메뉴 건너뛰기




Volumn 25, Issue 5, 2005, Pages 371-391

Syntheses of adducts of active metabolites of carcinogenic polycyclic aromatic hydrocarbons with 2′-deoxyribonucleosides

Author keywords

13C benzo a pyrene; 13C BP 7,8 diol; 13C BPQ; 15N labelled BPQ guanosine adduct; Benzo a pyrene 7,8 dione (BPQ); PAH 2 deoxyribonucleoside adducts; Radical cation adducts of benzo a pyrene

Indexed keywords

METABOLITES; POSITIVE IONS; PYRENE;

EID: 29244472855     PISSN: 10406638     EISSN: 15635333     Source Type: Journal    
DOI: 10.1080/10406630500447019     Document Type: Article
Times cited : (16)

References (31)
  • 2
    • 0020431144 scopus 로고
    • Induction of Microsomal Enzymes by Foreign Chemicals and Carcinogenesis by Polycyclic Aromatic Hydrocarbons
    • A. H. Conney, Induction of Microsomal Enzymes by Foreign Chemicals and Carcinogenesis by Polycyclic Aromatic Hydrocarbons, Cancer Res. 42 (1982):4875-4917.
    • (1982) Cancer Res. , vol.42 , pp. 4875-4917
    • Conney, A.H.1
  • 3
    • 0028707724 scopus 로고
    • Reactions of Polycyclic Aromatic Hydrocarbons with DNA
    • Hemminki, K., Dipple, A., Segerbäck, D., Kadulbar, F. F., Shuker, D., Bartsch, H. (Eds.) IARC Scientific Publication No. 125
    • A. Dipple, Reactions of Polycyclic Aromatic Hydrocarbons with DNA. In DNA Adducts: Identification and Biological Significance, Hemminki, K., Dipple, A., Segerbäck, D., Kadulbar, F. F., Shuker, D., Bartsch, H. (Eds.) IARC Scientific Publication No. 125 (1994) pp. 107-129.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 107-129
    • Dipple, A.1
  • 5
    • 0017593561 scopus 로고
    • Characterization of Nucleoside Adducts from the in Vitro Reaction of Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide or Benzo[a]pyrene-4,5-oxide with Nucleic Acids
    • K. Jennette, A. M. Jeffrey, S. H. Blobstein, F. A. Beland, R. G. Harvey, and I. B. Weinstein, Characterization of Nucleoside Adducts from the in Vitro Reaction of Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide or Benzo[a]pyrene-4,5- oxide with Nucleic Acids, Biochemistry 16 (1977):932-938.
    • (1977) Biochemistry , vol.16 , pp. 932-938
    • Jennette, K.1    Jeffrey, A.M.2    Blobstein, S.H.3    Beland, F.A.4    Harvey, R.G.5    Weinstein, I.B.6
  • 6
    • 0022974550 scopus 로고
    • Regio- and Stereospecificity of Homogeneous 3α-Hydroxysteroid- Dihydrodiol Dehydrogenase for trans-Dihydrodiol Metabolites of Polycyclic Aromatic Hydrocarbons
    • T. E. Smithgall, R. G. Harvey, and T. M. Penning, Regio- and Stereospecificity of Homogeneous 3α-Hydroxysteroid-Dihydrodiol Dehydrogenase for trans-Dihydrodiol Metabolites of Polycyclic Aromatic Hydrocarbons, J. Biol. Chem. 261 (1986):6184-6191.
    • (1986) J. Biol. Chem. , vol.261 , pp. 6184-6191
    • Smithgall, T.E.1    Harvey, R.G.2    Penning, T.M.3
  • 7
    • 0023835621 scopus 로고
    • Oxidation of the trans-3,4-Dihydrodiol Metabolites of the Potent Carcinogen 7,12-Dimethylbenz[a]anthracene and Other Benz[a]anthracene Derivatives by 3α-Hydroxysteroid-Dihydrodiol Dehydrogenase: Effects of Methyl Substitution on Velocity and Stereochemical Course of trans-Dihydrodiol Oxidation
    • T. E. Smithgall, R. G. Harvey, and T. M. Penning, Oxidation of the trans-3,4-Dihydrodiol Metabolites of the Potent Carcinogen 7,12-Dimethylbenz[a] anthracene and Other Benz[a]anthracene Derivatives by 3α-Hydroxysteroid- Dihydrodiol Dehydrogenase: Effects of Methyl Substitution on Velocity and Stereochemical Course of trans-Dihydrodiol Oxidation, Cancer Res. 48 (1988):1227-1232.
    • (1988) Cancer Res. , vol.48 , pp. 1227-1232
    • Smithgall, T.E.1    Harvey, R.G.2    Penning, T.M.3
