1091:
mutation. When the amount of benzofluorene is increased in TA 100 yeast strain, the amount of revertants per plate does not increase. Only in the TA98 strain plate, which contained a fraction of a rat liver, a higher dose of benzofluorene seems to correspond with a larger amount of revertants. This indicates that benzofluorene is metabolized by enzymes in the rat liver into more potent mutagenic compounds. These compounds only affected the TA98 strain. This indicates that the adducts formed by benzofluorene metabolites cause
279:
166:
465:
51:
575:
531:
42:
1073:. The results of this are presented as BaPeq, which equals the concentration of the compound, times the potency of the compound compared to benzopyrene (RPF). Although the concentrations measured of benzofluorene are quite low, when corrected for mutagenicity, benzofluorene is the most important PAH of those that were measured in terms of possible health risks.
647:. There is also evidence that a larger number of metabolites are formed in the lungs, which might explain why benzofluorene is such a potent lung tumorigen. It is possible that benzofluorene may have a unique (and still unknown) mechanism of activation or transportation, which explains why the lungs are targeted. The initial steps of the metabolism, the
372:
710:. The formation of DNA adducts in human breast tumors, hepatoma and colon adenocarcinoma by these metabolites has been shown in vitro. These adducts and the ones that were observed in lung tumors of mice were similar, which strengthens the hypothesis that human cells are capable of forming the mutagenic metabolites.
678:. Glutathione conjugates are further metabolized to mercapturic acids in the kidney and are excreted in the urine. The hydroxylated metabolites of the PAHs are excreted in human urine both as free hydroxylated metabolites and as hydroxylated metabolites conjugated to glucuronic acid and sulfate.
455:
ring. This benzene ring is attached to carbon 3 and 4 of the fluorene-derived molecule. The 3D structure of benzofluorene is depicted in the infobox on the right as well. It is mostly flat, because it consists of 3 aromatic rings. Only the 2 hydrogen atoms on the 5 ring are oriented into the 3D
1090:
was performed on benzofluorene. Two different strains were used, TA100 and TA98. One group of each strain had a rat liver fraction and one group did not. The difference between the TA100 and the TA98 strain is that the TA98 strain has a frameshift mutation, and the TA100 has a base substitution
1165:
The effects of exposure to benzofluorene were also researched on rats. In one of these studies the liver was established to be the main place of disposition of benzofluorene after a single oral dose regardless of the size of the dose. It was found that 55-69% of the labelled benzofluorene was
551:
ring in the bay or fjord region. These diol epoxide metabolites are reactive and capable of forming DNA adducts (see the adjacent image). While benzofluorene does not have a bay or fjord region it does undergo a similar transformation with a pseudo-bay region that reacts instead. The type of
737:
disruptors. To estimate the health effects that arise from exposure to PAHs and benzofluorene it is necessary to determine the concentration of these compounds in the atmosphere. This was done in a study by
Morisaki et al. 2016. They compared the concentrations of different PAHs including
1351:
698:
will occur during cell replication. In addition, it is known that the cells affected most appear to be those with rapid replication, such as bone marrow, skin, and lung tissue, whereas tissues with slower turnover rate like the liver are less susceptible.
1142:
developed lung tumors. DNA adducts in these mice were analyzed and could be traced back to benzofluorene. This and another similar study suggest a contribution of benzofluorene to the carcinogenic potency of coal tar when administered orally.
730:, crude oil or coal products are at highest risk for PAH exposure. In general, the PAHs are formed during these industrial processes by incomplete combustion or pyrolysis of organic matter. The higher the temperature the more PAHs are formed.
686:
The carcinogenic metabolites of benzofluorene bind to DNA which involves the opening of the epoxide ring in benzofluorene anti- and syn-diolepoxide. The benzofluorene metabolites bind in a yet unknown fashion to the DNA.
611:(transport medium) in which the PAHs are located, the percentages of absorption can differ. Ingestion of benzofluorene makes it a very potent lung tumorigen In particular, benzofluorene is better absorbed in the lungs.
1404:
Kazlauskas K, Kreiza G, Radiunas E, Adomenas P, Adomeniene O, Karpavicius K, Bucevicius J, Jankauskas V, Jursenas S (2015). "Concentration effects on spontaneous and amplified emission in benzofluorenes".
