25:
17:
539:
163:). Seemingly, the high activity of CYP1A1 in the intestinal mucosa prevents major amounts of ingested benzopyrene from entering portal blood and systemic circulation. The intestinal (but not hepatic) detoxification mechanism seems to depend on receptors that recognize bacterial surface components (
302:
Uno, S.; Dalton, TP; Dragin, N; Curran, CP; Derkenne, S; Miller, ML; Shertzer, HG; Gonzalez, FJ; Nebert, DW (2006). "Oral
Benzopyrene in Cyp1 knockout mouse lines: CYP1A1 important in detoxication, CYP1B1 metabolism required for immune damage independent of total-body burden and clearance rate".
159:
and carcinogens. The mechanism of action of benzopyrene-related DNA modification has been investigated extensively and relates to the activity of cytochrome P450 subclass 1A1 (
144:
456:
Denissenko, M. F.; Pao, A.; Tang, M.-s.; Pfeifer, G. P. (1996). "Preferential
Formation of Benzopyrene Adducts at Lung Cancer Mutational Hotspots in P53".
996:
508:
160:
352:
579:
69:
570:
136:. Fumes that develop from fat dripping on blistering charcoal are rich in benzopyrene, which can condense on grilled goods.
986:
148:
250:
W. D. Betts "Tar and Pitch" in Kirk‑Othmer
Encyclopedia of Chemical Technology, 1997, John Wiley & Sons, New York.
888:
48:. Structurally speaking, the colorless isomers of benzopyrene are pentacyclic hydrocarbons and are fusion products of
348:"Basal and Inducible CYP1 mRNA Quantitation and Protein Localization throughout the Mouse Gastrointestinal Tract"
267:
Larsson, B. K.; Sahlberg, GP; Eriksson, AT; Busk, LA (1983). "Polycyclic aromatic hydrocarbons in grilled food".
721:
152:
543:
782:
777:
81:
991:
767:
762:
757:
752:
675:
465:
410:
194:
93:
705:
89:
823:
563:
489:
328:
884:
660:
481:
438:
379:
320:
284:
874:
670:
665:
473:
428:
418:
369:
361:
312:
276:
251:
37:
346:
Uno, S.; Dragin, N.; Miller, M. L.; Dalton, T. P.; Gonzalez, F. J.; Nebert, D. W. (2008).
255:
129:
469:
414:
365:
924:
919:
833:
802:
736:
731:
624:
433:
398:
397:
Do, KN; Fink, LN; Jensen, TE; Gautier, L; Parlesak, A (2012). Lebedeva, Irina V (ed.).
374:
347:
231:
226:
210:
85:
65:
61:
509:"Need to Track Organic Nano-Particles Across the Universe? NASA's Got an App for That"
980:
556:
97:
332:
185:
for tracking polycyclic aromatic hydrocarbons (PAHs), including benzopyrene, in the
869:
818:
700:
685:
644:
619:
548:
493:
109:
477:
423:
843:
828:
603:
198:
171:
117:
101:
772:
741:
629:
214:
156:
140:
965:
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950:
879:
787:
695:
639:
53:
24:
16:
442:
383:
324:
316:
538:
485:
288:
960:
914:
904:
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864:
848:
838:
792:
680:
634:
593:
206:
186:
125:
113:
280:
929:
909:
899:
598:
121:
139:
Benzopyrenes are harmful because they form carcinogenic and mutagenic
797:
690:
190:
133:
105:
57:
49:
945:
209:, are widespread throughout the universe, and are associated with
182:
23:
15:
513:
205:. PAHs seem to have been formed several billion years after the
202:
178:
164:
552:
399:"TLR2 controls intestinal carcinogen detoxication by CYP1A1"
170:
Evidence exists to link benzopyrene to the formation of
193:
in the universe may be associated with PAHs, possible
938:
857:
811:
714:
653:
612:
586:
100:and occurs together with other related pentacyclic
189:. According to scientists, more than 20% of the
564:
8:
145:(+)-benzopyrene-7,8-dihydrodiol-9,10-epoxide
571:
557:
549:
432:
422:
373:
243:
68:. They belong to the chemical class of
132:, wood smoke, and burnt foods such as
256:10.1002/0471238961.20011802052020.a01
7:
507:Hoover, Rachel (February 21, 2014).
