future studies, therefore may show that cytochromes are responsible for 12-HHT and MDA production in vivo.
992:
studies to probe the role of the 12-HHT/BLT2 axis in human inflammatory and allergic diseases, the current studies indicate that 12-HHT, acting through BLT2, may serve to promote or limit, inflammatory and to promote allergic responses.
1462:
FrΓΆmel, T; Kohlstedt, K; Popp, R; Yin, X; Awwad, K; Barbosa-Sicard, E; Thomas, A. C.; Lieberz, R; Mayr, M; Fleming, I (2013). "Cytochrome P4502S1: A novel monocyte/macrophage fatty acid epoxygenase in human atherosclerotic plaques".
784:
metabolites of arachidonic acid, it binds only LTB4, 20-hydroxy-LTB4, and 12-epi-LTB4; among this same series, BLT2 receptor has far less specificity in that it binds not only LTB4, 20-hydroxy-LTB4, and 12-epi-LTB4 but also
1292:
Sadowitz, P. D.; Setty, B. N.; Stuart, M (1987). "The platelet cyclooxygenase metabolite 12-L-hydroxy-5, 8, 10-hepta-decatrienoic acid (HHT) may modulate primary hemostasis by stimulating prostacyclin production".
1004:
treatment (aspirin, at these doses, inhibits cyclooxygenases-1 and -2 to block their production of 12-HHT), thromboxane synthase knockout, and BLT2 receptor knockout but not TXA2 receptor knockout impair
628:-heptadecatrienoic acid. This non-enzymatic pathway may explain findings that cells can make 12-HHT in excess of TXA2 and also in the absence of active cycloxygenase and/or thromboxane synthase enzymes.
1664:
Agins, A. P.; Thomas, M. J.; Edmonds, C. G.; McCloskey, J. A. (1987). "Identification of 12-keto-5,8,10-heptadecatrienoic acid as an arachidonic acid metabolite produced by human HL-60 leukemia cells".
1030:(NSAID) in humans. Synthetic BLT2 agonists may be useful for speeding the healing of chronic ulcerative wounds, particularly in patients with, for example diabetics, that have impaired wound healing.
1009:-based re-epithelialization and thereby closure of experimentally induced wounds in mice while a synthetic BLT2 receptor agonist accelerates wound closure not only in this mouse model but also in the
696:
Fourteen years after the first publication on its detection in 1973, 12-HHT was reported to stimulate fetal bovine aortic and human umbilical vein endothelial cells to metabolize arachidonic acid to
930:
made to express these receptors by transfection. These findings suggest that the 12-HHT/BLT2 receptor pathway may support the pro-inflammatory (i.e. chemotactic) actions of the LTB4/BLT1 pathway.
1629:
Bergholte, J. M.; Soberman, R. J.; Hayes, R; Murphy, R. C.; Okita, R. T. (1987). "Oxidation of 15-hydroxyeicosatetraenoic acid and other hydroxy fatty acids by lung prostaglandin dehydrogenase".
959:
anti-inflammatory actions of the 12-HHT/BLT2 axes occurs in another setting. In a mice model of ovalbumin-induced allergic airway disease, 12-HHT and its companion cyclooxygenase metabolites,
3405:
873:, but also bound and was activated by a wide range of peptides, proteins, and other agents. BLT2 may ultimately prove to have binding specificity for a similarly broad range of agents.
2214:
Hicks, A; Monkarsh, S. P.; Hoffman, A. F.; Goodnow Jr, R (2007). "Leukotriene B4 receptor antagonists as therapeutics for inflammatory disease: Preclinical and clinical developments".
2391:
Matsunaga, Y; Fukuyama, S; Okuno, T; Sasaki, F; Matsunobu, T; Asai, Y; Matsumoto, K; Saeki, K; Oike, M; Sadamura, Y; Machida, K; Nakanishi, Y; Kubo, M; Yokomizo, T; Inoue, H (2013).
1876:"Characterization of the thromboxane synthase pathway product 12-oxoheptadeca-5(Z)-8(E)-10(E)-trienoic acid as a thromboxane A2 receptor antagonist with minimal intrinsic activity"
1702:"Mass determination of 15-hydroxyprostaglandin dehydrogenase from human placenta and kinetic studies with (5Z, 8E, 10E, 12S)-12-hydroxy-5,8,10-heptadecatrienoic acid as substrate"
1602:
Hecker, M; Ullrich, V (1988). "12(S)-Hydroxy-5,8,10 (Z,E,E)-heptadecatrienoic acid (HHT) is preferentially metabolized to its 12-keto derivative by human erythrocytes in vitro".
2152:
Anwar, Y; Sabir, J. S.; Qureshi, M. I.; Saini, K. S. (2014). "5-lipoxygenase: A promising drug target against inflammatory diseases-biochemical and pharmacological regulation".
865:
is a relevant and well-studied example of promiscuous receptors. Initially thought to be a second and low affinity receptor for the neutrophil tripeptide chemotactic factor,
712:); it did not, however, alter arachidonic acid metabolism in human platelets. Shortly thereafter, 12-HHT was reported to inhibit the chemotaxis-blocking effect of a human
913:
axis. Recent studies indicate that the role(s) of the 12-HHT/BLT2 receptor axis in human physiology and pathology may be very different from those of the LTB4/BLT1 axis.
737:
a receptor antagonist to moderate TXA2's action, respectively. This strategy may be essential for limiting the deleterious thrombotic and vasospastic activities of TXA2.
577:) metabolize PGG2 and PGH2 to 12-HHT and MDA. While the latter studies were conducted using recombinant cytochrome enzymes or sub-fractions of disrupted cells, the human
1038:
A large number of studies have associated BLT2 and, directly or by assumption, 12-HHT in the survival, growth, and/or spread of various human cancers. BLT2, also called
4097:
3398:
1777:
Campbell, P. B.; Tolson, T. A. (1988). "Modulation of human monocyte leukotactic responsiveness by thromboxane A2 and 12-hydroxyheptadecatrienoic acid (12-HHT)".
637:
287:
118:
3391:
261:
InChI=1S/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1
2535:
Liu, M; Saeki, K; Matsunobu, T; Okuno, T; Koga, T; Sugimoto, Y; Yokoyama, C; Nakamizo, S; Kabashima, K; Narumiya, S; Shimizu, T; Yokomizo, T (2014).
271:
InChI=1/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1
4467:
2944:
1330:"Xenobiotic-metabolizing cytochromes P450 convert prostaglandin endoperoxide to hydroxyheptadecatrienoic acid and the mutagen, malondialdehyde"
1027:
2341:"12(S)-Hydroxyheptadeca-5Z,8E,10E-trienoic acid suppresses UV-induced IL-6 synthesis in keratinocytes, exerting an anti-inflammatory activity"
2685:
524:
express cyclooxygenase and thromboxane synthase enzymes, producing PGG2, PGH2, and TXA2 in response to platelet aggregating agents such as
716:-derived factor on human moncytes while the immediate metabolite of 12-HHT, 12-oxo-HT, was reported to stimulate the chemotasis of human
3641:
3631:
671:
Acidic conditions (pH~1.1-1.5) cause 12-HHT to rearrange in a time- and temperature-dependent process to its 5-cis isomer, 12-hydroxy-5
1265:
252:
2440:
Singh, R. K.; Tandon, R; Dastidar, S. G.; Ray, A (2013). "A review on leukotrienes and their receptors with reference to asthma".
2103:
BΓ€ck, M; Powell, W. S.; DahlΓ©n, S. E.; Drazen, J. M.; Evans, J. F.; Serhan, C. N.; Shimizu, T; Yokomizo, T; Rovati, G. E. (2014).