1157:
This figure shows the DNA adduct level after a certain dose of benzofluorene was applied to the skin of mice. This level is similar in the lungs and in the skin implying that benzofluorene is a systemic
718:
Benzofluorene belongs to a group of compounds called polycyclic aromatic hydrocarbons (PAHs). PAHs and their derivatives are ubiquitous in the environment and they are produced in several industrial and
706:
application in mice with coal tar, but also when it is ingested. Next to its involvement in lung tumors, benzofluorene and its metabolites are expected to be involved in the formation of different
1170:
while 8–10% was found to be eliminated via urine. While the benzofluorene found in the feces was not biotransformed, the urine samples mainly showed polar metabolites of benzofluorene.
28:
385:
1858:
Koganti A, Singh R, Ma BL, Weyand EH (2001). "Comparative analysis of PAH:DNA adducts formed in lung of mice exposed to neat coal tar and soils contaminated with coal tar".
690:
When a DNA adduct forms at a site critical to the regulation of cell differentiation or growth it can cause cancer. If an aberration in the DNA is not well repaired by the
473:
488:
Benzofluorene occurs naturally in tar, but can also be manually synthesized in a four step process, which is depicted in the picture below. The starting product is
1107:
1949:
1114:
670:. More research on this topic is necessary for benzofluorene. Glucuronide and sulfate conjugates of PAH metabolites are generally excreted in the
1745:"U.S. EPA. Development of a Relative Potency Factor (RPF) Approach for Polycyclic Aromatic Hydrocarbon (PAH) Mixtures (External Review Draft)"
1577:
Librando V, Sarpietro MG, Castelli F (2003). "Role of lipophilic medium in the absorption of polycyclic aromatic compounds by biomembranes".
1499:
Weyand EH, Parimoo B, Reuhl KR, Goldstein LS, Wang JQ, Harvey RG (2004). "7H-Benzo[C]Fluorene: A Potent
Systemic Lung Carcinogen".
619:
Once it is absorbed, benzofluorene enters the lymph, circulates in the blood and is metabolized. The distribution of PAHs depends on their
560:
702:
Exposure to benzofluorene in vivo leads to the induction of mainly lung tumors where it acts as a DNA adductor. Lung tumors arise after
559:
is depicted in the image below. First benzofluorene (1) is transformed into trans-3,4-dihydrodiol (2). This substance is transformed by
1534:
Seto H, Ohkubo T, Kanoh T, Koike M, Nakamura K, Kawahara Y (1993). "Determination of polycyclic aromatic hydrocarbons in the lung".
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481:
408:
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1954:
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Concentrations of benzofluorene and some other PAHs in air in
Beijing and Kanazawa and the relative potency of these PAHs.
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Cizmas L; Zhou G-d; Safe SH; McDonald TJ; Zhu L; Donnelly KC (2004). "Comparative in vitro and in vivo genotoxicities of 7
392:
236:
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it is a group 3 carcinogen (not classifiable as to its carcinogenicity to humans). Other names for benzofluorene are 7
257:
691:
173:
727:
1773:
Lavoie EJ, Tulley L, Bedenko V, Hoffmann D (1981). "Mutagenicity of methylated fluorenes and benzofluorenes".
1666:]fluorene in Urban Air: HPLC Determination and Mutagenic Contribution Relative to Benzo[a]pyrene"
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in general are mostly absorbed via ingestion, inhalation, and dermal contact. Also, depending on the
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41:
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Koganti A, Singh R, Rozett K, Modi N, Goldstein LS, Roy TA, Zhang FJ, Harvey RG, Weyand EH (2000).
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Some of these PAHs, such as benzofluorene, are carcinogens and mutagens and act as possible
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Wang JQ, Weyand EH, Harvey RG (2002). "Synthesis of suspected carcinogenic metabolites of 7
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The structure of benzofluorene is depicted in the infobox on the right. It is an aromatic
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Dose response curve of benzofluorene was applied to the skin of mice. Data derived from
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123:
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1614:"7H-Benzo[c]fluorene DNA adduct formation in different human cells in culture"
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Goth-Goldstein, Regine; Marion L. Russell; Bhama
Parimoo & Eric H. Weyand (2002).
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properties. The mutagenicity of benzofluorene is mainly attributed to formation of
627:, because of this lipophilicity. This has been proven for similar substances like
1922:
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Another study found that benzofluorene is also carcinogenic in mice when applied
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The researchers corrected for the relative mutagenicity of compounds compared to
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1262:-benzofluorene, a coal tar component implicated in causation of lung tumors".
