Chemical carcinogenesis. 93. Synthesis of potential phenolic metabolites of benzo[b]fluoranthene

Amin, Shantu; Huie, Keith; Hussain, Nalband; Balanikas, George; Carmella, Steven G.; Hecht, Stephen S.

doi:10.1021/jo00358a009

Cited by 18 publications

(8 citation statements)

References 5 publications

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“…(28) 13 (29) (30) 13 (34) (35) ARG225, TRP222, GLU219, LEU218, ILE215, ILE202, MET199, ALA198, THR196, PRO193, LYS165, MET161, TYR158, ALA157, MET155, ARG153, PHE149, SER123 …”

Section: 24mentioning

confidence: 99%

Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth

Chollet

Mori

Menendez

et al. 2015

European Journal of Medicinal Chemistry

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A series of fluorene-based derivatives was synthesized and evaluated for inhibiting both InhA and Mycobacterium tuberculosis growth. These compounds were inspired by the previously reported Genz-10850 molecule, a good InhA inhibitor, but with a poor activity against M. tuberculosis growth. Structure-activity relationships were performed by introducing the following chemical modifications: 1) the piperazine ring; 2) the amide group; 3) the aryl moiety; and 4) the fluorene moiety. Among these new derivatives, one of them was more effective against both the InhA activity and mycobacterial growth, compared to the hit compound. Docking studies were also performed to rationalize activities of these derivatives. Furthermore, we showed for the first time that efflux pump inhibitors potentiated the efficacy of Genz-10850 (GEQ) derivatives against M. tuberculosis growth, demonstrating that these compounds could be substrates of some efflux pumps.

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“…(28) 13 (29) (30) 13 (34) (35) ARG225, TRP222, GLU219, LEU218, ILE215, ILE202, MET199, ALA198, THR196, PRO193, LYS165, MET161, TYR158, ALA157, MET155, ARG153, PHE149, SER123 …”

Section: 24mentioning

confidence: 99%

Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth

Chollet

Mori

Menendez

et al. 2015

European Journal of Medicinal Chemistry

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“…Both of these substances are known to be carcinogenic 51. Moreover, some of their transformation products were also identified as being carcinogenic 58, 59. There was an absence of peaks at RT 43 and 45 min in soil sample 3I but the most predominant peaks at RT of 61 and 63 min were stronger (most resistant) than for any of the other samples.…”

Section: Resultsmentioning

confidence: 94%

Data evaluation of tar oil degradation using comprehensive GC²/ MS: individual compounds and principal component analysis

Vasilieva

Janik²,

Scherr

et al. 2012

J of Chemical Tech & Biotech

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BACKGROUND: Coal tar is a complex mixture of more than 100 compounds, including polycyclic aromatic hydrocarbons (PAHs), alkylated PAHs, phenolic as well as NSO‐heterocyclic compounds (HAC). Many of these are associated with human and environmental risk. Information concerning the environmental fate of coal tar constituents, apart from the 16 PAHs listed as priority substances by the US‐EPA, is scarce. In the current study, aerobic degradation of aromatic tar oil constituents in ten historically contaminated soils was monitored under laboratory conditions using two‐dimensional comprehensive GC2/ MS. RESULTS: Fifty‐four aromatic compounds were detected in one single analysis. Degradation behavior of individual compounds was determined by their hydrophobicity, molecular size, degree of alkylation and isomeric conformation. Eight substances, including six US‐EPA PAHs and two benzofluorene isomers, were identified in nine out of ten soils as principal components in the residual contamination after degradation. CONCLUSION: Using GC2/ MS to reveal the degradation behavior of distinct coal tar constituents and applying PCA to identify contaminants resistant to microbial degradation can be useful for the optimization of bioremediation measures at contaminated sites. Copyright © 2012 Society of Chemical Industry

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“…(±)‐ anti ‐Benzo[ a ]pyrene‐7,8‐dihydrodiol‐9,10‐epoxide (B[ a ]PDE) was purchased from the National Cancer Institute (NCI) Chemical Carcinogen Reference Standard Repository (Midwest Research Institute, Kansas City, MI, USA). (±)‐ anti ‐Benzo[ b ]fluoranthene‐9,10‐dihydrodiol‐11,12‐epoxide (B[ b ]FDE),39–43 (±)‐ anti ‐dibenzo[ a,l ]pyrene‐11,12‐dihydrodiol‐13,14‐epoxide (DB[ a,l ]PDE)44 and (±)‐ anti ‐dibenz[ a,h ]anthracene‐3,4‐dihydrodiol‐1,2‐epoxide ( DB[ a,h ]ADE)40, 45, 46 were synthesised according to methods described previously. Caution : PAH‐dihydrodiol epoxides are mutagens and carcinogens.…”

Section: Methodsmentioning

confidence: 99%

Cover Picture: Manipulating Catalytic Pathways: Deoxygenation of Palmitic Acid on Multifunctional Catalysts (Chem. Eur. J. 15/2013)

Peng

Zhao

Kasakov

et al. 2013

Chemistry A European J

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Chemical carcinogenesis. 93. Synthesis of potential phenolic metabolites of benzo[b]fluoranthene

Cited by 18 publications

References 5 publications

Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth

Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth

Data evaluation of tar oil degradation using comprehensive GC²/ MS: individual compounds and principal component analysis

Cover Picture: Manipulating Catalytic Pathways: Deoxygenation of Palmitic Acid on Multifunctional Catalysts (Chem. Eur. J. 15/2013)

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Chemical carcinogenesis. 93. Synthesis of potential phenolic metabolites of benzo[b]fluoranthene

Cited by 18 publications

References 5 publications

Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth

Design, synthesis and evaluation of new GEQ derivatives as inhibitors of InhA enzyme and Mycobacterium tuberculosis growth

Data evaluation of tar oil degradation using comprehensive GC2/ MS: individual compounds and principal component analysis

Cover Picture: Manipulating Catalytic Pathways: Deoxygenation of Palmitic Acid on Multifunctional Catalysts (Chem. Eur. J. 15/2013)

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Data evaluation of tar oil degradation using comprehensive GC²/ MS: individual compounds and principal component analysis