4435:
3941:
3878:
3705:
2907:
2537:"12-Hydroxyheptadecatrienoic acid promotes epidermal wound healing by accelerating keratinocyte migration via the BLT2 receptor"
4275:
3621:
3478:
1118:
926:
12-HHT stimulates chemotactic responses in mouse bone marrow mast cells, which naturally express BLT2 receptors, as well as in
798:
4193:
4165:
4036:
3691:
3636:
1509:
John, H; Cammann, K; Schlegel, W (1998). "Development and review of radioimmunoassay of 12-S-hydroxyheptadecatrienoic acid".
1123:
810:
721:
179:
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Kaushal, M; Gopalan Kutty, N; Mallikarjuna Rao, C (2007). "Wound healing activity of NOE-aspirin: A pre-clinical study".
869:-formyl-met-leu-phe, subsequent studies showed that it was a high affinity receptor for the arachidonic acid metabolite,
359:
4460:
4175:
4137:
472:
of its three double bonds. The metabolite was for many years thought to be merely a biologically inactive byproduct of
3001:
3998:
1075:
761:
216:
987:
response to ovalbumin challenge. Finally, BLT2 receptor expression was significantly reduced in allergy-regulating
720:. and to inhibit platelet aggregation responses to various agents by stimulating platelets to raise their levels of
4420:
2300:"UVB radiation induces apoptosis in keratinocytes by activating a pathway linked to "BLT2-reactive oxygen species""
1019:
927:
403:
3602:
3459:
2678:
1102:
1065:
1039:
862:
1925:"A second leukotriene B(4) receptor, BLT2. A new therapeutic target in inflammation and immunological disorders"
581:, a form of blood circulating leukocyte, increases its expression of CYP2S1 when forced to differentiate into a
4366:
4334:
4213:
777:
537:
about one third of the total amount of arachidonic acid metabolites formed by physiologically stimulated human
640:
in a wide variety of human and other vertebrate cells to its 12-oxo (also termed 12-keto) derivative, 12-oxo-5
4302:
4112:
3445:
3428:
1107:
942:
757:
4356:
156:
4292:
1060:
652:-heptadecatrienoic acid (12-oxo-HHT or 12-keto-HHT). Pig kidney tissue also converted 12-HHT to 12-keto-5
4155:
4079:
3434:
3366:
3160:
3058:
2813:
909:
753:
709:
419:
2187:
Fourie, A. M. (2009). "Modulation of inflammatory disease by inhibitors of leukotriene A4 hydrolase".
4489:
4415:
4061:
3646:
3509:
3483:
2671:
1202:
1070:
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and accordingly are regarded primarily as contributing to the many human defensive and pathological (
725:
509:
50:
1827:"12(S)-Hydroxyheptadeca-5Z, 8E, 10E-trienoic acid is a natural ligand for leukotriene B4 receptor 2"
233:
37:
4107:
3103:
701:
469:
411:
84:
4250:
1546:"Thromboxane a synthase-independent production of 12-hydroxyheptadecatrienoic acid, a BLT2 ligand"
4230:
3420:
2514:
2465:
2422:
2239:
1905:
1802:
1488:
1023:
897:
780:. BLT1 receptor has a high degree of ligand-binding specificity: among a series of hydroxylated
590:
4084:
3853:
3833:
3828:
3818:
3798:
3783:
3773:
3582:
3552:
3527:
1248:
Wong, S. L.; Wong, W. T.; Tian, X. Y.; Lau, C. W.; Huang, Y (2010). "Prostaglandins in Action".
17:
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2414:
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1994:
1954:
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1395:
1351:
1310:
1271:
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1230:
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1085:
1080:
517:
476:
synthesis. More recent studies, however, have attached potentially important activity to it.
4255:
4026:
3868:
3838:
3587:
1700:
HΓΆhl, W; Stahl, B; Mundkowski, R; Hofmann, U; Meese, C. O.; Kuhlmann, U; Schlegel, W (1993).
138:
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4011:
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2404:
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2352:
2311:
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2124:
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2075:
2025:
1986:
1944:
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1846:
1838:
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1751:
1713:
1674:
1638:
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1557:
1518:
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1434:
1426:
1385:
1341:
1302:
1253:
1220:
1210:
1158:
964:
960:
773:
765:
586:
505:
493:
489:
407:
310:
1191:"Prostaglandin endoperoxides. Novel transformations of arachidonic acid in human platelets"
612:, rearranges non-enzymatically to a mixture of 12-HHT and 12-HHT's 8-cis isomer, i.e., 12-(
94:
2782:
1055:
1014:
769:
550:
450:
423:
237:
160:
2339:
Lee, J. W.; Ryu, H. C.; Ng, Y. C.; Kim, C; Wei, J. D.; Sabaratnam, V; Kim, J. H. (2012).
2257:
Miyata, A; Yokoyama, C; Ihara, H; Bandoh, S; Takeda, O; Takahashi, E; Tanabe, T (1994).
2014:"Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2"
1206:
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3740:
3732:
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3417:
3294:
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3217:
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2536:
2365:
2340:
2129:
2104:
1949:
1924:
1851:
1826:
1718:
1701:
1572:
1545:
1439:
1414:
1257:
1113:
749:
745:
733:
513:
353:
2165:
1990:
1522:
1390:
1373:
1225:
1190:
1163:
1146:
876:
The production of LTB4 and expression of BLT1 by human tissues are largely limited to
4483:
4410:
2727:
2275:
2258:
1977:
Tager, A. M.; Luster, A. D. (2003). "BLT1 and BLT2: The leukotriene B(4) receptors".
1892:
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951:
938:
794:
497:
473:
149:
2518:
2469:
2243:
1909:
760:
1 (BLT1 receptor) and its low affinity BLT2 receptor (Kd=23 nM); both receptors are
204:
4245:
4031:
3383:
3268:
3201:
3187:
2834:
2426:
1806:
1492:
1090:
1006:
988:
705:
697:
2501:
2484:
2453:
1874:
Ruf, A; Mundkowski, R; Siegle, I; Hofmann, U; Patscheke, H; Meese, C. O. (1998).
4425:
4074:
3863:
3808:
3414:
3086:
2891:
2857:
2393:"Leukotriene B4 receptor BLT2 negatively regulates allergic airway eosinophilia"
2227:
1010:
877:
2597:
1415:"Human CYP2S1 metabolizes cyclooxygenase- and lipoxygenase-derived eicosanoids"
1195:
Proceedings of the
National Academy of Sciences of the United States of America
532:
by feeding back to promote further aggregation of their cells of origin and as
4382:
4319:
4056:
3848:
3823:
3350:
2718:
2694:
2356:
1476:
1043:
893:
885:
881:
870:
781:
729:
717:
582:
338:
169:
129:
2636:
2105:"Update on leukotriene, lipoxin and oxoeicosanoid receptors: IUPHAR Review 7"
1825:
Okuno, T; Iizuka, Y; Okazaki, H; Yokomizo, T; Taguchi, R; Shimizu, T (2008).
1346:
1329:
4235:
4160:
4051:
4016:
3279:
1413:
Bui, P; Imaizumi, S; Beedanagari, S. R.; Reddy, S. T.; Hankinson, O (2011).
946:
901:
889:
594:
538:
533:
529:
521:
427:
415:
2654:
2605:
2570:
2510:
2461:
2418:
2374:
2325:
2259:"Characterization of the human gene (TBXAS1) encoding thromboxane synthase"
2235:
2200:
2173:
2138:
2089:
2039:
2030:
2013:
1998:
1958:
1860:
1581:
1484:
1448:
1430:
1355:
1328:
Plastaras, J. P.; Guengerich, F. P.; Nebert, D. W.; Marnett, L. J. (2000).
1275:
1215:
2284:
1940:
1901:
1798:
1763:
1727:
1686:
1650:
1615:
1530:
1399:
1314:
1234:
1172:
979:)-HETE) attained levels capable of activating BLT2 receptors. Also, BLT2
4387:
4351:
4265:
4198:
4089:
4046:
3753:
3542:
3238:
3041:
3033:
3025:
3017:
2552:
2409:
2392:
2316:
2299:
1842:
1790:
980:
955:
861:
isomers while the BLT2 receptor exhibits a promiscuous finding pattern.