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1815:-benzofluorene, manufactured gas plant residue (MGP), and MGP fractions".
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416:
419:, cigarette smoke and smog and thought to be a major contributor to its
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Except where otherwise noted, data are given for materials in their
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Chopard-Lallier M, Perdu E, Jamin E, Brochot C, Craved J (2014).
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Agency for Toxic
Substances and Disease Registry (ATSDR) (2009).
1214:]fluorene: a major DNA adduct-forming component of coal tar"
1150:, inducing lung and skin cancer. Of the results of this study a
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543:
In general PAH carcinogenesis involves activation by the enzyme
432:
424:
191:
654:
For many PAHs it has been proven that they are conjugated, in
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Benzofluorene is mainly metabolized by the CYP enzymes in the
515:. Benzofluorenone-9 (4) is generated by self-condensation of 2
1660:
Morisaki H, Nakamura S, Tang N, Toriba A, Hayakawa K (2016).
738:
benzofluorene in
Beijing and Kanazawa in winter and summer.
346:
125–127 °C (257–261 °F; 398–400 K) predicted
262:
1253:
1251:
1249:
1806:
1804:
1366:. Toronto Research Chemicals Toronto Research Chemicals
380:
1453:"Toxicity of Polycyclic Aromatic Hydrocarbons (PAH)"
635:, but has yet to be investigated for benzofluorene.
726:Workers in industries or trades using or producing
552:cytochrome P 450 involved is thought to be CYP1A1.
439:-benzofluorene, 3,4-benzofluorene, and NSC 89264.
1494:
1492:
1490:
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1444:
623:and probably benzofluorene can easily cross the
356:398 °C (748 °F; 671 K) predicted
224:
1768:
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102:
81:Tetracycloheptadeca-1,3,5,7,9,12,14,16-octaene
519:-inden-1-one, when heated. The final step is
8:
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507:. This substance is dehydrobrominated to 2
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1579:Environmental Toxicology and Pharmacology
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583:ADME of benzofluorene and PAHs in general
563:into the highly carcinogenic metabolites
500:to 3-bromoindanone (2) using the reagent
427:that are reactive and capable of forming
244:
1138:In one animal study, mice that were fed
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740:
1817:Environmental and Molecular Mutagenesis
1716:"BaP and PAH from coal-derived sources"
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273:
1751:. U.S. Environmental Protection Agency
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1127:of benzofluorene. Data derived from
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19:The correct title of this article is
7:
1154:has been made, see the image above.
547:to diol epoxide metabolites with an
1725:. Health Council of the Netherlands
1407:Physical Chemistry Chemical Physics
511:-inden-1-one (3) using the reagent
215:
199:
587:fluorene and PAHs in general": -->
14:
1950:Polycyclic aromatic hydrocarbons
1112:
1105:
527:, generating benzofluorene (5).
451:-derived molecule with an extra
370:
308:
49:
40:
415:activity. It is a component of
409:polycyclic aromatic hydrocarbon
366:(at 25 °C , 100 kPa).
472:(at center), in this case the
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1:
1591:10.1016/s1382-6689(03)00007-3
1501:Polycyclic Aromatic Compounds
1298:"7H-Benzo[c]fluorene"
1923:10.1016/j.toxlet.2014.06.838
1787:10.1016/0165-7992(81)90027-0
1327:]fluorene on Chemspider"
1536:Arch Environ Contam Toxicol
578:Metabolism of benzofluorene
1971:
1903:"Disposition of benzo[
534:Synthesis of benzofluorene
23:. The substitution of any
18:
1513:10.1080/10406630490426942
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1231:10.1093/carcin/21.8.1601
639:Metabolism and excretion
443:Structure and reactivity
651:, are described above.
1907:]fluorene in rats"
1683:10.2116/analsci.32.233
1636:Cite journal requires
1475:Cite journal requires
714:Environmental exposure
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523:of this compound with
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29:technical restrictions
1955:Tetracyclic compounds
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567:-diolepoxide (3) and
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498:substitution reaction
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1917:(supplement): 4141.
1093:frameshift mutations
64:Preferred IUPAC name
1872:2001EnST...35.2704K
1860:Environ Sci Technol
1419:2015PCCP...1712935K
1413:(19): 12935–12948.