  • 8
    • 0023907050 scopus 로고
    • Spectroscopic Identification of ortho-Quinones as the Products of Polycyclic Aromatic trans-Dihydrodiol Oxidation Catalyzed by Dihydrodiol Dehydrogenase: A Potential Route of Proximate Carcinogen Metabolism
    • T. E. Smithgall, R. G. Harvey, and T. M. Penning, Spectroscopic Identification of ortho-Quinones as the Products of Polycyclic Aromatic trans-Dihydrodiol Oxidation Catalyzed by Dihydrodiol Dehydrogenase: A Potential Route of Proximate Carcinogen Metabolism, J.Biol.Chem. 263 (1988):1814-1820.
    • (1988) J.Biol.Chem. , vol.263 , pp. 1814-1820
    • Smithgall, T.E.1    Harvey, R.G.2    Penning, T.M.3
  • 9
    • 0029080079 scopus 로고
    • Central Role of Radical Cations in Metabolic Activation of Polycyclic Aromatic Hydrocarbons
    • E. L. Cavalieri and E. G. Rogan, Central Role of Radical Cations in Metabolic Activation of Polycyclic Aromatic Hydrocarbons, Xenobiotica 25 (1995):677-688.
    • (1995) Xenobiotica , vol.25 , pp. 677-688
    • Cavalieri, E.L.1    Rogan, E.G.2
  • 10
    • 0032832051 scopus 로고    scopus 로고
    • Cancer Initiation by Polycyclic Aromatic Hydrocarbons Results from Formation of Stable DNA Adducts Rather than Apurinic Sites
    • The biological relevance of the radical-cation pathway is disputed: Melendez-Colon, V., Luch, A., Seidel, A., Baird, W. Cancer Initiation by Polycyclic Aromatic Hydrocarbons Results from Formation of Stable DNA Adducts Rather than Apurinic Sites, Carcinogenesis 20 (1999):1885-1891.
    • (1999) Carcinogenesis , vol.20 , pp. 1885-1891
    • Melendez-Colon, V.1    Luch, A.2    Seidel, A.3    Baird, W.4
  • 11
    • 0027281455 scopus 로고
    • Reactivity of Benzo[a]pyrene-7,8-dione with DNA. Evidence for the Formation of Deoxyguanosine Adducts
    • M. Shou, R. G. Harvey, and T. M. Penning, Reactivity of Benzo[a]pyrene-7,8-dione with DNA. Evidence for the Formation of Deoxyguanosine Adducts, Carcinogenesis 14 (1993):475-482.
    • (1993) Carcinogenesis , vol.14 , pp. 475-482
    • Shou, M.1    Harvey, R.G.2    Penning, T.M.3
  • 12
    • 0033024560 scopus 로고    scopus 로고
    • Synthesis and Characterization of Polycyclic Aromatic Hydrocarbon o-Quinone Depurinating N7-Guanine Adducts
    • K. D. McCoull, D. Rindgen, I. A. Blair, and T. M. Penning, Synthesis and Characterization of Polycyclic Aromatic Hydrocarbon o-Quinone Depurinating N7-Guanine Adducts, Chem. Res. Toxicol. 12 (1999):237-246.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 237-246
    • McCoull, K.D.1    Rindgen, D.2    Blair, I.A.3    Penning, T.M.4
  • 13
    • 3042727183 scopus 로고    scopus 로고
    • Identification and Characterization of Novel Stable Deoxyguanosine and Deoxyadenosine Adducts of Benzo[a]pyrene-7,8-quinone from Reactions at Physiological pH
    • N. Balu, W. T. Padgett, G. R. Lambert, A. E. Swank, A. M. Richard, and S. Nesnow, Identification and Characterization of Novel Stable Deoxyguanosine and Deoxyadenosine Adducts of Benzo[a]pyrene-7,8-quinone from Reactions at Physiological pH, Chem. Res. Toxicol. 17 (2004):827-838.
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 827-838
    • Balu, N.1    Padgett, W.T.2    Lambert, G.R.3    Swank, A.E.4    Richard, A.M.5    Nesnow, S.6
  • 14
    • 4844231886 scopus 로고    scopus 로고
    • Efficient New Syntheses of Polycyclic Aromatic Hydrocarbon Ortho-Quinones and their 2′-Deoxyribonucleoside Adducts
    • R. G. Harvey, Q. Dai, C. Ran, S. R. Gopishetty, and T. M. Penning, Efficient New Syntheses of Polycyclic Aromatic Hydrocarbon Ortho-Quinones and their 2′-Deoxyribonucleoside Adducts, Polycyclic Arom. Compds. 24 (2004):257-269.