713:
578:
525:
454:
2080:
2063:
1562:
3077:
3070:
3066:
1001:
972:
601:
191:
4098:
2120:
414:, and M. Hamberg, as a product of arachidonic acid metabolism made by
410:. It was discovered and structurally defined in 1973 by P. Wlodawer,
4324:
4127:
3981:
905:
605:
574:
570:
566:
562:
558:
554:
752:
enzyme pathway. It activates cells through both its high affinity (
352:
Except where otherwise noted, data are given for materials in their
3330:
2985:
1374:"On the mechanism of prostacyclin and thromboxane A2 biosynthesis"
934:
609:
117:
107:
2298:
Ryu, H. C.; Kim, C; Kim, J. Y.; Chung, J. H.; Kim, J. H. (2010).
813:). The BLT2 receptor's relative affinities for finding LTB4, 12(
2485:"A turn on and a turn off: BLT1 and BLT2 mechanisms in the lung"
1923:
Yokomizo, T; Kato, K; Terawaki, K; Izumi, T; Shimizu, T (2000).
501:
3387:
2667:
1147:"On the organization and mechanism of prostaglandin synthetase"
2663:
2012:
Yokomizo, T; Kato, K; Hagiya, H; Izumi, T; Shimizu, T (2001).
1046:(malignant behavior of tumor cells) in the following cancers:
668:-heptadecadienoic acid) and 12-hydroxy-heptadecadienoic acid.
496:
metabolize arachidonic acid to the 15-hydroperoxy, 20 carbon
221:
950:
Furthermore, 12-HHT inhibits HaCaT cells from synthesizing
1252:. Advances in Pharmacology. Vol. 60. pp. 61β83.
748:(i.e. LTB4) is an arachidonic acid metabolite made by the
516:, the 17 carbon product, 12-HHT, and the 3 carbon product
1544:
Matsunobu, T; Okuno, T; Yokoyama, C; Yokomizo, T (2013).
945:
which in turn cause the HaCaT cells to die by activating
933:
On the other hand, the immortalized human skin cell line
764:
that, when ligand-bound, activate cells by releasing the
3942:
3879:
3706:
1979:
Prostaglandins, Leukotrienes, and
Essential Fatty Acids
4103:
3692:
2064:"Two distinct leukotriene B4 receptors, BLT1 and BLT2"
1042:, is closely associated with 12-HHT in stimulation of
504:, and then to the 15-hydroxy, 20 carbon intermediate,
853:-eicosatetraenoic acid (i.e. LTB4) but not LTB4's 12(
4276:
4176:
4138:
1013:
model of obesity, diabetes, and dyslipidemia due to
4400:
4365:
4333:
4301:
4274:
4212:
4174:
4136:
3999:
3997:
3980:
3940:
3877:
3704:
3690:
3601:
3458:
3444:
3427:
3095:
3057:
3010:
2994:
2984:
2943:
2916:
2900:
2890:
2856:
2827:
2781:
2762:
2755:
2736:
2726:
2717:
2701:
512:further metabolizes PGH2 to the 20 carbon product,
178:
3603:
3460:
1250:Cardiovascular Pharmacology - Endothelial Control
917:Recent studies on 12-HHT/BLT2 receptor activities
4367:
4335:
4214:
203:
4303:
3446:
2530:
2528:
2386:
2384:
2057:
2055:
2053:
2051:
2049:
1972:
1970:
1968:
1820:
1818:
1816:
93:
1597:
1595:
1593:
1591:
3399:
2679:
2621:"Time heals all wounds--but 12-HHT is faster"
1504:
1502:
1367:
1365:
1287:
1285:
1184:
1182:
1140:
1138:
402:) is a 17 carbon metabolite of the 20 carbon
8:
638:15-hydroxyprostaglandin dehydrogenase (NAD+)
4436:5-HPETE (arachidonic acid 5-hydroperoxide)
3994:
3701:
3455:
3441:
3406:
3392:
3384:
2991:
2897:
2759:
2733:
2723:
2686:
2672:
2664:
2483:Watanabe, M; Machida, K; Inoue, H (2014).
1511:Prostaglandins & Other Lipid Mediators
236:
159:
137:
71:)-12-Hydroxyheptadeca-5,8,10-trienoic acid
29:
2644:
2560:
2500:
2408:
2364:
2315:
2274:
2128:
2079:
2029:
1948:
1891:
1850:
1717:
1571:
1561:
1438:
1389:
1345:
1224:
1214:
1162:
937:expresses BLT2 receptors and responds to
430:. 12-HHT is less ambiguously termed 12-(
3950:Tooltip Cysteinyl leukotriene receptor E
3887:Tooltip Cysteinyl leukotriene receptor 2
3714:Tooltip Cysteinyl leukotriene receptor 1
2189:Current Opinion in Investigational Drugs
446:-heptadecatrienoic acid to indicate the
2216:Expert Opinion on Investigational Drugs
1631:Archives of Biochemistry and Biophysics
1134:
292:
257:
232:
3697:Tooltip Cysteinyl leukotriene receptor
2619:Gus-Brautbar, Y; Panigrahy, D (2014).
1028:non-steroidal anti-inflammatory agents
809:)-HETE (i.e. the two stereoisomers of
600:PGH2, particularly in the presence of
150:
2489:Expert Review of Respiratory Medicine
2345:Experimental & Molecular Medicine
264:Key: KUKJHGXXZWHSBG-WBGSEQOASA-N
7:
4285:Tooltip Leukotriene B4 Ο-hydroxylase
4181:Tooltip Arachidonate 15-lipoxygenase
4143:Tooltip Arachidonate 12-lipoxygenase
2625:The Journal of Experimental Medicine
2541:The Journal of Experimental Medicine
2304:Journal of Investigative Dermatology
1929:The Journal of Experimental Medicine
1831:The Journal of Experimental Medicine
941:(UVB) radiation by generating toxic
687:Activities and clinical significance
4004:Tooltip Arachidonate 5-lipoxygenase
1378:The Journal of Biological Chemistry
1334:The Journal of Biological Chemistry
1151:The Journal of Biological Chemistry
1145:Wlodawer, P; Samuelsson, B (1973).
700:I2 (PGI2), a powerful inhibitor of
274:Key: KUKJHGXXZWHSBG-WBGSEQOABE
194:
1719:10.1111/j.1432-1033.1993.tb17897.x
1258:10.1016/B978-0-12-385061-4.00003-9
1189:Hamberg, M; Samuelsson, B (1974).
25:
4416:Ξ³-Linolenic acid (gamolenic acid)
4070:Meclofenamic acid (meclofenamate)
3611:Tooltip Leukotriene B4 receptor 2
3468:Tooltip Leukotriene B4 receptor 1
3002:Arachidonic acid 15-hydroperoxide
2166:10.2174/1389450114666131209110745
741:12-HHT is a BLT2 receptor agonist
636:12-HHT is further metabolized by
31:12-Hydroxyheptadecatrienoic acid
4375:Tooltip Leukotriene D4 hydrolase
4344:Tooltip Leukotriene C4 hydrolase
4223:Tooltip Leukotriene A4 hydrolase
2908:Arachidonic acid 5-hydroperoxide
2276:10.1111/j.1432-1033.1994.00273.x
2263:European Journal of Biochemistry
1893:10.1046/j.1365-2141.1998.00669.x
1706:European Journal of Biochemistry
660:-heptadecadienoic acid (12-oxo-5
372:12-Hydroxyheptadecatrienoic acid
322:
295:CCCCC(/C=C/C=C/C/C=C\CCCC(=O)O)O
36:
18:12-hydroxyheptadecatrienoic acid
4468:Prostanoid signaling modulators
4312:Tooltip Leukotriene C4 synthase
3451:Tooltip Leukotriene B4 receptor
2109:British Journal of Pharmacology
2018:Journal of Biological Chemistry
1419:Drug Metabolism and Disposition
1119:12-Hydroxyeicosatetraenoic acid
799:12-Hydroxyeicosatetraenoic acid
356:(at 25 Β°C , 100 kPa).
