259:
surrounds DNA (to partially balance the sum of the negative charges carried by each phosphate oxygen), thus forming a weak electrostatic association with the outer surface of DNA. From this position, the ligand diffuses along the surface of the DNA and may slide into the hydrophobic environment found between two base pairs that may transiently "open" to form an intercalation site, allowing the ethidium to move away from the hydrophilic (aqueous) environment surrounding the DNA and into the intercalation site. The base pairs transiently form such openings due to energy absorbed during collisions with solvent molecules.
730:
75:
102:
724:
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in 1961. One proposed mechanism of intercalation is as follows: In aqueous isotonic solution, the cationic intercalator is attracted electrostatically to the surface of the polyanionic DNA. The ligand displaces a sodium and/or magnesium cation present in the "condensation cloud" of such cations that
206:
found in aqueous solution) unwinds DNA by about 26°, whereas proflavine unwinds it by about 17°. This unwinding causes the base pairs to separate, or "rise", creating an opening of about 0.34 nm (3.4 Å). This unwinding induces local structural changes to the DNA strand, such as lengthening of
201:
In order for an intercalator to fit between base pairs, the DNA must dynamically open a space between its base pairs by unwinding. The degree of unwinding varies depending on the intercalator; for example, ethidium cation (the ionic form of
344:
Schatzschneider, Ulrich (2018). "Chapter 14. Metallointercalators and
Metalloinsertors: Structural Requirements for DNA Recognition and Anticancer Activity". In Sigel, Astrid; Sigel, Helmut; Freisinger, Eva; Sigel, Roland K. O. (eds.).
119:, electrostatically binding, or intercalating. Intercalation occurs when ligands of an appropriate size and chemical nature fit themselves in between base pairs of DNA. These ligands are mostly polycyclic,
254:
Intercalation as a mechanism of interaction between cationic, planar, polycyclic aromatic systems of the correct size (on the order of a base pair) was first proposed by
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155:
treatment to inhibit DNA replication in rapidly growing cancer cells. Examples include doxorubicin (adriamycin) and daunorubicin (both of which are used in treatment of
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1679:
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Intercalation induces structural distortions. Left: unchanged DNA strand. Right: DNA strand intercalated at three locations (black areas).
182:(II), because its complexes are very slow to decompose in the biological environment. Other metallic cations that have been used include
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207:
the DNA strand or twisting of the base pairs. These structural modifications can lead to functional changes, often to the inhibition of
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Metallointercalators are complexes of a metal cation with polycyclic aromatic ligands. The most commonly used metal ion is
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Luzzati, V.; Masson, F.; Lerman, L. S. (1961). "Interaction of DNA and proflavine: A small-angle x-ray scattering study".
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98:(DNA). This process is used as a method for analyzing DNA and it is also the basis of certain kinds of poisoning.
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Need to be chunked into sections, so that additional information can fit. Need to have dsRNA mention..
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2012:
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Proceedings of the
National Academy of Sciences of the United States of America
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304:"Synthetic metallomolecules as agents for the control of DNA structure"
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187:
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398:"Structural considerations in the interaction of DNA and acridines"
73:
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109:
There are several ways molecules (in this case, also known as
26:
105:
Ethidium intercalated between two adenine-thymine base pairs.
349:. Vol. 18. Berlin: de Gruyter GmbH. pp. 387–435.
215:
and DNA repair processes, which makes intercalators potent
347:
Metallo-Drugs: Development and Action of
Anticancer Agents
115:) can interact with DNA. Ligands may interact with DNA by
123:, and planar, and therefore often make good nucleic acid
190:(III). Typical ligands attached to the metal ion are
2347:
2298:
2078:
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2007:
1961:
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198:whose planar structure is ideal for intercalation.
219:. For this reason, DNA intercalators are often
127:. Intensively studied DNA intercalators include
973:
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8:
475:"The structure of the DNA-acridine complex"
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1685:
1445:
1160:
1143:
1021:
980:
966:
958:
751:
573:
550:
536:
528:
508:
498:
42:needs attention from an expert in Biology
942:Polyhedral skeletal electron pair theory
100:
294:
378:
368:
57:may be able to help recruit an expert.