    • (2004) Polycyclic Arom. Compds. , vol.24 , pp. 257-269
    • Harvey, R.G.1    Dai, Q.2    Ran, C.3    Gopishetty, S.R.4    Penning, T.M.5
  • 15
    • 18244362791 scopus 로고    scopus 로고
    • Synthesis of Adducts of o-Quinone Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons with 2′-Deoxyribonucleosides
    • Q. Dai, C. Ran, and R. G. Harvey, Synthesis of Adducts of o-Quinone Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons with 2′-Deoxyribonucleosides, Org. Lett. 7 (2005):999-1002.
    • (2005) Org. Lett. , vol.7 , pp. 999-1002
    • Dai, Q.1    Ran, C.2    Harvey, R.G.3
  • 16
    • 1542549038 scopus 로고
    • Amination of Naphthoquinones with Azidotrimethylsilane
    • B. Husu, S. Kafka, Z. Kadunc, and M. Tisler, Amination of Naphthoquinones with Azidotrimethylsilane, Monat. Chem. 119 (1988):215-222.
    • (1988) Monat. Chem. , vol.119 , pp. 215-222
    • Husu, B.1    Kafka, S.2    Kadunc, Z.3    Tisler, M.4
  • 17
    • 0034712156 scopus 로고    scopus 로고
    • Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates
    • J. P. Wolfe, H. Tomori, J. P. Sadighi, J. Yin, and S. L. Buchwald, Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates, J. Org. Chem. 65 (2000):1158-1174.
    • (2000) J. Org. Chem. , vol.65 , pp. 1158-1174
    • Wolfe, J.P.1    Tomori, H.2    Sadighi, J.P.3    Yin, J.4    Buchwald, S.L.5
  • 18
    • 18244406891 scopus 로고    scopus 로고
    • Chemistry of Polycyclic Aromatic Hydrocarbons (PAH) o-Quinones Generated by the Aldo-Keto Reductase Pathway of PAH Activation
    • Penning, T. M., Petrash, J. M. (Eds.) ACS Symposium Series 865, American Chemical Society. Washington, DC
    • S. R. Gopishetty, R. G. Harvey, S. H. Lee, I. A. Blair, and T. M. Penning, Chemistry of Polycyclic Aromatic Hydrocarbons (PAH) o-Quinones Generated by the Aldo-Keto Reductase Pathway of PAH Activation, In Aldo-Keto Reductases and Toxicant Metabolism; Penning, T. M., Petrash, J. M. (Eds.) ACS Symposium Series 865, American Chemical Society. Washington, DC (2004) pp. 127-137.
    • (2004) Aldo-Keto Reductases and Toxicant Metabolism , pp. 127-137
    • Gopishetty, S.R.1    Harvey, R.G.2    Lee, S.H.3    Blair, I.A.4    Penning, T.M.5
  • 19
    • 0016905198 scopus 로고
    • Synthesis of Hydroquinone Diacetates from Polycyclic Aromatic Quinones
    • H. Cho and R. G. Harvey, Synthesis of Hydroquinone Diacetates from Polycyclic Aromatic Quinones, J. Chem. Soc Perkin Trans. I. (1976):836-839.
    • (1976) J. Chem. Soc Perkin Trans. I , pp. 836-839
    • Cho, H.1    Harvey, R.G.2
  • 20
    • 85197348462 scopus 로고    scopus 로고
    • note
    • Although PAH catechols are susceptible to auto-oxidation, their diester or diether derivatives are generally stable in air.
  • 21
    • 1642272391 scopus 로고    scopus 로고
    • Syntheses of the o-Quinones and Other Oxidized Metabolites of Polycyclic Aromatic Hydrocarbons Implicated in Carcinogenesis
    • R. G. Harvey, Q. Dai, C. Ran, and T. M. Penning, Syntheses of the o-Quinones and Other Oxidized Metabolites of Polycyclic Aromatic Hydrocarbons Implicated in Carcinogenesis, J. Org. Chem. 69 (2004):2024-2032.
    • (2004) J. Org. Chem. , vol.69 , pp. 2024-2032
    • Harvey, R.G.1    Dai, Q.2    Ran, C.3    Penning, T.M.4
  • 22
    • 0141745119 scopus 로고    scopus 로고
    • 9-Derivatives of N6-[(Dimethylamino)methylene]adenine Bearing an Active Methylene Group and their Further Derivatization Leading to α-Branched Acyclic Nucleoside Analogues
    • 9-Derivatives of N6-[(Dimethylamino)methylene]adenine Bearing an Active Methylene Group and their Further Derivatization Leading to α-Branched Acyclic Nucleoside Analogues, Eur. J. Org. Chem. (1999):2675-2682.