1880:British Journal of Haematology
1372:Hecker, M; Ullrich, V (1989).
1124:15-hydroxyicosatetraenoic acid
811:15-Hydroxyicosatetraenoic acid
722:Cyclic adenosine monophosphate
328:
316:
1:
4461:Receptor/signaling modulators
1991:10.1016/s0952-3278(03)00073-5
1550:The Journal of Lipid Research
1523:10.1016/s0090-6980(98)00043-4
1391:10.1016/S0021-9258(17)31235-8
1164:10.1016/S0021-9258(19)43558-8
2502:10.1586/17476348.2014.908715
2454:10.3109/02770903.2013.823447
1779:Journal of Leukocyte Biology
1756:10.1016/0003-2697(90)90115-p
1679:10.1016/0006-2952(87)90241-3
1643:10.1016/0003-9861(87)90589-3
1465:Basic Research in Cardiology
1307:10.1016/0090-6980(87)90297-8
2839:(Prostacyclin/Epoprostenol)
2228:10.1517/13543784.16.12.1909
1076:Transitional cell carcinoma
954:(IL-6), a pro-inflammatory
928:Chinese hamster ovary cells
880:-derived cells such as the
762:G protein coupled receptors
528:; these metabolites act as
426:glands and by intact human
4506:
2598:10.1016/j.niox.2006.07.004
404:polyunsaturated fatty acid
4452:
2357:10.3858/emm.2012.44.6.043
1477:10.1007/s00395-012-0319-8
1103:Leukotriene B4 receptor 2
1066:Follicular thyroid cancer
1040:leukotriene B4 receptor 2
983:mice exhibited a greatly
863:Formyl peptide receptor 2
778:Heterotrimeric G proteins
683:-heptadecatrienoic acid.
350:
303:
283:
248:
77:
49:
44:
35:
2637:10.1084/jem.2116insight1
1667:Biochemical Pharmacology
1347:10.1074/jbc.275.16.11784
922:Inflammation and allergy
892:, and various types of
4421:Dihomo-Ξ³-linolenic acid
2068:Journal of Biochemistry
1744:Analytical Biochemistry
1108:Leukotriene B4 receptor
1020:tumor necrosis factor Ξ±
943:reactive oxygen species
758:Leukotriene B4 receptor
2031:10.1074/jbc.M011361200
1431:10.1124/dmd.110.035121
1216:10.1073/pnas.71.9.3400
1061:Urinary bladder cancer
910:inflammatory responses
422:) isolated from sheep
4357:Serine-borate complex
3523:CGS-23131 (LY-223982)
1941:10.1084/jem.192.3.421
793:)-HETE (i.e. the two
754:Dissociation constant
710:Prostacyclin synthase
420:endoplasmic reticulum
4293:17-Octadecynoic acid
4063:Hypericum perforatum
2553:10.1084/jem.20132063
2410:10.1096/fj.12-217000
2317:10.1038/jid.2009.436
2154:Current Drug Targets
2062:Yokomizo, T (2015).
1843:10.1084/jem.20072329
1791:10.1002/jlb.43.2.117
1071:Renal cell carcinoma
726:Thromboxane receptor
510:Thromboxane synthase
384:)-hydroxyheptadeca-5
51:Preferred IUPAC name
4388:Ubenimex (bestatin)
4266:Ubenimex (bestatin)
3104:bronchoconstriction
1563:10.1194/jlr.M037754
1207:1974PNAS...71.3400H
702:platelet activation
500:(PG) intermediate,
470:cis-trans isomerism
412:Bengt I. Samuelsson
346: gΒ·mol
32:
4156:3-Methoxytropolone
4080:N-Stearoyldopamine
1024:metalloproteinases
971:) stereoisomer of
898:ulcerative colitis
704:and stimulator of
632:Further metabolism
591:lipopolysaccharide
360:Infobox references
30:
4477:
4476:
4396:
4395:
4065:(St. John's Wort)
3991:
3976:
3975:
3972:
3971:
3686:
3685:
3438:
3381:
3380:
3053:
3052:
2980:
2979:
2886:
2885:
2852:
2851:
2848:
2847:
2442:Journal of Asthma
2397:The FASEB Journal
2121:10.1111/bph.12665
2081:10.1093/jb/mvu078
1086:Pancreatic cancer
1081:Esophageal cancer
608:iron (FeIII), or
518:malonyldialdehyde
368:Chemical compound
366:
365:
217:CompTox Dashboard
119:Interactive image
27:Chemical compound
16:(Redirected from
4497:
4431:Arachidonic acid
4376:
4372:
4345:
4341:
4313:
4309:
4286:
4282:
4224:
4220:
4182:
4178:
4144:
4140:
4104:
4100:
4005:
4001:
3995:
3985:
3951:
3947:
3888:
3884:
3715:
3711:
3702:
3698:
3694:
3612:
3608:
3469:
3465:
3456:
3452:
3448:
3442:
3432:
3408:
3401:
3394:
3385:
3155:vasoconstriction
2992:
2898:
2760:
2734:
2724:
2709:Arachidonic acid
2688:
2681:
2674:
2665:
2659:
2658:
2648:
2616:
2610:
2609:
2581:
2575:
2574:
2564:
2532:
2523:
2522:
2504:
2480:
2474:
2473:
2437:
2431:
2430:
2412:
2388:
2379:
2378:
2368:
2336:
2330:
2329:
2319:
2295:
2289:
2288:
2278:
2254:
2248:
2247:
2211:
2205:
2204:
2184:
2178:
2177:
2149:
2143:
2142:
2132:
2100:
2094:
2093:
2083:
2059:
2044:
2043:
2033:
2009:
2003:
2002:
1974:
1963:
1962:
1952:
1920:
1914:
1913:
1895:
1871:
1865:
1864:
1854:
1822:
1811:
1810:
1774:
1768:
1767:
1738:
1732:
1731:
1721:
1697:
1691:
1690:
1673:(11): 1799β805.
1661:
1655:
1654:
1626:
1620:
1619:
1599:
1586:
1585:
1575:
1565:
1541:
1535:
1534:
1506:
1497:
1496:
1459:
1453:
1452:
1442:
1410:
1404:
1403:
1393:
1369:
1360:
1359:
1349:
1340:(16): 11784β90.
1325:
1319:
1318:
1289:
1280:
1279:
1245:
1239:
1238:
1228:
1218:
1186:
1177:
1176:
1166:
1142:
965:Prostaglandin D2
961:Prostaglandin E2
774:Gi alpha subunit
766:Gq alpha subunit
587:interferon gamma
506:prostaglandin H2
494:cyclooxygenase-2
490:Cyclooxygenase-1
457:residue and the
408:arachidonic acid
345:
330:
324:
318:
311:Chemical formula
241:
240:
225:
223:
207:
196:
182:
163:
152:
141:
121:
97:
40:
33:
21:
4505:
4504:
4500:
4499:
4498:
4496:
4495:
4494:
4480:
4479:
4478:
4473:
4448:
4444:
4392:
4374:
4371:
4361:
4343:
4339:
4329:
4311:
4307:
4297:
4284:
4280:
4270:
4222:
4218:
4208:
4180:
4170:
4142:
4132:
4102:
4003:
3984:
3968:
3964:
3949:
3946:
3936:
3917:
3909:
3901:
3886:
3883:
3873:
3744:
3736:
3728:
3713:
3710:
3696:
3682:
3658:
3650:
3610:
3607:
3597:
3513:
3495:
3487:
3467:
3464:
3450:
3431:
3423:
3412:
3382:
3377:
3370:
3361:
3341:
3321:
3313:
3298:
3290:
3272:
3264:
3249:
3229:
3221:
3213:
3205:
3197:
3180:
3172:
3164:
3145:
3137:
3129:
3121:
3113:
3091:
3081:
3074:
3049:
3045:
3037:
3029:
3021:
3006:
2976:
2972:
2964:
2956:
2939:
2935:
2927:
2912:
2882:
2878:
2870:
2844:
2838:
2823:
2817:
2806:
2795:
2777:
2773:
2751:
2747:
2713:
2697:
2692:
2662:
2618:
2617:
2613:
2583:
2582:
2578:
2534:
2533:
2526:
2482:
2481:
2477:
2439:
2438:
2434:
2390:
2389:
2382:
2338:
2337:
2333:
2310:(4): 1095β106.
