Reactions of deoxyribonucleotide bases with sulfooxymethyl or halomethyl polycyclic aromatic hydrocarbons induce unwinding of DNA supercoils

References

• Ames BN, Durston WE, Yamasaki E, Lee FD. 1973. Carcinogens are mutagens: a simple test system combining liver homogenates for activation and bacteria for detection. Proc Natl Acad Sci USA. 70(8):2281–2285. doi: 10.1073/PNAS.70.8.2281.
   PubMed Web of Science ®Google Scholar
• Anania C, Lupiáñez DG. 2020. Order and disorder: abnormal 3D chromatin organization in human disease. Brief Funct Genomics. 19(2):128–138. doi: 10.1093/bfgp/elz028.
   PubMed Web of Science ®Google Scholar
• Baranello L, Levens D, Gupta A, Kouzine F. 2012. The importance of being supercoiled: how DNA mechanics regulate dynamic processes. Biochim Biophys Acta. 1819(7):632–638. doi: 10.1016/j.bbagrm.2011.12.007.
   PubMed Web of Science ®Google Scholar
• Bendadani C, Meinl W, Monien BH, Dobbernack G, Glatt H. 2014. The carcinogen 1-methylpyrene forms benzylic DNA adducts in mouse and rat tissues in vivo via a reactive sulphuric acid ester. Arch Toxicol. 88(3):815–821. doi: 10.1007/s00204-013-1182-6.
   PubMed Web of Science ®Google Scholar
• Bendadani C, Steinhauser L, Albert K, Glatt H, Monien BH. 2016. Metabolism and excretion of 1-hydroxymethylpyrene, the proximate metabolite of the carcinogen 1-methylpyrene, in rats. Toxicology. 366–367:43–52. doi: 10.1016/j.tox.2016.08.006.
   PubMed Web of Science ®Google Scholar
• Bjornsti MA, Kaufmann SH. 2019. Topoisomerases and cancer chemotherapy: recent advances and unanswered questions. F1000Res. 8:1704. doi: 10.12688/f1000research.20201.1.
   Google Scholar
• Braga RS, Barone PMVB, Galvão DS. 2000. Identifying carcinogenic activity of methylated and non-methylated polycyclic aromatic hydrocarbons (PAHs) through electronic and topological indices. Braz J Phys. 30(3):560–568. doi: 10.1590/S0103-97332000000300013.
   Web of Science ®Google Scholar
• Brosh R. 2013. DNA helicases involved in DNA repair and their roles in cancer. Nat Rev Cancer. 13(8):542–558. doi: 10.1038/nrc3560.
   PubMed Web of Science ®Google Scholar
• Buckner JC, Malkin MG, Reed E, Cascino TL, Reid JM, Ames MM, Tong WP, Lim S, Figg WD. 1999. Phase II study of antineoplastons A10 (NSC 648539) and AS2-1 (NSC 620261) in patients with recurrent glioma. Mayo Clin Proc. 74(2):137–145. doi: 10.4065/74.2.137.
   PubMed Web of Science ®Google Scholar
• Burzynski SR. 2004. The present state of Antineoplaston research (1). Integr Cancer Ther. 3(1):47–58. doi: 10.1177/1534735403261964.
   PubMedGoogle Scholar
• Cavalieri E, Rogan E. 1985. Role of radical cations in aromatic hydrocarbon carcinogenesis. Environ Health Perspect. 64:69–84. doi: 10.1289/ehp.856469.
   PubMed Web of Science ®Google Scholar
• Cavalieri E, Rogan E. 2014. The molecular etiology and prevention of estrogen-initiated cancers: Ockham’s Razor: pluralitas non est ponenda sine necessitate. Plurality should not be posited without necessity. Mol Aspects Med. 36:1–55. doi: 10.1016/j.mam.2013.08.002.
   PubMed Web of Science ®Google Scholar
• Cavalieri EL, Rogan EG. 2016. Depurinating estrogen-DNA adducts, generators of cancer initiation: their minimization leads to cancer prevention. Clin Transl Med. 5(1):12. doi: 10.1186/s40169-016-0088-3.
   PubMedGoogle Scholar
• Celedon A, Wirtz D, Sun S. 2010. Torsional mechanics of DNA are regulated by small-molecule intercalation. J Phys Chem B. 114(50):16929–16935. doi: 10.1021/jp107541q.