1152:dose-response curve
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682:Mechanism of action
431:. According to the
326: g·mol
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1911:Toxicology Letters
1723:gezondheidsraad.nl
1548:10.1007/bf01146169
1427:10.1039/C5CP01325A
1391:2008-09-22 at the
1134:Effects on animals
1086:In one study, the
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603:Benzofluorene and
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571:-diolepoxide (4).
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393:Infobox references
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1880:10.1021/es001532i
1866:(13): 2704–2709.
1276:10.1021/jo011149b
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1166:excreted via the
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525:hydrazine hydrate
505:-bromosuccinimide
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1360:]fluorene"
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1180:Benzofluorene
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405:Benzofluorene
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21:Benzofluorene
1926:. Retrieved
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1753:. Retrieved
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1027:360000±23000
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615:Distribution
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421:carcinogenic
404:
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87:Identifiers
79:Other names
69:
20:
1662:"Benzo[
1507:(1): 1–20.
1356:-Benzo[
1323:"Benzo[
1210:-benzo[
1071:benzopyrene
893:27000±20000
841:46000±28000
723:processes.
668:glutathione
660:glucuronide
478:benzopyrene
429:DNA adducts
425:metabolites
411:(PAH) with
336:1.185 g/cm
290:Properties
162:100.005.372
124:CHEBI:82403
1944:Categories
1693:2297/46773
1331:Chemspider
1264:J Org Chem
1186:References
1095:, and not
945:11000±6100
721:combustion
599:Absorption
539:Metabolism
494:brominated
490:1-indanone
480:, another
474:metabolite
470:DNA adduct
319:Molar mass
246:PX3702DW3A
135:ChemSpider
94:CAS Number
27:is due to
1775:Mutat Res
1148:topically
1125:Ames test
1088:Ames test
1037:8500±2100
735:endocrine
521:reduction
460:Synthesis
413:mutagenic
183:205-908-2
175:EC Number
1888:11452595
1837:15065203
1702:26860571
1670:Anal Sci
1619:10 March
1599:21782659
1564:21678586
1521:85148344
1458:10 March
1435:25912324
1389:Archived
1386:PDB 1JDG
1284:12182663
1240:10910965
1174:See also
1140:coal tar
1047:1600±710
981:2.7±0.52
831:Fluorene
760:Kanazawa
696:mutation
656:phase II
629:fluorene
449:fluorene
417:coal tar
104:205-12-9
25:brackets
1928:7 March
1868:Bibcode
1845:7039355
1795:7017394
1755:7 March
1749:epa.gov
1729:7 March
1556:8507106
1415:Bibcode
1370:7 March
1336:7 March
1307:7 March
1302:Pubchem
1160:mutagen
1057:890±170
903:960±320
851:550±140
755:Beijing
704:topical
664:sulfate
609:vehicle
549:epoxide
456:plane.
453:benzene
386:what is
384: (
332:Density
324:216.283
213:PubChem
1886:
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1077:Safety
861:160±72
782:summer
777:winter
772:summer
767:winter
708:tumors
561:CYP1A1
381:verify
378:
201:C19344
58:Names
1841:S2CID
1719:(PDF)
1560:S2CID
1517:S2CID
1168:feces
1032:292.8
1020:Total
987:0.053
975:0.254
957:40±12
951:215.5
928:0.099
923:99±18
918:0.093
913:93±49
876:0.005
871:57±22
866:0.013
824:BaPeq
814:BaPeq
804:BaPeq
794:BaPeq
676:urine
645:liver
545:P-450
496:in a
407:is a
115:ChEBI
1930:2016
1884:PMID
1833:PMID
1791:PMID
1757:2016
1731:2016
1698:PMID
1642:help
1621:2016
1595:PMID
1552:PMID
1481:help
1460:2016
1431:PMID
1372:2016
1338:2016
1309:2016
1280:PMID
1236:PMID
1062:0.29
1052:0.58
1042:3.05
969:13±5
963:0.79
908:0.96
898:26.9
856:0.04
836:0.08
819:pg/m
809:pg/m
799:pg/m
789:pg/m
728:coal
694:, a
674:and
672:bile
631:and
605:PAHs
589:edit
565:anti
555:The
433:KEGG
237:UNII
192:KEGG
144:8796
1919:doi
1915:229
1876:doi
1825:doi
1783:doi
1688:hdl
1678:doi
1587:doi
1544:doi
1509:doi
1423:doi
1272:doi
1226:doi
995:...
846:3.7
750:RPF
692:NER
666:or
569:syn
482:PAH
476:of
263:EPA
226:915
216:CID
1946::
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