2297:
2296:
2292:
2256:
2255:
2251:
2222:(12): 1909β20.
2213:
2212:
2208:
2195:(11): 1173β82.
2186:
2185:
2181:
2151:
2150:
2146:
2115:(15): 3551β74.
2102:
2101:
2097:
2061:
2060:
2047:
2024:(15): 12454β9.
2011:
2010:
2006:
1985:(2β3): 123β34.
1976:
1975:
1966:
1922:
1921:
1917:
1873:
1872:
1868:
1824:
1823:
1814:
1776:
1775:
1771:
1740:
1739:
1735:
1699:
1698:
1694:
1663:
1662:
1658:
1628:
1627:
1623:
1601:
1600:
1589:
1556:(11): 2979β87.
1543:
1542:
1538:
1508:
1507:
1500:
1461:
1460:
1456:
1412:
1411:
1407:
1371:
1370:
1363:
1327:
1326:
1322:
1291:
1290:
1283:
1268:
1247:
1246:
1242:
1188:
1187:
1180:
1144:
1143:
1136:
1132:
1099:
1056:Prostate cancer
1036:
1015:leptin receptor
998:
924:
919:
805:)-HpETE and 15(
770:pertussis toxin
756:of 0.5-1.5 nM)
743:
694:
689:
634:
551:cytochrome P450
547:
487:
482:
451:stereoisomerism
424:seminal vesicle
369:
362:
357:
343:
333:
327:
321:
313:
299:
296:
291:
290:
279:
276:
275:
272:
266:
265:
262:
256:
255:
244:
226:
219:
210:
197:
185:
172:
144:
124:
111:
100:
87:
73:
72:
28:
23:
22:
15:
12:
11:
5:
4503:
4501:
4493:
4492:
4482:
4481:
4475:
4474:
4472:
4471:
4464:
4457:
4453:
4450:
4449:
4447:
4446:
4442:
4438:
4433:
4428:
4426:Diacylglycerol
4423:
4418:
4413:
4404:
4402:
4398:
4397:
4394:
4393:
4391:
4390:
4385:
4379:
4377:
4369:
4363:
4362:
4360:
4359:
4354:
4348:
4346:
4337:
4331:
4330:
4328:
4327:
4322:
4316:
4314:
4305:
4299:
4298:
4296:
4295:
4289:
4287:
4278:
4272:
4271:
4269:
4268:
4263:
4258:
4253:
4248:
4243:
4238:
4233:
4227:
4225:
4216:
4210:
4209:
4207:
4206:
4201:
4196:
4191:
4185:
4183:
4172:
4171:
4169:
4168:
4163:
4158:
4153:
4147:
4145:
4134:
4133:
4131:
4130:
4125:
4120:
4115:
4110:
4093:
4092:
4087:
4082:
4077:
4072:
4067:
4059:
4054:
4049:
4044:
4039:
4034:
4029:
4024:
4019:
4014:
4008:
4006:
3992:
3978:
3977:
3974:
3973:
3970:
3969:
3967:
3966:
3962:
3954:
3952:
3944:
3938:
3937:
3935:
3934:
3929:
3920:
3919:
3915:
3911:
3907:
3903:
3899:
3891:
3889:
3881:
3875:
3874:
3872:
3871:
3866:
3861:
3856:
3851:
3846:
3841:
3836:
3831:
3826:
3821:
3816:
3811:
3806:
3801:
3796:
3791:
3786:
3781:
3776:
3771:
3766:
3761:
3756:
3747:
3746:
3742:
3738:
3734:
3730:
3726:
3718:
3716:
3708:
3699:
3688:
3687:
3684:
3683:
3681:
3680:
3675:
3670:
3661:
3660:
3656:
3652:
3648:
3647:20-Hydroxy-LTB
3644:
3639:
3634:
3629:
3624:
3615:
3613:
3605:
3599:
3598:
3596:
3595:
3590:
3585:
3580:
3575:
3570:
3565:
3560:
3555:
3550:
3545:
3540:
3535:
3530:
3525:
3520:
3515:
3511:
3510:20-Carboxy-LTB
3503:
3502:
3497:
3493:
3489:
3485:
3484:20-Hydroxy-LTB
3481:
3472:
3470:
3462:
3453:
3439:
3425:
3424:
3413:
3411:
3410:
3403:
3396:
3388:
3379:
3378:
3376:
3375:
3374:
3373:
3368:
3364:
3363:(Dinoprostone)
3359:
3346:
3345:
3344:
3343:
3339:
3326:
3325:
3324:
3323:
3319:
3315:
3311:
3302:
3301:
3300:
3296:
3292:
3288:
3276:
3275:
3274:
3270:
3266:
3262:
3253:
3252:
3251:
3247:
3234:
3233:
3232:
3231:
3227:
3223:
3219:
3215:
3211:
3207:
3203:
3199:
3195:
3184:
3183:
3182:
3178:
3174:
3170:
3166:
3162:
3150:
3149:
3148:
3147:
3143:
3139:
3135:
3131:
3127:
3123:
3119:
3115:
3111:
3099:
3097:
3093:
3092:
3090:
3089:
3084:
3079:
3072:
3063:
3061:
3055:
3054:
3051:
3050:
3048:
3047:
3043:
3039:
3035:
3031:
3027:
3023:
3019:
3014:
3012:
3008:
3007:
3005:
3004:
2998:
2996:
2989:
2982:
2981:
2978:
2977:
2975:
2974:
2970:
2966:
2962:
2958:
2954:
2949:
2947:
2941:
2940:
2938:
2937:
2933:
2929:
2925:
2920:
2918:
2914:
2913:
2911:
2910:
2904:
2902:
2895:
2888:
2887:
2884:
2883:
2881:
2880:
2876:
2872:
2868:
2863:
2861:
2854:
2853:
2850:
2849:
2846:
2845:
2843:
2842:
2836:
2831:
2829:
2825:
2824:
2822:
2821:
2815:
2810:
2809:
2804:
2799:
2798:
2796:(Dinoprostone)
2793:
2788:
2786:
2779:
2778:
2776:
2775:
2771:
2766:
2764:
2757:
2753:
2752:
2750:
2749:
2745:
2740:
2738:
2731:
2728:Prostaglandins
2721:
2715:
2714:
2712:
2711:
2705:
2703:
2699:
2698:
2693:
2691:
2690:
2683:
2676:
2668:
2661:
2660:
2611:
2576:
2547:(6): 1063β78.
2524:
2475:
2432:
2403:(8): 3306β14.
2380:
2331:
2290:
2249:
2206:
2179:
2144:
2095:
2045:
2004:
1964:
1915:
1866:
1812:
1769:
1733:
1692:
1656:
1621:
1587:
1536:
1517:(2β3): 53β76.
1498:
1454:
1405:
1361:
1320:
1295:Prostaglandins
1281:
1266:
1240:
1178:
1157:(16): 5673β8.
1133:
1131:
1128:
1127:
1126:
1121:
1116:
1114:Leukotriene B4
1111:
1105:
1098:
1095:
1094:
1093:
1088:
1083:
1078:
1073:
1068:
1063:
1058:
1053:
1035:
1032:
997:
994:
923:
920:
918:
915:
789:)-HETE and 12(
750:5-lipoxygenase
746:Leukotriene B4
742:
739:
734:blood clotting
693:
690:
688:
685:
633:
630:
553:enzymes (e.g.