   PubMed Web of Science ®Google Scholar
• Chakravarti D, Pelling JC, Cavalieri EL, Rogan EG. 1995. Relating aromatic hydrocarbon-induced DNA adducts and c-H-ras mutations in mouse skin papillomas: the role of apurinic sites. Proc Natl Acad Sci U S A. 92(22):10422–10426. doi: 10.1073/PNAS.92.22.10422.
   PubMed Web of Science ®Google Scholar
• Clark DJ, Leblanc BP. 2015. Analysis of DNA supercoiling induced by DNA–protein interactions. In: leblanc B, Rodrigue S, editors, DNA-protein interactions. Methods in molecular biology, vol 1334. New York, NY: Humana Press.
   Google Scholar
• Corless S, Gilbert N. 2017. Investigating DNA supercoiling in eukaryotic genomes. Brief Funct Genomics. 16(6):379–389. doi: 10.1093/bfgp/elx007.
   PubMed Web of Science ®Google Scholar
• Cox PM, Goding CR. 1991. Transcription and cancer. Br J Cancer. 63(5):651–662. doi: 10.1038/bjc.1991.151.
   PubMed Web of Science ®Google Scholar
• Dautant A, Langlois d‘ Estaintot B, Gallois B, Brown T, Hunter WN. 1995. A trigonal form of the idarubicin:d(CGATCG) complex; crystal and molecular structure at 2.0 A resolution. Nucleic Acids Res. 23(10):1710–1716. doi: 10.1093/nar/23.10.1710.
   PubMed Web of Science ®Google Scholar
• Del Mundo IMA, Vasquez KM, Wang G. 2019. Modulation of DNA structure formation using small molecules. Biochim Biophys Acta Mol Cell Res. 1866(12):118539. doi: 10.1016/j.bbamcr.2019.118539.
   PubMed Web of Science ®Google Scholar
• Dong S, Hwang HM, Shi X, Holloway L, Yu H. 2000. UVA-induced DNA single-strand cleavage by 1-hydroxypyrene and formation of covalent adducts between DNA and 1-hydroxypyrene. Chem Res Toxicol. 13(7):585–593. doi: 10.1021/tx990199x.
   PubMed Web of Science ®Google Scholar
• Fanick E, Kroll S. 2018. Polycyclic aromatic hydrocarbons in diesel engine exhaust both with and without after treatment. SAE Technical Paper 2018-01-1812. doi: 10.4271/2018-01-1812.
   Google Scholar
• Feng Z, Hu W, Chen JX, Pao A, Li H, Rom W, Hung MC, Tang MS. 2002. Preferential DNA damage and poor repair determine ras gene mutational hotspot in human cancer. J Natl Cancer Inst. 94(20):1527–1536. doi: 10.1093/jnci/94.20.1527.
   PubMedGoogle Scholar
• Flesher JW. 1995. Complete carcinogenic potential of polycyclic fluoranthene hydrocarbons in relation to their center or centers of highest electron density. Polycyclic Aromat Compd. 5(1-4):59–67. doi: 10.1080/10406639408015156.
   Google Scholar
• Flesher JW, Horn J, Lehner AF. 1996. Molecular modeling of carcinogenic potential in polycyclic hydrocarbons. J. Molecular Structure Theochem. 362(1):29–49. doi: 10.1016/0166-1280(95)04388-8.
   Web of Science ®Google Scholar
• Flesher JW, Horn J, Lehner AF. 1997a. 7-Sulfooxymethyl-12-methylbenz[a]anthracene is an exceptionally reactive electrophilic mutagen and ultimate carcinogen. Biochem Biophys Res Commun. 231(1):144–148. doi: 10.1006/BBRC.1997.6049.
   PubMed Web of Science ®Google Scholar
• Flesher JW, Horn J, Lehner AF. 1997b. 6-sulfooxymethylbenzo[a]pyrene is an ultimate electrophilic and carcinogenic form of the intermediary metabolite 6-hydroxymethylbenzo[a]pyrene. Biochem Biophys Res Commun. 234(3):554–558. doi: 10.1006/BBRC.1997.6679.
   PubMed Web of Science ®Google Scholar
• Flesher JW, Horn J, Lehner AF. 1997c. 7-Sulfooxymethylbenz[a]anthracene is an ultimate electrophilic and carcinogenic form of 7-hydroxymethylbenz[a]anthracene. Biochem Biophys Res Commun. 231(3):712–716. doi: 10.1006/BBRC.1997.6172.