302:Richards, A. D.; Rodgers, A. (2007).
7:
1249:ribonucleotide reductase inhibitors
1415:Ribonucleotide reductase inhibitor
1371:Ribonucleotide reductase inhibitor
284:Twisted intercalating nucleic acid
25:
1174:Dihydrofolate reductase inhibitor
734:
728:
722:
151:. DNA intercalators are used in
31:
1311:Thymidylate synthase inhibitor
1201:Thymidylate synthase inhibitor
1:
1231:Adenosine deaminase inhibitor
1072:Block microtubule disassembly
452:10.1016/S0022-2836(61)80026-0
417:10.1016/S0022-2836(61)80004-1
440:Journal of Molecular Biology
405:Journal of Molecular Biology
94:between the planar bases of
44:. The specific problem is:
2701:
640:Metal–ligand multiple bond
2635:
2521:Omacetaxine mepesuccinate
2411:Ciltacabtagene autoleucel
2401:Brexucabtagene autoleucel
720:
355:10.1515/9783110470734-020
274:Intercalation (chemistry)
2685:Supramolecular chemistry
2568:Talimogene laherparepvec
1435:Topoisomerase inhibitors
1354:DNA polymerase inhibitor
311:Chemical Society Reviews
2386:Axicabtagene ciloleucel
990:chemotherapeutic agents
227:(but not the endo) 8,9
2553:Sitimagene ceradenovec
2466:Idecabtagene vicleucel
2031:Methyl aminolevulinate
473:Lerman, L. S. (1963).
396:Lerman, L. S. (1961).
106:
79:
2042:Porphyrin derivatives
1738:Melphalan flufenamide
1385:Hypomethylating agent
994:antineoplastic agents
104:
96:deoxyribonucleic acid
77:
2371:Asparagine depleters
2300:Receptor antagonists
2214:+abiraterone acetate
630:Coordinate (dipolar)
500:10.1073/pnas.49.1.94
90:is the insertion of
2421:Denileukin diftitox
2321:Retinoid X receptor
2021:Aminolevulinic acid
1843:Triethylenemelamine
1675:Crosslinking of DNA
1406:Deoxyribonucleotide
1345:+gimeracil/oteracil
804:C–H···O interaction
586:Electron deficiency
491:1963PNAS...49...94L
55:WikiProject Biology
2662:Never to phase III
1479:Etirinotecan pegol
789:Resonance-assisted
279:Molecular tweezers
157:Hodgkin's lymphoma
117:covalently binding
107:
80:
2672:
2671:
2631:
2630:
2588:Tigilanol tiglate
2080:Enzyme inhibitors
2003:
2002:
1999:
1998:
1699:Nitrogen mustards
1669:
1668:
1429:
1428:
1131:
1130:
955:
954:
906:Electron counting
877:
876:
766:London dispersion
718:
717:
695:Metal aromaticity
72:
71:
18:DNA intercalation
16:(Redirected from
2692:
2593:Tisagenlecleucel
2365:Arsenic trioxide
2076:
2009:Photosensitizers
1800:Alkyl sulfonates
1714:Cyclophosphamide
1686:
1625:Anthracenediones
1446:
1420:Hydroxycarbamide
1161:
1144:
1022:
982:
975:
968:
959:
947:Jemmis mno rules
799:Dihydrogen bonds
752:
738:
732:
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660:Hyperconjugation
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323:10.1039/b609495c
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204:ethidium bromide
173:rhabdomyosarcoma
153:chemotherapeutic
133:ethidium bromide
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2047:Porfimer sodium
1995:
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1150:antimetabolites