546:
543:
514:Thromboxane A2
486:
485:Primary source
483:
481:
478:
396:-trienoic acid
367:
364:
363:
358:
354:standard state
351:
348:
347:
341:
335:
334:
331:
325:
319:
314:
309:
306:
305:
301:
300:
298:
297:
294:
286:
285:
284:
281:
280:
278:
277:
273:
270:
269:
267:
263:
260:
259:
251:
250:
249:
246:
245:
243:
242:
234:DTXSID50969517
229:
227:
215:
212:
211:
209:
208:
200:
198:
190:
187:
186:
184:
183:
175:
173:
168:
165:
164:
154:
146:
145:
143:
142:
134:
132:
126:
125:
123:
122:
114:
112:
105:
102:
101:
99:
98:
90:
88:
83:
80:
79:
75:
74:
54:
53:
47:
46:
42:
41:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
4502:
4491:
4488:
4487:
4485:
4470:
4469:
4465:
4463:
4462:
4458:
4455:
4454:
4451:
4445:
4441:Leukotriene A
4439:
4437:
4434:
4432:
4429:
4427:
4424:
4422:
4419:
4417:
4414:
4412:
4411:Linoleic acid
4409:
4406:
4405:
4403:
4399:
4389:
4386:
4384:
4381:
4380:
4378:
4373:
4364:
4358:
4355:
4353:
4350:
4349:
4347:
4342:
4332:
4326:
4323:
4321:
4318:
4317:
4315:
4310:
4300:
4294:
4291:
4290:
4288:
4283:
4273:
4267:
4264:
4262:
4259:
4257:
4254:
4252:
4249:
4247:
4244:
4242:
4239:
4237:
4234:
4232:
4229:
4228:
4226:
4221:
4211:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4186:
4184:
4179:
4173:
4167:
4164:
4162:
4159:
4157:
4154:
4152:
4149:
4148:
4146:
4141:
4135:
4129:
4126:
4124:
4121:
4119:
4116:
4114:
4111:
4109:
4106:
4101:
4095:
4094:
4091:
4088:
4086:
4083:
4081:
4078:
4076:
4073:
4071:
4068:
4066:
4064:
4060:
4058:
4055:
4053:
4050:
4048:
4045:
4043:
4040:
4038:
4035:
4033:
4030:
4028:
4025:
4023:
4020:
4018:
4015:
4013:
4010:
4009:
4007:
4002:
3996:
3993:
3989:
3983:
3979:
3965:
3961:Leukotriene E
3959:
3956:
3955:
3953:
3948:
3939:
3933:
3930:
3928:
3925:
3922:
3921:
3918:
3914:Leukotriene E
3912:
3910:
3906:Leukotriene D
3904:
3902:
3898:Leukotriene C
3896:
3893:
3892:
3890:
3885:
3876:
3870:
3867:
3865:
3862:
3860:
3857:
3855:
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3835:
3832:
3830:
3827:
3825:
3822:
3820:
3817:
3815:
3812:
3810:
3807:
3805:
3802:
3800:
3797:
3795:
3792:
3790:
3787:
3785:
3782:
3780:
3777:
3775:
3772:
3770:
3767:
3765:
3762:
3760:
3757:
3755:
3752:
3749:
3748:
3745:
3741:Leukotriene E
3739:
3737:
3733:Leukotriene D
3731:
3729:
3725:Leukotriene C
3723:
3720:
3719:
3717:
3712:
3703:
3700:
3695:
3689:
3679:
3676:
3674:
3671:
3669:
3666:
3663:
3662:
3659:
3655:Leukotriene B
3653:
3651:
3645:
3643:
3640:
3638:
3635:
3633:
3630:
3628:
3625:
3623:
3620:
3617:
3616:
3614:
3609:
3600:
3594:
3591:
3589:
3586:
3584:
3581:
3579:
3576:
3574:
3571:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3531:
3529:
3526:
3524:
3521:
3519:
3516:
3514:
3508:
3505:
3504:
3501:
3498:
3496:
3492:Leukotriene B
3490:
3488:
3482:
3480:
3477:
3474:
3473:
3471:
3466:
3457:
3454:
3449:
3443:
3440:
3436:
3430:
3426:
3422:
3419:
3416:
3409:
3404:
3402:
3397:
3395:
3390:
3389:
3386:
3371:
3365:
3362:
3356:
3355:
3354:
3352:
3348:
3347:
3342:
3336:
3335:
3334:
3332:
3328:
3327:
3322:
3316:
3314:
3308:
3307:
3306:
3303:
3299:
3293:
3291:
3285:
3284:
3283:
3281:
3277:
3273:
3267:
3265:
3259:
3258:
3257:
3254:
3250:
3244:
3243:
3242:
3240:
3236:
3235:
3230:
3224:
3222:
3216:
3214:
3208:
3206:
3200:
3198:
3192:
3191:
3190:
3189:
3185:
3181:
3175:
3173:
3167:
3165:
3159:
3158:
3157:
3156:
3152:
3151:
3146:
3140:
3138:
3132:
3130:
3124:
3122:
3116:
3114:
3108:
3107:
3106:
3105:
3101:
3100:
3098:
3094:
3088:
3085:
3082:
3075:
3068:
3065:
3064:
3062:
3060:
3056:
3046:
3040:
3038:
3032:
3030:
3024:
3022:
3016:
3015:
3013:
3009:
3003:
3000:
2999:
2997:
2993:
2990:
2987:
2983:
2973:
2967:
2965:
2959:
2957:
2951:
2950:
2948:
2946:
2942:
2936:
2930:
2928:
2922:
2921:
2919:
2915:
2909:
2906:
2905:
2903:
2899:
2896:
2893:
2889:
2879:
2873:
2871:
2865:
2864:
2862:
2859:
2855:
2840:
2833:
2832:
2830:
2826:
2819:
2812:
2811:
2808:
2807:(Alprostadil)
2801:
2800:
2797:
2790:
2789:
2787:
2784:
2780:
2774:
2768:
2767:
2765:
2761:
2758:
2754:
2748:
2742:
2741:
2739:
2735:
2732:
2729:
2725:
2722:
2720:
2716:
2710:
2707:
2706:
2704:
2700:
2696:
2689:
2684:
2682:
2677:
2675:
2670:
2669:
2666:
2656:
2652:
2647:
2642:
2638:
2634:
2630:
2626:
2622:
2615:
2612:
2607:
2603:
2599:
2595:
2591:
2587:
2580:
2577:
2572:
2568:
2563:
2558:
2554:
2550:
2546:
2542:
2538:
2531:
2529:
2525:
2520:
2516:
2512:
2508:
2503:
2498:
2494:
2490:
2486:
2479:
2476:
2471:
2467:
2463:
2459:
2455:
2451:
2448:(9): 922β31.
2447:
2443:
2436:
2433:
2428:
2424:
2420:
2416:
2411:
2406:
2402:
2398:
2394:
2387:
2385:
2381:
2376:
2372:
2367:
2362:
2358:
2354:
2351:(6): 378β86.
2350:
2346:
2342:
2335:
2332:
2327:
2323:
2318:
2313:
2309:
2305:
2301:
2294:
2291:
2286:
2282:
2277:
2272:
2268:
2264:
2260:
2253:
2250:
2245:
2241:
2237:
2233:
2229:
2225:
2221:
2217:
2210:
2207:
2202:
2198:
2194:
2190:
2183:
2180:
2175:
2171:
2167:
2163:
2160:(4): 410β22.
2159:
2155:
2148:
2145:
2140:
2136:
2131:
2126:
2122:
2118:
2114:
2110:
2106:
2099:
2096:
2091:
2087:
2082:
2077:
2073:
2069:
2065:
2058:
2056:
2054:
2052:
2050:
2046:
2041:
2037:
2032:
2027:
2023:
2019:
2015:
2008:
2005:
2000:
1996:
1992:
1988:
1984:
1980:
1973:
1971:
1969:
1965:
1960:
1956:
1951:
1946:
1942:
1938:
1935:(3): 421β32.