   PubMed Web of Science ®Google Scholar
• Flesher JW, Horn J, Lehner AF. 1998a. 9-Sulfooxymethylanthracene is an ultimate electrophilic and carcinogenic form of 9-hydroxymethylanthracene. Biochem Biophys Res Commun. 251(1):239–243. doi: 10.1006/bbrc.1998.9448.
   PubMed Web of Science ®Google Scholar
• Flesher JW, Horn J, Lehner AF. 1998b. Carcinogenicity of 1-hydroxy-3-methylcholanthrene and its electrophilic sulfate ester 1-sulfooxy-3-methylcholanthrene in Sprague-Dawley rats. Biochem Biophys Res Commun. 243(1):30–35. doi: 10.1006/BBRC.1997.8048.
   PubMed Web of Science ®Google Scholar
• Flesher JW, Lehner AF. 2016. Structure, function and carcinogenicity of metabolites of methylated and non-methylated polycyclic aromatic hydrocarbons: a comprehensive review. Toxicol Mech Methods. 26(3):151–179. doi: 10.3109/15376516.2015.1135223.
   PubMed Web of Science ®Google Scholar
• Flesher JW, Lehner AF. 2019. The structural basis for the production of cancer and detoxification by oxidized metabolites of mesoanthracenic methylated and non-methylated polynuclear hydrocarbons: a paradigm shift. Ref J Chem. 9(4):197–254. doi: 10.1134/S2079978019040022.
   Google Scholar
• Flesher JW, Myers SR. 1990. Bioalkylation of benz[a]anthracene as a biochemical probe for carcinogenic activity. Lack of bioalkylation in a series of six noncarcinogenic polynuclear aromatic hydrocarbons. Drug Metab Dispos. 18:163–167. Corpus ID: 21148495.
   PubMed Web of Science ®Google Scholar
• Flesher JW, Myers SR. 1991. Rules of molecular geometry for predicting carcinogenic activity of unsubstituted polynuclear aromatic hydrocarbons. Teratog Carcinog Mutagen. 11(1):41–54. doi: 10.1002/tcm.1770110106.
   PubMedGoogle Scholar
• Flesher JW, Myers SR, Stansbury KH. 1990. The site of substitution of the methyl group in the bioalkylation of benzo[a]pyrene. Carcinogenesis. 11(3):493–496. doi: 10.1093/CARCIN/11.3.493.
   PubMed Web of Science ®Google Scholar
• Flesher JW, Sydnor KL. 1971. Carcinogenicity of derivatives of 7,12-dimethylbenz(a)anthracene. Cancer Res. 31:1951–1954. PMID: 5120292.
   PubMed Web of Science ®Google Scholar
• Flesher JW, Sydnor KL. 1973. Possible role of 6-hydroxymethylbenzo(a)pyrene as a proximate carcinogen of benzo(a)pyrene and 6-methylbenzo(a)pyrene. Int J Cancer. 11(2):433–437. doi: 10.1002/ijc.2910110221.
   PubMed Web of Science ®Google Scholar
• Flesher JW, Tay LK. 1978. Reactions of the carcinogens 7-hydroxymethyl-12-methylbenz(A)anthracene and 7-acetoxymethyl-12-methylbenz(A)anthracene with DNA. Res Commun Chem Pathol Pharmacol. 22:345–355. Corpus ID: 3059338
   PubMedGoogle Scholar
• Gao YG, Wang AHJ. 1991. Influence of aglycone modifications on the binding of anthracycline drugs to DNA: the molecular structure of idarubicin and 4-O-demethyl-11-deoxydoxorubicin complexed to d(CGATCG). Anti-Cancer Drug Des. 6:137–149. doi: 10.2210/PDB1D37/PDB.
   PubMedGoogle Scholar
• Geacintov NE, Broyde S. 2017. Repair-resistant DNA lesions. Chem Res Toxicol. 30(8):1517–1548. doi: 10.1021/acs.chemrestox.7b00128.
   PubMed Web of Science ®Google Scholar
• Glusker JP, Zacharias DE, Carrell HL. 1976. Molecular structures of the chemical carcinogens 7-chloromethylbenz(a)anthracene and 7-chloromethyl-12-methylbenz(a)anthracene. Cancer Res. 36:2428–2435.
   PubMed Web of Science ®Google Scholar
• Goldman R, Enewold L, Pellizzari E, Beach JB, Bowman ED, Krishnan SS, Shields PG. 2001. Smoking increases carcinogenic polycyclic aromatic hydrocarbons in human lung tissue. Cancer Res. 61:6367–6371. Corpus ID: 16563553.