366:10.1016/j.freeradbiomed.2007.10.044
14:
353:Free Radical Biology and Medicine
28:Chemical structure of benzopyrene
20:Chemical structure of benzopyrene
997:Polycyclic aromatic hydrocarbons
580:Polycyclic aromatic hydrocarbons
537:
96:. Benzopyrene is a component of
70:polycyclic aromatic hydrocarbons
1:
116:. It is naturally emitted by
478:10.1126/science.274.5286.430
424:10.1371/journal.pone.0032309
151:into DNA, interfering with
60:species of benzopyrene are
1013:
80:Related compounds include
183:greatly upgraded database
124:and can also be found in
746:-Benzopyrene(Olympicene)
147:from benzopyrene) which
155:. They are considered
317:10.1124/mol.105.021501
29:
21:
722:Benzacephenanthrylene
546:at Wikimedia Commons
27:
19:
987:Endocrine disruptors
64:and the less common
706:Tricyclobutabenzene
470:1996Sci...274..430D
415:2012PLoSO...732309D
281:10.1021/jf00118a049
195:starting materials
177:In February 2014,
122:volcanic eruptions
40:with the formula C
30:
22:
974:
973:
885:Hexabenzocoronene
768:Benzofluoranthene
763:Benzofluoranthene
758:Benzofluoranthene
753:Benzofluoranthene
676:Benzophenanthrene
542:Media related to
269:J Agric Food Chem
82:cyclopentapyrenes
1004:
875:Diindenoperylene
783:Dibenzanthracene
778:Dibenzanthracene
773:trans-Bicalicene
573:
566:
559:
550:
541:
526:
525:
523:
521:
504:
498:
497:
453:
447:
446:
436:
426:
394:
388:
387:
377:
343:
337:
336:
311:(4): 1103–1112.
299:
293:
292:
264:
258:
248:
104:species such as
38:organic compound
1012:
1011:
1007:
1006:
1005:
1003:
1002:
1001:
977:
976:
975:
970:
939:General classes
934:
853:
807:
710:
649:
608:
582:
577:
535:
530:
529:
519:
517:
506:
505:
501:
464:(5286): 430–2.
455:
454:
450:
396:
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391:
345:
344:
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301:
300:
296:
266:
265:
261:
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130:cigarette smoke
78:
54:phenylene group
47:
43:
12:
11:
5:
1010:
1008:
1000:
999:
994:
989:
979:
978:
972:
971:
969:
968:
963:
958:
953:
948:
942:
940:
936:
935:
933:
932:
927:
925:Trinaphthylene
922:
920:Superphenalene
917:
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907:
902:
897:
892:
882:
877:
872:
867:
861:
859:
855:
854:
852:
851:
846:
841:
836:
834:Dibenzopyrenes
831:
826:
821:
815:
813:
809:
808:
806:
805:
803:Tetraphenylene
800:
795:
790:
785:
780:
775:
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750:
749:
748:
739:
734:
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718:
716:
712:
711:
709:
708:
703:
698:
693:
688:
683:
678:
673:
668:
663:
661:Benzanthracene
657:
655:
651:
650:
648:
647:
642:
637:
632:
627:
625:Acenaphthylene
622:
616:
614:
610:
609:
607:
606:
601:
596:
590:
588:
584:
583:
578:
576:
575:
568:
561:
553:
534:
533:External links
531:
528:
527:
499:
448:
389:
360:(4): 570–583.
338:
305:Mol. Pharmacol
294:
275:(4): 867–873.
259:
242:
241:
239:
236:
235:
234:
229:
222:
219:
94:naphthopyrenes
86:dibenzopyrenes
77:
74:
45:
41:
13:
10:
9:
6:
4:
3:
2:
1009:
998:
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993:
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967:
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944:
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941:
937:
931:
928:
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908:
906:
903:
901:
898:
896:
893:
890:
886:
883:
881:
878:
876:
873:
871:
868:
866:
863:
862:
860:
856:
850:
847:
845:
842:
840:
837:
835:
832:
830:
827:
825:
824:Benzoperylene
822:
820:
817:
816:
814:
810:
804:
801:
799:
796:
794:
791:
789:
786:
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723:
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719:
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713:
707:
704:
702:
699:
697:
694:
692:
689:
687:
684:
682:
679:
677:
674:
672:
671:Benzofluorene
669:
667:
666:Benzofluorene
664:
662:
659:
658:
656:
652:
646:
643:
641:
638:
636:
633:
631:
628:
626:
623:
621:
618:
617:
615:
611:
605:
602:
600:
597:
595:
592:
591:
589:
585:
581:
574:
569:
567:
562:
560:
555:
554:
551:
547:
545:
540:
532:
516:
515:
510:
503:
500:
495:
491:
487:
483:
479:
475:
471:
467:
463:
459:
452:
449:
444:
440:
435:
430:
425:
420:
416:
412:
409:(3): e32309.