1934:
1930:
1926:
1919:
1916:
1911:
1907:
1903:
1899:
1894:
1889:
1885:
1881:
1877:
1870:
1867:
1862:
1858:
1853:
1848:
1844:
1840:
1837:(4): 759β66.
1836:
1832:
1828:
1821:
1819:
1817:
1813:
1808:
1804:
1800:
1796:
1792:
1788:
1785:(2): 117β24.
1784:
1780:
1773:
1770:
1765:
1761:
1757:
1753:
1749:
1745:
1737:
1734:
1729:
1725:
1720:
1715:
1711:
1707:
1703:
1696:
1693:
1688:
1684:
1680:
1676:
1672:
1668:
1660:
1657:
1652:
1648:
1644:
1640:
1637:(2): 444β50.
1636:
1632:
1625:
1622:
1617:
1613:
1609:
1605:
1598:
1596:
1594:
1592:
1588:
1583:
1579:
1574:
1569:
1564:
1559:
1555:
1551:
1547:
1540:
1537:
1532:
1528:
1524:
1520:
1516:
1512:
1505:
1503:
1499:
1494:
1490:
1486:
1482:
1478:
1474:
1470:
1466:
1458:
1455:
1450:
1446:
1441:
1436:
1432:
1428:
1425:(2): 180β90.
1424:
1420:
1416:
1409:
1406:
1401:
1397:
1392:
1387:
1384:(1): 141β50.
1383:
1379:
1375:
1368:
1366:
1362:
1357:
1353:
1348:
1343:
1339:
1335:
1331:
1324:
1321:
1316:
1312:
1308:
1304:
1301:(5): 749β63.
1300:
1296:
1288:
1286:
1282:
1277:
1273:
1269:
1267:9780123850614
1263:
1259:
1255:
1251:
1244:
1241:
1236:
1232:
1227:
1222:
1217:
1212:
1208:
1204:
1201:(9): 3400β4.
1200:
1196:
1192:
1185:
1183:
1179:
1174:
1170:
1165:
1160:
1156:
1152:
1148:
1141:
1139:
1135:
1129:
1125:
1122:
1120:
1117:
1115:
1112:
1109:
1106:
1104:
1101:
1100:
1096:
1092:
1089:
1087:
1084:
1082:
1079:
1077:
1074:
1072:
1069:
1067:
1064:
1062:
1059:
1057:
1054:
1052:
1051:Breast cancer
1049:
1048:
1047:
1045:
1041:
1033:
1031:
1029:
1025:
1021:
1016:
1012:
1008:
1003:
996:Wound healing
995:
993:
990:
986:
982:
978:
974:
970:
966:
962:
957:
953:
952:interleukin-6
948:
944:
940:
939:ultraviolet B
936:
931:
929:
921:
916:
914:
911:
907:
903:
899:
895:
891:
887:
883:
879:
874:
872:
868:
864:
860:
856:
852:
848:
844:
840:
837:)-dihydroxy-6
836:
832:
828:
824:
820:
816:
812:
808:
804:
800:
796:
795:stereoisomers
792:
788:
783:
779:
775:
771:
767:
763:
759:
755:
751:
747:
740:
738:
735:
731:
727:
723:
719:
715:
711:
707:
703:
699:
692:Early studies
691:
686:
684:
682:
678:
674:
669:
667:
663:
659:
655:
651:
647:
643:
639:
631:
629:
627:
623:
619:
615:
611:
607:
604:iron (FeII),
603:
598:
596:
592:
588:
585:phenotype by
584:
580:
576:
572:
568:
564:
560:
556:
552:
545:Other sources
544:
542:
540:
535:
531:
527:
523:
519:
515:
511:
507:
503:
499:
498:prostaglandin
495:
491:
484:
479:
477:
475:
474:prostaglandin
471:
468:
464:
460:
456:
452:
449:
445:
441:
437:
433:
429:
425:
421:
417:
413:
409:
405:
401:
397:
395:
391:
387:
383:
377:
374:(also termed
373:
361:
355:
349:
342:
340:
337:
336:
315:
312:
308:
307:
302:
293:
289:
282:
268:
258:
254:
247:
239:
235:
231:
230:
228:
218:
214:
213:
206:
202:
201:
199:
193:
189:
188:
181:
177:
176:
174:
171:
167:
166:
162:
158:
155:
153:
151:ECHA InfoCard
148:
147:
140:
136:
135:
133:
131:
128:
127:
120:
116:
115:
113:
109:
104:
103:
96:
92:
91:
89:
86:
82:
81:
76:
70:
66:
62:
58:
52:
48:
43:
39:
34:
19:
4466:
4459:
4407:
4251:JNJ-26993135
4246:Fosinoprilat
4096:
4062:
4032:Caffeic acid
3957:
3924:Antagonists:
3923:
3894:
3751:Antagonists:
3750:
3721:
3665:Antagonists:
3664:
3626:
3618:
3507:Antagonists:
3506:
3475:
3353:stimulation:
3349:
3333:stimulation:
3329:
3304:
3278:
3255:
3237:
3188:vasodilation
3186:
3153:
3102:
2892:Leukotrienes
2858:Thromboxanes
2628:
2624:
2614:
2592:(1): 150β6.
2589:
2586:Nitric Oxide
2585:
2579:
2544:
2540:
2495:(4): 381β3.
2492:
2488:
2478:
2445:
2441:
2435:
2400:
2396:
2348:
2344:
2334:
2307:
2303:
2293:
2269:(2): 273β9.
2266:
2262:
2252:
2219:
2215:
2209:
2192:
2188:
2182:
2157:
2153:
2147:
2112:
2108:
2098:
2074:(2): 65β71.
2071:
2067:
2021:
2017:
2007:
1982:
1978:
1932:
1928:
1918:
1886:(1): 59β65.
1883:
1879:
1869:
1834:
1830:
1782:
1778:
1772:
1750:(2): 244β8.
1747:
1743:
1736:
1712:(1): 67β73.
1709:
1705:
1695:
1670:
1666:
1659:
1634:
1630:
1624:
1610:(1): 19β25.
1607:
1603:
1553:
1549:
1539:
1514:
1510:
1468:
1464:
1457:
1422:
1418:
1408:
1381:
1377:
1337:
1333:
1323:
1298:
1294:
1249:
1243:
1198:
1194:
1154:
1150:
1091:Colon cancer
1037:
1007:keratinocyte
999:
989:CD4+ T cells
984:
976:
968:
932:
925:
875:
866:
858:
854:
850:
846:
842:
838:
834:
830:
826:
822:
821:)-HpETE, 12(
818:
814:
806:
802:
790:
786:
744:
706:Vasodilation
698:Prostacyclin
695:
680:
676:
672:
670:
665:
661:
657:
653:
649:
645:
641:
635:
625:
621:
617:
613:
599:
548:
488:
466:
462:
458:
447:
443:
439:
435:
431:
399:
393:
389:
385:
381:
379:
375:
371:
370:
78:Identifiers
68:
64:
60:
56:
4490:Fatty acids
4408:Precursors:
4231:Acebilustat
4105:inhibitors:
4075:Minocycline
3864:Zafirlukast
3809:Montelukast
3415:Leukotriene
3372:(Dinoprost)
3096:By function
3087:Virodhamine
2818:(Dinoprost)
2719:Prostanoids
2695:Eicosanoids
2631:(6): 1008.