   PubMed Web of Science ®Google Scholar
• Griffiths AJF, Gelbart WM, Miller JH, Lewontin RC. 1999. The molecular basis of mutation. In: griffiths AJF ,Miller JH, editors, Modern genetic analysis. New York: W H Freeman.
   Google Scholar
• Gudkov AV, Komarova EA. 2016. p53 and the carcinogenicity of chronic inflammation. Cold Spring Harb Perspect Med. 6(11):a026161. doi: 10.1101/cshperspect.a026161.
   PubMed Web of Science ®Google Scholar
• Hendry LB, Muldoon TG. 1988. Actions of an endogenous antitumorigenic agent on mammary tumor development and modeling analysis of its capacity for interacting with DNA. J Steroid Biochem. 30(1-6):325–328. doi: 10.1016/0022-4731(88)90116-1.
   PubMedGoogle Scholar
• Hilder TA, Hodgkiss JM. 2017. Molecular mechanism of binding between 17β-estradiol and DNA. Comput Struct Biotechnol J. 15:91–97. doi: 10.1016/j.csbj.2016.12.001.
   PubMed Web of Science ®Google Scholar
• Hogan ME, Dattagupta N, Whitlock JP. Jr. 1981. Carcinogen-induced alteration of DNA structure. J Biol Chem. 256(9):4504–4513. doi: 10.1016/s0021-9258(19)69464-0.
   PubMed Web of Science ®Google Scholar
• Horn J, Flesher JW, Lehner AF. 1996. 1-Sulfooxymethylpyrene is an electrophilic mutagen and ultimate carcinogen of 1-methyl- and 1-hydroxymethylpyrene. Biochem Biophys Res Commun. 228(1):105–109. doi: 10.1006/BBRC.1996.1623.
   PubMed Web of Science ®Google Scholar
• Huggins C. 1965. Two principles in endocrine therapy of cancers: hormone deprival and hormone interference. Cancer Res. 25(7):1163–1167.
   PubMedGoogle Scholar
• Huggins C. 1978. Endocrine-induced regression of cancers. Am J Surg. 136(2):233–238. doi: 10.1016/0002-9610(78)90235-0.
   PubMed Web of Science ®Google Scholar
• Huggins C, Pollice L. 1958. Effect of 3-methylcholanthrene on the endocrine system and metabolism of the rat and its influence to retard growth of mammary tumors hitherto refractory. J Exp Med. 107(1):13–32. doi: 10.1084/jem.107.1.13.
   PubMed Web of Science ®Google Scholar
• Huggins C, Yang NC. 1962. Induction and extinction of mammary cancer. Science. 137(3526):257–262. doi: 10.1126/science.137.3526.257.
   PubMed Web of Science ®Google Scholar
• Irobalieva RN, Fogg JM, Dj C, Jr, Sutthibutpong T, Chen M, Barker AK, Ludtke SJ, Harris SA, Schmid MF, Chiu W, et al. 2015. Structural diversity of supercoiled DNA. Nature Comm. 6:1–9. doi: 10.1038/ncomms9440.
   Web of Science ®Google Scholar
• Jameson CW. 2019. Polycyclic aromatic hydrocarbons and associated occupational exposures. In: Baan RA, Stewart BW, Straif K, editors. Tumour Site Concordance and Mechanisms of Carcinogenesis. Lyon (FR): International Agency for Research on Cancer; 2019. (IARC Scientific Publications, No. 165.) Part 1, Concordance between cancer in humans and in experimental animals. Available from: https://www.ncbi.nlm.nih.gov/books/NBK570331.
   Google Scholar
• Jeong HK, Shlyankevich M, Surh YJ. 1995. Intrinsic mutagenicity and electrophilicity of 1-sulfooxy-3-methylcholanthrene: implications for metabolic activation of the carcinogen 3-methylcholanthrene. Biochem Mol Biol Int. 37:885–893. Corpus ID: 34093011.
   PubMedGoogle Scholar
• Jerina DM, Chadha A, Cheh AM, Schurdak ME, Wood AW, Sayer JM. 1991. Covalent bonding of bay-region diol epoxides to nucleic acids. Adv Exp Med Biol. 283:533–553. doi: 10.1007/978-1-4684-5877-0_70.