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1147:DNA precursors/
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1137:DNA replication
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1037:Vinca alkaloids
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2201:PARP inhibitor
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988:Intracellular
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379:|journal=
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256:Leonard Lerman
236:
223:, such as the
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2496:Lurbinectedin
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2222:
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2215:
2212:
2209:
2207:
2203:
2202:
2198:
2195:
2191:
2190:
2186:
2183:
2179:
2178:
2174:
2171:
2167:
2166:
2162:
2158:
2155:
2153:
2150:
2148:
2145:
2143:
2140:
2139:
2138:
2137:
2133:
2130:
2127:
2125:
2122:
2120:
2117:
2115:
2112:
2110:
2106:
2105:
2102:
2098:
2095:
2091:
2090:
2086:
2085:
2083:
2081:
2077:
2074:
2070:
2063:
2060:
2058:
2055:
2053:
2050:
2048:
2044:
2043:
2039:
2037:
2034:
2032:
2029:
2027:
2024:
2022:
2019:
2018:
2016:
2014:
2010:
2006:
1991:
1988:
1986:
1983:
1981:
1978:
1976:
1972:
1969:
1968:
1966:
1964:
1963:Intercalation
1960:
1953:
1950:
1948:
1945:
1943:
1939:
1938:
1934:
1932:
1929:
1927:
1924:
1922:
1919:
1916:
1912:
1911:
1907:
1905:
1902:
1901:
1899:
1897:
1893:
1887:
1884:
1882:
1879:
1877:
1874:
1872:
1871:Dicycloplatin
1869:
1867:
1864:
1862:
1859:
1858:
1856:
1854:
1850:
1844:
1841:
1839:
1836:
1834:
1831:
1829:
1826:
1824:
1820:
1819:
1815:
1812:
1810:
1806:
1803:
1801:
1797:
1796:
1793:
1790:
1788:
1785:
1783:
1780:
1777:
1773:
1770:
1768:
1765:
1763:
1760:
1758:
1754:
1753:
1750:
1747:
1745:
1744:Prednimustine
1742:
1739:
1735:
1732:
1730:
1727:
1724:
1721:
1719:
1715:
1712:
1710:
1707:
1705:
1702:
1700:
1696:
1695:
1693:
1691:
1687:
1684:
1681:
1676:
1672:
1662:
1659:
1657:
1654:
1652:
1649:
1647:
1644:
1641:
1638:
1636:
1633:
1631:
1627:
1626:
1622:
1619:
1616:
1614:
1611:
1609:
1606:
1604:
1601:
1599:
1596:
1594:
1591:
1588:
1584:
1581:
1579:
1576:
1574:
1570:
1569:
1565:
1564:
1562:
1560:
1559:Intercalation
1556:
1552:
1545:
1542:
1540:
1536:
1535:
1531:
1530:
1528:
1526:
1522:
1515:
1512:
1510:
1507:
1505:
1502:
1500:
1497:
1495:
1492:
1490:
1487:
1485:
1482:
1480:
1477:
1475:
1472:
1470:
1467:
1465:
1461:
1460:
1456:
1455:
1453:
1451:
1447:
1444:
1441:
1436:
1432:
1421:
1417:
1416:
1412:
1411:
1409:
1407:
1403:
1396:
1393:
1391:
1387:
1386:
1382:
1381:
1377:
1373:
1372:
1368:
1367:
1363:
1362:+daunorubicin
1360:
1356:
1355:
1351:
1350:
1346:
1342:
1339:
1337:
1334:
1332:
1329:
1327:
1326:Doxifluridine
1324:
1322:
1319:
1317:
1313:
1312:
1308:
1307:
1305:
1303:
1299:
1292:
1289:
1287:
1283:
1282:
1278:
1276:
1275:Rabacfosadine
1273:
1271:
1268:
1265:
1262:
1260:
1257:
1255:
1251:
1250:
1246:
1242:
1241:
1237:
1233:
1232:
1228:
1227:
1225:
1223:
1219:
1212:
1209:
1207:
1203:
1202:
1198:
1195:
1192:
1190:
1187:
1185:
1182:
1180:
1176:
1175:
1171:
1170:
1168:
1166:
1162:
1159:
1156:
1151:
1145:
1142:
1138:
1134:
1123:
1119:
1118:
1114:
1111:
1108:
1106:
1103:
1101:
1098:
1096:
1093:
1091:
1088:
1086:
1082:
1081:
1077:
1076:
1074:
1070:
1063:
1060:
1058:
1055:
1053:
1050:
1048:
1045:
1043:
1039:
1038:
1034:
1033:
1031:
1028:
1023:
1020:
1017:
1012:
1008:
1004:
999:
995:
991:
983:
978:
976:
971:
969:
964:
963:
960:
948:
945:
943:
940:
936:
933:
931:
928:
926:
923:
921:
920:HĂĽckel's rule
918:
917:
916:
913:
912:
910:
907:
903:
897:
894:
892:
889:
888:
886:
884:
883:Bond cleavage
880:
870:
867:
865:
862:
860:
857:
855:
852:
850:
849:Intercalation
847:
844:
840:
839:Metallophilic
837:
835:
832:
830:
827:
825:
822:
821:
819:
815:
811:
805:
802:
800:
797:
795:
792:
790:
787:
785:
782:
781:
779:
777:
773:
767:
764:
763:
761:
759:
756:Van der Waals
753:
750:
746:
742:
737:
731:
725:
711:
710:
708:
706:
702:
696:
693:
692:
690:
688:
684:
676:
673:
671:
668:
667:
666:
663:
661:
658:
656:
653:
651:
648:
646:
643:
641:
638:
636:
633:
631:
628:
626:
623:
621:
618:
614:
611:
610:
609:
606:
602:
599:
597:
594:
592:
589:
588:
587:
584:
583:
581:
579:
575:
572:
568:
564:
560:
553:
548:
546:
541:
539:
534:
533:
530:
520:
516:
511:
506:
501:
496:
492:
488:
485:(1): 94–102.
484:
480:
476:
469:
466:
461:
457:
453:
449:
445:
441:
434:
431:
426:
422:
418:
414:
410:
406:
399:
392:
389:
384:
372:
364:
360:
356:
352:
348:
340:
337:
332:
328:
324:
320:
317:(3): 471–83.
316:
312:
305:
298:
295:
289:
285:
282:
280:
277:
275:
272:
270:
269:Anthracycline
267:
266:
262:
260:
257:
252:
250:
246:
242:
234:
230:
226:
222:
218:
214:
210:
209:transcription
205:
199:
197:
193:
189:
185:
181:
176:
174:
170:
166:
165:Wilm's tumour
162:
158:
154:
150:
146:
142:
138:
134:
130:
126:
122:
118:
114:
113:
103:
99:
97:
93:
89:
88:intercalation
85:
76:
66:
63:November 2023
56:
51:
47:
43:
40:This article
38:
29:
28:
19:
2573:Tazemetostat
2537:Alitretinoin
2530:
2456:Estramustine
2436:Elsamitrucin
2426:Eflornithine
2380:Pegaspargase
2376:Asparaginase
2369:
2338:Testolactone
2331:
2319:
2307:
2261:
2246:Panobinostat
2229:
2199:
2187:
2175:
2163:
2134:
2099:
2087:
2040:
2036:Padeliporfin
1975:Dactinomycin
1971:Streptomyces
1962:
1952:Temozolomide
1947:Mitozolomide
1935:
1926:Mitobronitol
1915:Procarbazine
1908:
1896:Nonclassical
1821:
1798:
1792:Streptozocin
1757:Nitrosoureas
1755:
1729:Chlorambucil
1723:Trofosfamide
1709:Chlormethine
1704:Bendamustine
1697:
1635:Mitoxantrone
1630:Losoxantrone
1623:
1583:Daunorubicin
1566:
1558:
1532:
1469:Camptothecin
1457:
1413:
1383:
1369:
1352:
1336:Fluorouracil
1316:Capecitabine
1309:
1279:
1243:
1229:
1199:
1194:Pralatrexate
1184:Methotrexate
1172:
1115:
1078:
1035:
925:Baird's rule
645:Charge-shift
608:Hypervalence
482:
478:
468:
446:(5): 634–9.
443:
439:
433:
411:(1): 18–30.
408:
404:
391:
346:
339:
314:
310:
297:
253:
221:carcinogenic
200:
177:
161:dactinomycin
110:
108:
87:
84:biochemistry
81:
60:
52:for details.