1604:Eicosanoids
1011:db/db mouse
894:lymphocytes
878:bone marrow
825:)-HETE, 15(
817:)-HETE, 12(
772:-sensitive
718:neutrophils
616:)-hydroxy-5
434:)-hydroxy-5
400:12(S)-HHTrE
304:Properties
157:100.161.462
4383:Cilastatin
4320:Azelastine
4085:Timegadine
4057:Hyperforin
3988:inhibitors
3854:Tomelukast
3849:Tipelukast
3834:SKF-104353
3829:Ritolukast
3824:Pranlukast
3819:Pobilukast
3799:Masilukast
3784:ICI-198615
3774:Cinalukast
3583:Ticolubant
3553:Moxilubant
3528:CGS-25019C
3421:modulators
3280:leukocytes
3059:Nonclassic
1471:(1): 319.
1130:References
1044:metastasis
1000:High dose
886:eosinophil
882:neutrophil
871:lipoxin A4
782:eicosanoid
730:thrombosis
583:macrophage
534:paracrines
530:autocrines
480:Production
453:of its 12-
416:microsomes
339:Molar mass
170:IUPHAR/BPS
130:ChemSpider
106:3D model (
95:54397-84-1
85:CAS Number
4261:SC-57461A
4236:Captopril
4204:PD-146176
4161:Baicalein
4052:Fenleuton
4017:Baicalein
3958:Agonists:
3895:Agonists:
3859:Verlukast
3794:LY-170680
3789:Iralukast
3779:FPL-55712
3722:Agonists:
3678:ZK-158252
3673:LY-255283
3668:CP-195543
3619:Agonists:
3593:ZK-158252
3573:SB-209247
3548:LY-293111
3538:CP-195543
3533:CP-105696
3518:Amelubant
3500:LY-255283
3476:Agonists:
3418:signaling
3239:platelets
2995:Precursor
2901:Precursor
2737:Precursor
2702:Precursor
975:, and 15(
947:apoptotic
902:arthritis
890:mast cell
801:) and 15(
595:endotoxin
539:platelets
522:Platelets
508:(PGH2).
428:platelets
4484:Category
4456:See also
4352:Acivicin
4199:Luteolin
4118:BAYx1005
4090:Zileuton
4047:Curcumin
4042:CJ-13610
3932:BAYu9916
3927:BAYu9773
3844:Sulukast
3814:ONO-1078
3769:BAYx7195
3764:BAYu9916
3759:BAYu9773
3754:Ablukast
3642:15-HpETE
3632:12-HpETE
3578:SC-53228
3568:RP-69698
3563:RG-14893
3558:ONO-4057
3543:Etalocib
3429:Receptor
3282:: induce
3241:: induce
3067:Lipoxins
2655:24890114
2606:16978891
2571:24821912
2519:33252079
2511:24742066
2470:11433313
2462:23859232
2419:23603839
2375:22391335
2326:20090768
2244:33906245
2236:18042000
2201:19876785
2174:24313690
2139:24588652
2090:25480980
2040:11278893
1999:12895595
1959:10934230
1910:39982498
1861:18378794
1582:24009185
1485:23224081
1449:21068195
1356:10766802
1276:21081215
1097:See also
985:enhanced
981:knockout
956:cytokine
908:, etc.)
714:monocyte
579:monocyte
549:Various
526:thrombin
455:hydroxyl
4256:SA-6541
4027:BW-B70C
3869:ZD-3523
3839:SR-2640
3637:15-HETE
3622:12-HETE
3588:U-75302
3479:12-HETE
3435:ligands
3305:inhibit
3256:inhibit
2917:Initial
2646:4042644
2562:4042643
2427:5595069
2366:3389076
2285:7925341
2130:4128057
1950:2193217
1902:9576182
1852:2292216
1807:6808683
1799:3422086
1764:2281869
1728:8508808
1687:3107571
1651:3662534
1616:3272822
1573:3793602
1531:9785378
1493:9158244
1440:3033693
1400:2491846
1315:3124219
1235:4215079
1203:Bibcode
1173:4723909
1002:aspirin
973:12-HETE
602:ferrous
344:280.408
205:5283141
192:PubChem
139:4446265
4401:Others
4325:MK-886
4241:DG-051
4189:2-TEDC
4177:15-LOX
4151:2-TEDC
4139:12-LOX
4128:MK-886
4123:MK-591
4113:AM-679
4108:AM-103
4022:BW-A4C
4012:2-TEDC
3982:Enzyme
3804:MK-571
3627:12-HHT
3069:(LX) (
3011:Eoxins
2986:Eoxins
2756:Active
2653:
2643:
2604:
2569:
2559:
2517:
2509:
2468:
2460:
2425:
2417:
2373:
2363:
2324:
2283:
2242:
2234:
2199:
2172:
2137:
2127:
2088:
2038:
1997:
1957:
1947:
1908:
1900:
1859:
1849:
1805:
1797:
1762:
1726:
1685:
1649:
1614:
1580:
1570:
1529:
1491:
1483:
1447:
1437:
1398:
1354:
1313:
1274:
1264:
1233:
1226:433780
1223:
1171:
1034:Cancer
906:asthma
857:) or 6
606:ferric
593:(i.e.
575:CYP3A4
573:, and
571:CYP2S1
567:CYP2E1
563:CYP1B1
559:CYP1A2
555:CYP1A1
465:, and
418:(i.e.
376:12-HHT
288:SMILES
45:Names
4000:5-LOX
3943:CysLT
3880:CysLT
3707:CysLT
3693:CysLT
3351:labor
3331:fever
2945:SRS-A
2515:S2CID
2466:S2CID
2423:S2CID
2240:S2CID
1906:S2CID
1803:S2CID
1489:S2CID
935:HaCaT
833:),12(
776:from
708:(see
610:hemin
398:, or
253:InChI
108:JSmol
4099:FLAP
2988:(EX)
2894:(LT)
2860:(TX)
2730:(PG)
2651:PMID
2602:PMID
2567:PMID
2507:PMID
2458:PMID
2415:PMID
2371:PMID
2322:PMID
2281:PMID
2232:PMID
2197:PMID
2170:PMID
2135:PMID
2086:PMID
2036:PMID
1995:PMID
1955:PMID
1898:PMID
1857:PMID
1795:PMID
1760:PMID
1724:PMID
1683:PMID
1647:PMID
1612:PMID
1578:PMID
1527:PMID
1481:PMID
1445:PMID
1396:PMID
1352:PMID
1311:PMID
1272:PMID
1262:ISBN
1231:PMID
1169:PMID
1022:and
963:and
768:and
732:and
502:PGG2
492:and
180:6159
4368:LTD
4336:LTC
4304:LTC
4277:LTB
4215:LTA
4194:CDC
4166:CDC
4037:CDC
3604:BLT
3461:BLT
3447:BLT
3367:PGF
3358:PGE
3338:PGE
3318:PGE
3310:PGD
3295:LTB
3287:TXA
3269:PGI
3261:PGD
3246:TXA
3226:LTE
3218:LTD
3210:LTC
3202:PGI
3194:PGE
3177:TXB
3169:TXA
3161:PGF
3142:LTE
3134:LTD
3126:LTC
3118:TXA
3110:PGD
2763:D/J
2641:PMC
2633:doi
2629:211
2594:doi
2557:PMC
2549:doi
2545:211
2497:doi
2450:doi
2405:doi
2361:PMC
2353:doi
2312:doi
2308:130
2271:doi
2267:224
2224:doi
2162:doi
2125:PMC
2117:doi
2113:171
2076:doi
2072:157
2026:doi
2022:276
1987:doi
1945:PMC
1937:doi
1933:192
1888:doi
1884:101
1847:PMC
1839:doi
1835:205
1787:doi
1752:doi
1748:189
1714:doi
1710:214
1675:doi
1639:doi
1635:257
1568:PMC
1558:doi
1519:doi
1473:doi
1469:108
1435:PMC
1427:doi
1386:doi
1382:264
1342:doi
1338:275
1303:doi
1254:doi
1221:PMC
1211:doi
1159:doi
1155:248
849:,14
845:,10
797:of
785:12(
679:,10
648:,10
624:,10
589:or
520:.
442:,10
392:,10
380:12(
222:EPA
195:CID
67:,12
63:,10
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