   PubMedGoogle Scholar
• Jerina DM, Sayer JM, Thakker DR, Yagi H, Levin W, Wood AW, Conney AH. 1980. Carcinogenicity of polycyclic aromatic hydrocarbons: the Bay Region theory. In Pullman B, Ts’o POP, Gelboin H, editors, Carcinogenesis: fundamental mechanisms and environmental effects. Dordrecht, the Netherlands: D Reidel Publishing Co.; p. 1–12. doi: 10.1007/978-94-009-9104-0_1.
   Google Scholar
• Jiang H, Lai Y, Hu K, Chen D, Liu B, Liu Y. 2015. Genotoxicity of 1-methylpyrene and 1-hydroxymethylpyrene in Chinese hamster V79-derived cells expressing both human CYP2E1 and SULT1A1. Environ Mol Mutagen. 56(4):404–411. doi: 10.1002/em.21912.
   PubMed Web of Science ®Google Scholar
• Kaetzel DM, Jr., Maul RS, Liu B, Bonthron D, Fenstermaker RA, Coyne DW. 1994. Platelet-derived growth factor A-chain gene transcription is mediated by positive and negative regulatory regions in the promoter. Biochem J. 301 (Pt 2):321–327. doi: 10.1042/bj3010321.
   PubMed Web of Science ®Google Scholar
• Kim SH, Ganji M, Kim E, van der Torre J, Abbondanzieri E, Dekker C. 2018. DNA sequence encodes the position of DNA supercoils. Elife. 7:e36557. doi: 10.7554/eLife.36557.
   PubMed Web of Science ®Google Scholar
• Kraemer CM. 2017. Vitamin C (Ascorbic acid). Medscape, at https://emedicine.medscape.com/article/2088649-overview., accessed 5/15/20.
   Google Scholar
• Kumar R, Li DQ, Müller S, Knapp S. 2016. Epigenomic regulation of oncogenesis by chromatin remodeling. Oncogene. 35(34):4423–4436. doi: 10.1038/onc.2015.513.
   PubMed Web of Science ®Google Scholar
• Lehner AF, Burzynski SR, Hendry LB. 1986. 3-Phenylacetylamino-2,6-piperidinedione, a naturally-occurring peptide analogue with apparent antineoplastic activity, may bind to DNA. Drugs Exp Clin Res. 12:57–72. Corpus ID: 19484065.
   PubMedGoogle Scholar
• Lehner AF, Burzynski SR, Hendry LB. 1992. Further studies on the specificity of interaction of 3-phenylacetylamino-2,6-piperidinedione with DNA. Intnl J of Exptl Clin Chemotherapy. 5:63–71.
   Google Scholar
• Lehner AF, Horn J, Flesher JW. 1996. Benzylic carbonium ions as ultimate carcinogens of polynuclear aromatic hydrocarbons. J Mol Struct Theochem. 366(3):203–217. doi: 10.1016/0166-1280(96)04562-9.
   Web of Science ®Google Scholar
• Lehner AF, Horn J, Flesher JW. 2002. Mass spectral analysis of unstable N7-aralkyl DNA adducts resulting from reaction of 7-sulfooxymethyl-12-methylbenz[a]anthracene (SMBA) with DNA and deoxynucleotides. Polycyclic Aromat Compd. 22(3-4):415–432. doi: 10.1080/10406630290103636.
   Web of Science ®Google Scholar
• Lehner AF, Horn J, Flesher JW. 2017. One electron oxidation of 3-methylcholanthrene: a chemical model for its mechanism of carcinogenesis. J Mol Struct. 1137:67–83. doi: 10.1016/j.molstruc.2017.01.084.
   Web of Science ®Google Scholar
• Lehner AF, Muldoon TG, Mahesh VB, Bransome ED, Jr, Hendry LB. 1987. Initial studies of a phytoestrogen-deoxyribonucleic acid interaction. Mol Endocrinol. 1(5):377–387. doi: 10.1210/mend-1-5-377.
   PubMedGoogle Scholar
• Lehr RE, Jerina DM. 1977. Relationships of quantum mechanical calculations, relative mutagenicity of benzo[a]anthracene diol epoxides, and “bay region” concept of aromatic hydrocarbon carcinogenicity. J Toxicol Environ Health. 2(6):1259–1265. doi: 10.1080/15287397709529528.
   PubMed Web of Science ®Google Scholar
• Luchnik AN. 2014. DNA conformational transitions induced by supercoiling control transcription in chromatin. Gene Regul Syst Bio. 8:89–96. doi: 10.4137/GRSB.S13756.