408:
404:
400:
393:
390:
385:
381:
376:
371:
367:
363:
359:
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354:
349:
342:
339:
334:
330:
326:
322:
318:
314:
310:
306:
298:
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286:
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278:
274:
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263:
260:
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158:
154:
153:transcription
150:
146:
142:
137:
135:
131:
127:
123:
119:
115:
111:
110:fluoranthenes
107:
103:
99:
95:
91:
90:indenopyrenes
87:
83:
75:
73:
71:
67:
63:
59:
55:
51:
39:
35:
26:
18:
870:Dicoronylene
819:Anthanthrene
743:
726:
701:Triphenylene
686:Fluoranthene
645:Phenanthrene
620:Acenaphthene
544:Benzopyrenes
536:
520:February 22,
518:. Retrieved
512:
502:
461:
457:
451:
406:
402:
392:
357:
351:
341:
308:
304:
297:
272:
268:
262:
246:
181:announced a
176:
169:
138:
118:forest fires
79:
33:
31:
992:Carcinogens
844:Triangulene
829:Corannulene
737:Benzopyrene
732:Benzopyrene
727:Benzopyrene
604:Naphthalene
232:Benzopyrene
227:Benzopyrene
172:lung cancer
149:intercalate
141:metabolites
66:benzopyrene
62:benzopyrene
34:benzopyrene
981:Categories
889:Hexa-cata-
630:Anthracene
238:References
215:exoplanets
157:pollutants
966:Phenacene
956:Cyclacene
951:Circulene
880:Heptacene
788:Pentacene
696:Tetracene
640:Phenalene
211:new stars
199:formation
143:(such as
961:Helicene
915:Sumanene
905:Rubicene
895:Kekulene
865:Coronene
858:7+ rings
849:Zethrene
839:Hexacene
793:Perylene
681:Chrysene
635:Fluorene
594:Butalene
443:22442665
403:PLOS ONE
384:17997381
333:10834208
325:16377763
221:See also
207:Big Bang
197:for the
187:universe
126:coal tar
114:perylene
102:aromatic
76:Overview
58:isomeric
930:Truxene
910:Rubrene
900:Ovalene
812:6 rings
715:5 rings
654:4 rings
613:3 rings
599:Azulene
587:2 rings
494:3589066
486:8832894
466:Bibcode
458:Science
434:3307708
411:Bibcode
375:2754765
289:6352775
108:, benzo
798:Picene
691:Pyrene
492:
484:
441:
431:
382:
372:
331:
323:
287:
191:carbon
161:CYP1A1
134:coffee
112:, and
106:picene
56:. Two
52:and a
50:pyrene
36:is an
946:Acene
490:S2CID
329:S2CID
98:pitch
522:2014
514:NASA
482:PMID
439:PMID
380:PMID
321:PMID
285:PMID
213:and
203:life
179:NASA
165:TLR2
120:and
92:and
474:doi
462:274
429:PMC
419:doi
370:PMC
362:doi
313:doi
277:doi
252:doi
201:of
167:).
983::
511:.
488:.
480:.
472:.
460:.
437:.
427:.
417:.
405:.
401:.
378:.
368:.
358:44
356:.
350:.
327:.
319:.
309:69
307:.
283:.
273:31
271:.
217:.
174:.
128:,
88:,
84:,
72:.
46:12
42:20
32:A
891:)
887:(
744:H
742:6
572:e
565:t
558:v
524:.
496:.
476::
468::
445:.
421::
413::
407:7
386:.
364::
335:.
315::
291:.
279::
254::
44:H
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