45:
41:
2648:from market
2618:Vorasidenib
2598:Trabectedin
2583:Tiazofurine
2578:Tebentafusp
2563:Tagraxofusp
2526:Plitidepsin
2501:Mitoguazone
2446:Epacadostat
2416:Demecolcine
2360:Aflibercept
2333:Sex steroid
2206:Fuzuloparib
2147:Carfilzomib
2119:Palbociclib
2109:Abemaciclib
2062:Verteporfin
2026:Efaproxiral
1942:Dacarbazine
1904:Altretamine
1886:Satraplatin
1881:Oxaliplatin
1861:Carboplatin
1838:Triaziquone
1809:Mannosulfan
1787:Ranimustine
1767:Fotemustine
1608:Pirarubicin
1593:Doxorubicin
1587:+cytarabine
1573:Aclarubicin
1534:Podophyllum
1459:Camptotheca
1390:Azacitidine
1376:Gemcitabine
1331:Floxuridine
1264:Fludarabine
1259:Clofarabine
1245:Halogenated
1236:Pentostatin
1211:Raltitrexed
1179:Aminopterin
1122:Ixabepilone
1117:Epothilones
1085:Cabazitaxel
1062:Vinorelbine
1047:Vincristine
1042:Vinblastine
1027:microtubule
915:Aromaticity
891:Heterolysis
869:Salt bridge
814:Noncovalent
784:Low-barrier
665:Aromaticity
655:Conjugation
635:Pi backbond
213:replication
196:terpyridine
149:thalidomide
145:doxorubicin
2613:Verdinexor
2608:Venetoclax
2516:Oblimersen
2511:Navitoclax
2491:Lucanthone
2486:Lonidamine
2481:Lifileucel
2476:Ivosidenib
2471:Imetelstat
2441:Enasidenib
2431:Elesclomol
2396:Bexarotene
2391:Belzutifan
2326:Bexarotene
2314:Atrasentan
2289:Umbralisib
2284:Idelalisib
2274:Copanlisib
2256:Vorinostat
2251:Romidepsin
2241:Entinostat
2236:Belinostat
2194:Masoprocol
2182:Tiazofurin
2170:Anagrelide
2142:Bortezomib
2129:Seliciclib
2124:Ribociclib
2104:inhibitors
2094:Tipifarnib
2057:Temoporfin
2052:Talaporfin
1990:Plicamycin
1985:Mitomycins
1931:Pipobroman
1910:Hydrazines
1876:Nedaplatin
1828:Carboquone
1823:Aziridines
1814:Treosulfan
1762:Carmustine
1749:Uramustine
1718:Ifosfamide
1690:Alkylating
1651:Bisantrene
1640:Pixantrone
1613:Valrubicin
1603:Idarubicin
1598:Epirubicin
1544:Teniposide
1499:Lurtotecan
1494:Irinotecan
1395:Decitabine
1359:Cytarabine
1302:Pyrimidine
1291:Tioguanine
1281:Thiopurine
1270:Nelarabine
1254:Cladribine
1206:Pemetrexed
1189:Pemetrexed
1165:Folic acid
1105:Paclitaxel
1057:Vinflunine
843:aurophilic
824:Mechanical
290:References
249:quinacrine
245:proflavine
192:dipyridine
186:(III) and
141:daunomycin
137:proflavine
2658:Phase III
2646:Withdrawn
2623:Vosaroxin
2603:Veliparib
2558:Sotorasib
2548:Selinexor
2542:Tretinoin
2532:Retinoids
2461:Glasdegib
2406:Celecoxib
2355:Adagrasib
2279:Duvelisib
2269:Alpelisib
2224:Rucaparib
2211:Niraparib
2152:Oprozomib
2114:Alvocidib
1980:Bleomycin
1937:Triazenes
1921:Etoglucid
1866:Cisplatin
1782:Nimustine
1776:Semustine
1772:Lomustine
1734:Melphalan
1661:Menogaril
1656:Crisnatol
1646:Amsacrine