   PubMedGoogle Scholar
• MacLeod MC, Tang MS. 1985. Interactions of benzo(a)pyrene diol-epoxides with linear and supercoiled DNA. Cancer Res. 45:51–56. Corpus ID: 22304689.
   PubMed Web of Science ®Google Scholar
• Malarkey DE Hoenerhoff M, Maronpot RR. 2013. Carcinogenesis: mechanisms and manifestations. In: haschek W, Rousseaux C, Wallig M, editors, Haschek and Rousseaux’s handbook of toxicologic pathology, 3rd ed, New York: Elsevier; p. 107–146. doi: 10.1016/B978-0-12-415759-0.00005-4.
   Google Scholar
• Maul RS, Zhang H, Reid IJ, Pedigo NG, Kaetzel DM. 1998. Identification of a cell type-specific enhancer in the distal 5’-region of the platelet-derived growth factor A-chain gene. J Biol Chem. 273(50):33239–33246. doi: 10.1074/JBC.273.50.33239.
   PubMed Web of Science ®Google Scholar
• Miller EC, Miller JA. 1981. Mechanisms of chemical carcinogenesis. Cancer. 47(S5):1055–1064. doi: 10.1002/1097-0142(19810301)47:5+<1055::aid-cncr2820471302>3.0.co;2-3.
   PubMedGoogle Scholar
• Monnerjahn S, Seidel A, Steinberg P, Oesch F, Hinz M, Stezowsky JJ, Hewer A, Phillips DH, Glatt HR. 1993. Formation of DNA adducts from 1-hydroxymethylpyrene in liver cells in vivo and in vitro. IARC Sci Publ. 124(124):189–193. Corpus ID: 36935935.
   Google Scholar
• Myers SR, Flesher JW. 1991a. Bioalkylation of benz[a]anthracene, 7-methylbenz[a]anthracene, and 12-methylbenz[a]anthracene in rat lung cytosol preparations. Biochem Pharmacol. 41(11):1683–1689. doi: 10.1016/0006-2952(91)90170-A.
   PubMed Web of Science ®Google Scholar
• Myers SR, Flesher JW. 1991b. Metabolism of chrysene, 5-methylchrysene, 6-methylchrysene and 5,6-dimethylchrysene in rat liver cytosol, in vitro, and in rat subcutaneous tissue, in vivo. Chem Biol Interact. 77(2):203–221. doi: 10.1016/0009-2797(91)90074-h.
   PubMed Web of Science ®Google Scholar
• Natarajan RK, Flesher JW. 1973. Synthesis and carcinogenicity of compounds related to 6-hydroxymethylbenzo(a)pyrene. J Med Chem. 16(6):714–715. doi: 10.1002/chin.197341240.
   PubMed Web of Science ®Google Scholar
• Nelson SM, Ferguson LR, Denny WA. 2004. DNA and the chromosome – varied targets for chemotherapy. Cell Chromosome. 3(1):2. doi: 10.1186/1475-9268-3-2.
   PubMedGoogle Scholar
• Ramesh A, Kumar A, Aramandla MP, Nyanda AM. 2015. Polycyclic aromatic hydrocarbon residues in serum samples of autopsied individuals from Tennessee. Int J Environ Res Public Health. 12(1):322–334. doi: 10.3390/ijerph120100322.
   Web of Science ®Google Scholar
• Ravi Kumar MN, Vadhanam MV, Horn J, Flesher JW, Gupta RC. 2005. Formation of benzylic-DNA adducts resulting from 7,12-dimethylbenz[a]anthracene in vivo. Chem Res Toxicol. 18(4):686–691. doi: 10.1021/tx049686p.
   PubMed Web of Science ®Google Scholar
• Reymer A, Zakrzewska K, Lavery R. 2018. Sequence-dependent response of DNA to torsional stress: a potential biological regulation mechanism. Nucleic Acids Res. 46(4):1684–1694. doi: 10.1093/nar/gkx1270.
   PubMed Web of Science ®Google Scholar
• Rosemann M, Schulze B, Abel H. 1994. DNA supercoiling and repair in peripheral lymphocytes as a measure of acute radiation response after radiotherapy. Radiat Oncol Investig. 2(3):126–133. doi: 10.1002/ROI.2970020304.