    • (1999) Eur. J. Org. Chem. , pp. 2675-2682
    • Hockova, D.1    Budesinsky, M.2    Marek, R.3    Marek, J.4    Holy, A.5
  • 23
    • 33845551079 scopus 로고
    • Efficient Synthesis of Non-K-Region Trans-dihydrodiols of Polycyclic Aromatic Hydrocarbons from o-Quinones and Catechols
    • K. L. Platt and F. Oesch, Efficient Synthesis of Non-K-Region Trans-dihydrodiols of Polycyclic Aromatic Hydrocarbons from o-Quinones and Catechols, J. Org. Chem. 48 (1983):265-267.
    • (1983) J. Org. Chem. , vol.48 , pp. 265-267
    • Platt, K.L.1    Oesch, F.2
  • 25
    • 0032877481 scopus 로고    scopus 로고
    • Synthesis and Structure Determination of the Adducts Formed by Electrochemical Oxidation of Dibenzo[a, l]pyrene in the Presence of Adenine
    • K.-M. Li, J. Byun, M. L. Gross, D. Zamzow, R. Jankowiak, E. G. Rogan, and E. L. Cavalieri, Synthesis and Structure Determination of the Adducts Formed by Electrochemical Oxidation of Dibenzo[a, l]pyrene in the Presence of Adenine, Chem. Res. Toxicol. 12 (1999):749-757.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 749-757
    • Li, K.-M.1    Byun, J.2    Gross, M.L.3    Zamzow, D.4    Jankowiak, R.5    Rogan, E.G.6    Cavalieri, E.L.7
  • 26
    • 0031772349 scopus 로고    scopus 로고
    • Synthesis of Adducts Formed by Iodine Oxidation of Aromatic Hydrocarbons in the Presence of Deoxyribonucleosides and Nucleobases
    • A. A. Hanson, E. G. Rogan, and E. L. Cavalieri, Synthesis of Adducts Formed by Iodine Oxidation of Aromatic Hydrocarbons in the Presence of Deoxyribonucleosides and Nucleobases, Chem. Res. Toxicol. 11 (1998):1201-1208.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 1201-1208
    • Hanson, A.A.1    Rogan, E.G.2    Cavalieri, E.L.3
  • 29
    • 21144434859 scopus 로고    scopus 로고
    • Identification and Quantification of the Depurinating Adducts Formed in Mouse Skin Treated with Dibenzo[a, l]pyrene (DB[a, l]P) or Its Metabolites and in Rat Mammary Gland Treated with DB[a, l]P
    • E. L. Cavalieri, E. G. Rogan, K.-M. Li, R. Todorovic, F. Ariese, R. Jankowiak, N. Grubor, and G. J. Small, Identification and Quantification of the Depurinating Adducts Formed in Mouse Skin Treated with Dibenzo[a, l]pyrene (DB[a, l]P) or Its Metabolites and in Rat Mammary Gland Treated with DB[a, l]P, Chem. Res. Toxicol. 18 (2005):976-983.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 976-983
    • Cavalieri, E.L.1    Rogan, E.G.2    Li, K.-M.3    Todorovic, R.4    Ariese, F.5    Jankowiak, R.6    Grubor, N.7    Small, G.J.8
  • 30
    • 0042009118 scopus 로고    scopus 로고
    • Efficient One-Step Suzuki Arylation of Unprotected Halonucleosides, Using Water-soluble Palladium Catalysts
    • E. C. Western, J. R. Daft, E. M. Johnson, P. M. Gannett, and K. H. Shaughnessy, Efficient One-Step Suzuki Arylation of Unprotected Halonucleosides, Using Water-soluble Palladium Catalysts, J. Org. Chem. 68 (2003):6767-6774.
    • (2003) J. Org. Chem. , vol.68 , pp. 6767-6774
    • Western, E.C.1    Daft, J.R.2    Johnson, E.M.3    Gannett, P.M.4    Shaughnessy, K.H.5
  • 31
    • 16844367937 scopus 로고    scopus 로고
    • Catalysts for Suzuki-Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand Structure
    • T. E. Barder, S. D. Walker, and J. R. Martinelli, and S. L. Buchwald, Catalysts for Suzuki-Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand Structure, J. Am. Chem. Soc. 127 (2005):4685-4696.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 4685-4696
    • Barder, T.E.1    Walker, S.D.2    Martinelli, J.R.3    Buchwald, S.L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.