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Mutagenic selectivity at the HPRT locus in V-79 cells: Comparison of mutations caused by bay-region benzo[a]pyrene 7,8-diol-9,10-epoxide enantiomers with high and low carcinogenic activity
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Chemical synthesis of a bay-region polycyclic aromatic hydrocarbon tetrahydroepoxide-deoxyadenosine adduct and its site-specific incorporation into a DNA oligomer
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Synthesis of deoxyadenosine adducts from the highly carcinogenic fjord region diol epoxide of benzo[c]phenanthrene
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0026692714
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Epoxide and diol epoxide adducts of polycyclic aromatic hydrocarbons at the exocyclic amino group of deoxyguanosine
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Lakshman, M.K.2
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18
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Synthesis of oligonucleotide adducts of bay region diol epoxide metabolites of carcinogenic polycyclic aromatic hydrocarbons
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Lakshman,M.K., Chaturvedi,S. and Lehr,R.E. (1994) Improved high-yield synthesis of polycyclic aromatic hydrocarbon amino tribenzoates, nucleophilic components for synthesis of diol epoxide-nucleoside adducts. Synth. Commun., 24, 2983-2988.
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Lakshman, M.K.1
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21
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0029971416
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A rapid, high-yield method for 5′-hydroxyl protection in very reactive and amino group modified nucleosides using dimethoxytrityl tetrafluoroborate
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Lakshman,M.K. and Zajc,B. (1996) A rapid, high-yield method for 5′-hydroxyl protection in very reactive and amino group modified nucleosides using dimethoxytrityl tetrafluoroborate. Nucleosides and Nucleotides, 15, 1029-1039.
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Lakshman, M.K.1
Zajc, B.2
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22
-
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12644302500
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-
note
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4 as external standard): 1c = 149.976-150.057: 2c = 150.025-150.076; 3c = 149.398, 149.258 (since 1c and 2c constitute a mixture of four diastereomers each, ranges for the phosphorus resonances are provided).
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23
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0025081293
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Synthesis of polycyclic aromatic hydrocarbon-nucleoside and oligonucleotide adducts specifically alkylated on the amino functions of deoxyguanosine and deoxyadenosine
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Lee,H., Hinz,M., Stezowski,J.J. and Harvey,R.G. (1990) Synthesis of polycyclic aromatic hydrocarbon-nucleoside and oligonucleotide adducts specifically alkylated on the amino functions of deoxyguanosine and deoxyadenosine. Tetrahedron Lett., 31, 6773-6776.
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Lee, H.1
Hinz, M.2
Stezowski, J.J.3
Harvey, R.G.4
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24
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0029091659
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6-amino group to (-)-(7R,8S,9R,10S)-7.8-dihydroxy-9,10-epoxy-7,8,9,10O-tetrahydrobenzo[a]pyrene
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6-amino group to (-)-(7R,8S,9R,10S)-7.8-dihydroxy-9,10-epoxy-7,8,9,10O-tetrahydrobenzo[a]pyrene. Biochemistry, 34, 9009-9020.
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Biochemistry
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Schurter, E.J.1
Sayer, J.M.2
Oh-hara, T.3
Yeh, H.J.C.4
Yagi, H.5
Luxon, B.A.6
Jerina, D.M.7
Gorenstein, D.G.8
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26
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0028278375
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Stepwise regeneration and recovery of deoxyribonucleoside phosphoramidite monomers during solid-phase oligonucleotide synthesis
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Scremin,C.L., Zhou,L., Srinivasachar,K. and Beaucage,S.L. (1994) Stepwise regeneration and recovery of deoxyribonucleoside phosphoramidite monomers during solid-phase oligonucleotide synthesis. J. Org. Chem., 59, 1963-1966.
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Scremin, C.L.1
Zhou, L.2
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Beaucage, S.L.4
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27
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0003074918
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Covalent nucleoside adducts of benzo[a]pyrene 7,8-diol 9,10-epoxides: Structural reinvestigation and characterization of a novel adenosine adduct on the ribose moiety
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Sayer,J.M. Chadha,A., Agarwal,S.K., Yeh,H.J.C., Yagi,H. and Jerina,D.M. (1991) Covalent nucleoside adducts of benzo[a]pyrene 7,8-diol 9,10-epoxides: structural reinvestigation and characterization of a novel adenosine adduct on the ribose moiety. J. Org. Chem., 56, 20-29.
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Sayer, J.M.1
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Yeh, H.J.C.4
Yagi, H.5
Jerina, D.M.6
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28
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12644306183
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We thank Dr. Barbara Zajc (University of Ljubljana) for the CD data of oligonucleotides containing BaP diol epoxide adducts at the exocyclic amino group of dG
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We thank Dr. Barbara Zajc (University of Ljubljana) for the CD data of oligonucleotides containing BaP diol epoxide adducts at the exocyclic amino group of dG.