   PubMedGoogle Scholar
• Roy AB. 2020. Sulfation of drugs & related compounds. In Mulder GJ, editor, The chemistry of sulfate esters and related compounds, Chapter 2. Boca Raton, FL: CRC Press; p. 5–30. doi: 10.1201/9780429279911.
   Google Scholar
• Schuster-Böckler B, Lehner B. 2012. Chromatin organization is a major influence on regional mutation rates in human cancer cells. Nature. 488(7412):504–507. doi: 10.1038/nature11273.
   PubMed Web of Science ®Google Scholar
• Scott S, Xu ZM, Kouzine F, Berard DJ, Shaheen C, Gravel B, Saunders L, Hofkirchner A, Leroux C, Laurin J, et al. 2018. Visualizing structure-mediated interactions in supercoiled DNA molecules. Nucleic Acids Res. 46(9):4622–4631. doi: 10.1093/nar/gky266.
   PubMed Web of Science ®Google Scholar
• Searle MS, Maynard AJ, Williams HEL. 2003. DNA recognition by the anthracycline antibiotic Respinomycin D: NMR structure of the intercalation complex with d(AGACGTCT)2. Org Biomol Chem. 1(1):60–66. doi: 10.1039/B208622K.
   PubMed Web of Science ®Google Scholar
• Shen CKJ, Hu WS. 1986. DNA supercoiling of recombinant plasmids in mammalian cells. Proc Natl Acad Sci USA. 83(6):1641–1645. doi: 10.1073/pnas.83.6.1641.
   PubMed Web of Science ®Google Scholar
• Shi X, Mao Y, Knapton AD, Ding M, Rojanasakul Y, Gannett PM, Dalal N, Liu K. 1994. Reaction of Cr(VI) with ascorbate and hydrogen peroxide generates hydroxyl radicals and causes DNA damage: role of a Cr(IV)-mediated Fenton-like reaction. Carcinogenesis. 15(11):2475–2478. doi: 10.1093/carcin/15.11.2475.
   PubMed Web of Science ®Google Scholar
• Sigmon J, Larcom LL. 1996. The effect of ethidium bromide on mobility of DNA fragments in agarose gel electrophoresis. Electrophoresis. 17(10):1524–1527. doi: 10.1002/elps.1150171003.
   PubMed Web of Science ®Google Scholar
• Slaymaker IM, Fu Y, Toso DB, Ranatunga N, Brewster A, Forsburg SL, Zhou ZH, Chen XS. 2013. Mini-chromosome maintenance complexes form a filament to remodel DNA structure and topology. Nucleic Acids Res. 41(5):3446–3456. doi: 10.1093/nar/gkt022.
   PubMed Web of Science ®Google Scholar
• Snyder RD, Holt PA, Maguire JM, Trent JO. 2013. Prediction of noncovalent Drug/DNA interaction using computational docking models: studies with over 1350 launched drugs. Environ Mol Mutagen. 54(8):668–681. doi: 10.1002/em.21796.
   PubMed Web of Science ®Google Scholar
• Stansbury KH, Flesher JW, Gupta RC. 1994. Mechanism of aralkyl-DNA adduct formation from benzo[a]pyrene in vivo. Chem Res Toxicol. 7(2):254–259. doi: 10.1021/TX00038A019.
   PubMed Web of Science ®Google Scholar
• Surh YJ. 2003. Cancer chemoprevention with dietary phytochemicals. Nat Rev Cancer. 3(10):768–780. doi: 10.1038/nrc1189.
   PubMed Web of Science ®Google Scholar
• Surh YJ, Blomquist JC, Miller JA. 1991. Activation of 1-hydroxymethylpyrene to an electrophilic and mutagenic metabolite by rat hepatic sulfotransferase activity. Adv Exp Med Biol. 283:383–391. doi: 10.1016/0006-2952(91)90479-o.
   PubMedGoogle Scholar
• Surh YJ, Liem A, Miller JA, Tannenbaum SR. 1994a. 5-Sulfooxymethylfurfural as a possible ultimate mutagenic and carcinogenic metabolite of the Maillard reaction product, 5-hydroxymethylfurfural. Carcinogenesis. 15(10):2375–2377. doi: 10.1093/carcin/15.10.2375.
   PubMed Web of Science ®Google Scholar
• Surh YJ, Miller JA. 1994. Roles of electrophilic sulfuric acid ester metabolites in mutagenesis and carcinogenesis by some polynuclear aromatic hydrocarbons. Chem Biol Interact. 92(1-3):351–362. doi: 10.1016/0009-2797(94)90076-0.