1618:Zorubicin
1578:Amrubicin
1539:Etoposide
1514:Topotecan
1509:Silatecan
1504:Rubitecan
1489:Gimatecan
1474:Cositecan
1464:Belotecan
1140:inhibitor
1110:Tesetaxel
1100:Ortataxel
1095:Larotaxel
1090:Docetaxel
1052:Vindesine
935:spherical
896:Homolysis
859:Cation–pi
834:Chalcogen
794:Symmetric
650:Hapticity
381:ignored (
371:cite book
241:acridines
233:aflatoxin
180:ruthenium
163:(used in
129:berberine
92:molecules
50:talk page
2679:Category
2506:Mitotane
2451:Eribulin
2219:Olaparib
2157:Ixazomib
1833:Thiotepa
1805:Busulfan
1484:Exatecan
1321:Carmofur
1029:assembly
992: /
864:Anion–pi
854:Stacking
776:Hydrogen
687:Metallic
578:Covalent
570:(strong)
519:13929834
460:14467543
425:13761054
363:29394033
331:17325786
263:See also
243:such as
217:mutagens
121:aromatic
48:See the
1440:S phase
1341:Tegafur
1155:S phase
1080:Taxanes
1016:M phase
829:Halogen
675:bicyclo
620:Agostic
487:Bibcode
229:epoxide
188:iridium
184:rhodium
159:), and
112:ligands
2641:WHO-EM
2265:(Pi3K)
1222:Purine
1025:Block
930:Möbius
758:forces
748:(weak)
517:
510:300634
507:
458:
423:
361:
329:
147:, and
125:stains
2177:IMPDI
2072:Other
908:rules
817:other
705:Ionic
613:3c–4e
601:8c–2e
596:4c–2e
591:3c–2e
401:(PDF)
307:(PDF)
2263:PIKI
2231:HDAC
1680:CCNS
670:homo
625:Bent
515:PMID
456:PMID
421:PMID
383:help
359:PMID
327:PMID
239:and
211:and
194:and
2309:ERA
2165:PhI
2136:PrI
2101:CDK
2013:PDT
1011:MIs
1007:SPs
998:L01
505:PMC
495:doi
448:doi
413:doi
351:doi
319:doi
247:or
231:of
225:exo
175:).
82:In
2681::
2654::
2189:LI
2089:FI
1555:II
1525:II
1347:))
513:.
503:.
493:.
483:49
481:.
477:.
454:.
442:.
419:.
407:.
403:.
375::
373:}}
369:{{
357:.
325:.
315:36
313:.
309:.
251:.
171:,
167:,
143:,
139:,
135:,
131:,
86:,
2544:)
2535:(
2382:)
2378:/
2374:(
2340:)
2336:(
2328:)
2324:(
2316:)
2312:(
2291:)
2267:(
2258:)
2234:(
2226:)
2204:(
2196:)
2192:(
2184:)
2180:(
2172:)
2168:(
2131:)
2107:(
2096:)
2092:(
2064:)
2045:(
2011:/
1992:)
1973:(
1954:)
1940:(
1917:)
1913:(
1825::
1816:)
1807:(
1802::
1778:)
1774:(
1759::
1740:)
1736:(
1725:)
1716:(
1701::
1682:)
1678:(
1642:)
1628:(
1620:)
1589:)
1585:(
1571:(
1557:+
1546:)
1537:(
1516:)
1462:(
1450:I
1442:)
1438:(
1422:)
1418:(
1397:)
1388:(
1378:)
1374:(
1364:)
1357:(
1343:(
1314:(
1293:)
1284:(
1266:)
1252:(
1247:/
1238:)
1234:(
1213:)
1204:(
1196:)
1177:(
1157:)
1153:(
1124:)
1120:(
1112:)
1083:(
1064:)
1040:(
1018:)
1014:(
1009:/
1000:)
996:(
981:e
974:t
967:v
845:)
841:(
551:e
544:t
537:v
521:.
497::
489::
462:.
450::
444:3
427:.
415::
409:3
385:)
365:.
353::
333:.
321::
237:1
235:B
65:)
61:(
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