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29
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0028943587
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6-amino group to (-)-(7S,8R,9R,10S)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydro-benzo[a]pyrene
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6-amino group to (-)-(7S,8R,9R,10S)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydro-benzo[a]pyrene. Biochemistry, 34, 1364-1375.
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Biochemistry
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Schurter, E.J.1
Yeh, H.J.C.2
Sayer, J.M.3
Lakshman, M.K.4
Yagi, H.5
Jerina, D.M.6
Gorenstein, D.G.7
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30
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0028927764
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Direct synthesis and characterization of site-specific adenosyl adducts derived from the binding of a 3,4-dihydroxy-1,2-epoxybenzo[c]phenanthrene stereoisomer to an 11-mer oligodeoxyribonucleotide
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Laryea,A., Cosman,M., Lin,J.-M., Liu,T., Agarwal,R., Smirnov,S., Amin,S., Harvey,R.G., Dipple,A. and Geacintov,N.E. (1995) Direct synthesis and characterization of site-specific adenosyl adducts derived from the binding of a 3,4-dihydroxy-1,2-epoxybenzo[c]phenanthrene stereoisomer to an 11-mer oligodeoxyribonucleotide. Chem. Res. Toxicol., 8, 444-454.
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Laryea, A.1
Cosman, M.2
Lin, J.-M.3
Liu, T.4
Agarwal, R.5
Smirnov, S.6
Amin, S.7
Harvey, R.G.8
Dipple, A.9
Geacintov, N.E.10
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31
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12644312489
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The apurinic site was created through the use of 'dSpacer' available from Glen Research, VA
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The apurinic site was created through the use of 'dSpacer' available from Glen Research, VA.
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32
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0001313197
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5′-Amino pyrene provides a sensitive, nonperturbing fluorescent probe of RNA secondary and tertiary structure formation
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Such an effect has been reported in a case unrelated to the present study, where pyrene was tethered at the 5′-terminus via a 5-atom linker: Kierzek,R., Li,Y., Turner,D.H. and Bevilacqua,P.C. (1993) 5′-Amino pyrene provides a sensitive, nonperturbing fluorescent probe of RNA secondary and tertiary structure formation. J. Am. Chem. Soc., 115. 4985-4992.
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Kierzek, R.1
Li, Y.2
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0029989672
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1H NMR
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1H NMR. Biochemistry, 35, 6212-6224.
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Zegar, I.S.1
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Horton, P.J.4
Harris, C.M.5
Harris, T.M.6
Stone, M.P.7
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34
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0028962081
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Multiple fluorescence lifetimes for oligonucleotides containing single, site-specific modifications at guanine and adenine corresponding to trans addition of exocyclic amino groups to (+)-(7R,8S,9S,10R)- And (-)-(7S,8R,9R,10S)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene
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and references therein
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LeBreton,P.R., Huang,C-R., Fernando,H., Zajc,B., Lakshman,M.K., Sayer,J.M. and Jerina,D.M. (1995) Multiple fluorescence lifetimes for oligonucleotides containing single, site-specific modifications at guanine and adenine corresponding to trans addition of exocyclic amino groups to (+)-(7R,8S,9S,10R)- and (-)-(7S,8R,9R,10S)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene. Chem. Res. Toxicol., 8, 338-348, and references therein.
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LeBreton, P.R.1
Huang, C.-R.2
Fernando, H.3
Zajc, B.4
Lakshman, M.K.5
Sayer, J.M.6
Jerina, D.M.7
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35
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0023189687
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Properties of covalent benzo[a]pyrene diol epoxide-DNA adducts investigated by fluorescence techniques
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Geacintov,N.E., Zinger,D., Ibanez,V., Santella,R., Grunberger,D. and Harvey,R.G. (1987) Properties of covalent benzo[a]pyrene diol epoxide-DNA adducts investigated by fluorescence techniques. Carcinogenesis, 8, 925-935.
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Geacintov, N.E.1
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Ibanez, V.3
Santella, R.4
Grunberger, D.5
Harvey, R.G.6
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36
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0021220028
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Spectroscopic studies of DNA complexes formed after reaction with anti-benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide enantiomers of different carcinogenic potency
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Jernström,B., Lycksell,P.-O., Gräslund,A. and Nordén,B. (1984) Spectroscopic studies of DNA complexes formed after reaction with anti-benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide enantiomers of different carcinogenic potency. Carcinogenesis, 5, 1129-1135.
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Jernström, B.1
Lycksell, P.-O.2
Gräslund, A.3
Nordén, B.4
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