   PubMed Web of Science ®Google Scholar
• Surh YJ, Park KK, Miller JA. 1994b. Inhibitory effect of vitamin C on the mutagenicity and covalent DNA binding of the electrophilic and carcinogenic metabolite, 6-sulfooxymethylbenzo[a]pyrene. Carcinogenesis. 15(5):917–920. doi: 10.1093/carcin/15.5.917.
   PubMed Web of Science ®Google Scholar
• Surh YJ, Tannenbaum SR. 1994. Activation of the Maillard reaction product 5-(hydroxymethyl)furfural to strong mutagens via allylic sulfonation and chlorination. Chem Res Toxicol. 7(3):313–318. doi: 10.1016/S0009-2797(97)00134-8.
   PubMed Web of Science ®Google Scholar
• Sydnor KL, Bergo CH, Flesher JW. 1980. Effect of various substituents in the 6-position on the relative carcinogenic activity of a series of benzo[a]pyrene derivatives. Chem Biol Interact. 29(2):159–167. doi: 10.1016/0009-2797(80)90030-7.
   PubMed Web of Science ®Google Scholar
• Tang MS, Pfeifer GP, Denissenko MF, Feng Z, Hu W, Pao A, Zheng YI, Zheng JB, Li H, Chen JX. 2002. Mapping polycyclic aromatic hydrocarbon and aromatic amine-induced DNA damage in cancer-related genes at the sequence level. Int J Hyg Environ Health. 205(1-2):103–113. doi: 10.1078/1438-4639-00135.
   PubMed Web of Science ®Google Scholar
• Teves SS, Henikoff S. 2014. DNA torsion as a feedback mediator of transcription and chromatin dynamics. Nucleus. 5(3):211–218. doi: 10.4161/nucl.29086.
   PubMed Web of Science ®Google Scholar
• Trieb M, Rauch C, Wibowo FR, Wellenzohn B, Liedl KR. 2004. Cooperative effects on the formation of intercalation sites. Nucleic Acids Res. 32(15):4696–4703. doi: 10.1093/NAR/GKH788.
   PubMed Web of Science ®Google Scholar
• US Environmental Protection Agency. 1987. Health effects assessment for pyrene. Accessed at https://nepis.epa.gov/Exe/ZyPDF.cgi/2000FDPR.PDF?Dockey=2000FDPR.PDF. June 2, 2022.
   Google Scholar
• Vadhanam MV, Horn J, Flesher JW, Gupta RC. 2003. Detection of benzylic adducts in DNA and nucleotides from 7-sulfooxymethyl-12-methylbenz[a]anthracene and related compounds by 32P-postlabeling using new TLC systems. Chem Biol Interact. 146(1):81–87. doi: 10.1016/S0009-2797(03)00086-3.
   PubMed Web of Science ®Google Scholar
• Vu AT, Taylor KM, Holman MR, Ding YS, Hearn B, Watson CH. 2015. Polycyclic aromatic hydrocarbons in the mainstream smoke of popular U.S. cigarettes. Chem Res Toxicol. 28(8):1616–1626. doi: 10.1021/acs.chemrestox.5b00190.
   PubMed Web of Science ®Google Scholar
• Wang JC, Lynch AS. 1996. Effects of DNA supercoiling on gene expression. In Lin ECC, Lynch AS, editors, Regulation of gene expression in Escherichia coli. Austin: RG Landes Co; p. 127–148. doi: 10.1007/978-1-4684-8601-8.
   Google Scholar
• Wei H, Guangbin L, Yong T, Qin Z. 2015. Emission of polycyclic aromatic hydrocarbons from different types of motor vehicles’ exhaust. Environ Earth Sci. 74(7):5557–5564. doi: 10.1007/s12665-015-4570-9.
   Web of Science ®Google Scholar
• Wolfe A, Shimer GH, Jr., Meehan T. 1987. Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry. 26(20):6392–6396. doi: 10.1021/BI00394A013.
   PubMed Web of Science ®Google Scholar
• Yu S, Wang G, Shi Y, Xu H, Zheng Y, Chen Y. 2020. MCMs in cancer: prognostic potential and mechanisms. Anal Cell Pathol (Amst). 2020:3750211–3750294. 1 doi: 10.1155/2020/3750294.
   Google Scholar
• Zeugin JA, Hartley JL. 1985. Ethanol precipitation of DNA. Focus. 7:1–2.
   Google Scholar