Clerocidin alkylates DNA through its epoxide function: Evidence for a fine tuned mechanism of action

Nucleic Acids Research

Volumn 31, Issue 17, 2003, Pages 5149-5156

  Richter, Sara ^c   Gatto, Barbara ^c   Fabris, Daniele ^a   Takao, Ken Ichi ^b   Kobayashi, Susumu ^b   Palumbo, Manlio ^c  

^a UNIVERSITY OF MARYLAND   (United States)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

^c UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CLEROCIDIN DERIVATIVE; DEOXYGUANOSINE; DNA TOPOISOMERASE (ATP HYDROLYSING); DOUBLE STRANDED DNA; EPOXIDE; ETHYLENE OXIDE; GUANINE; GYRASE INHIBITOR; NUCLEIC ACID; PENTOSE; PLASMID DNA; PURINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DNA ADDUCT; DNA ALKYLATION; DNA MODIFICATION; DNA STRAND BREAKAGE; DRUG ACTIVITY; DRUG STRUCTURE; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; PRIORITY JOURNAL;

ALKYLATING AGENTS; ALKYLATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DITERPENES; DNA; DNA ADDUCTS; DNA DAMAGE; DNA, SINGLE-STRANDED; EPOXY COMPOUNDS; GUANINE; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PLASMIDS;

EID: 0344443399     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/gkg696     Document Type: Article

References (29)

1. Binaschi, M., Zagotto, G., Palumbo, M., Zunino, F., Farinosi, R. and Capranico, G. (1997) Irreversible and reversible topoisomerase II DNA cleavage stimulated by clerocidin: sequence specificity and structural drug determinants. Cancer Res., 57, 1710-1716.
2. Gatto, B., Richter, S., Moro, S., Capranico, G. and Palumbo, M. (2001) The topoisomerase II poison clerocidin alkylates non-paired guanines of DNA: implications for irreversible stimulation of DNA cleavage. Nucleic Acids Res., 29, 4224-4230.
3. Kawada, S., Yamashita, Y., Fujii, N. and Nakano, H. (1991) Induction of a heat-stable topoisomerase II-DNA cleavable complex by nonintercalative terpenoides, terpentecin and clerocidin. Cancer Res., 51, 2922-2925.
4. Kawada, S.Z., Yamashita, Y., Uosaki, Y., Gomi, K., Iwasaki, T., Takiguchi, T. and Nakano, H. (1992) UCT4B, a new antitumor antibiotic with topoisomerase II mediated DNA cleavage activity, from Streptomyces sp. J. Antibiot. Tokyo, 45, 1182-1184.
5. Kawada, S., Yamashita, Y., Ochiai, K., Ando, K., Iwasaki, T., Takiguchi, T. and Nakano, H. (1995) Terpentecin and UCT4B, new family of topoisomerase II targeting antitumor antibiotics produced by Streptomyces: producing organism, fermentation and large scale purification. J. Antibiot. Tokyo, 48, 211-216.
6. Hansen, M., Lee, S.-J., Cassady, J. and Hurley, L. (1996) Molecular details of the structure of a psorospermin-DNA covalent/intercalation complex and associated DNA sequence selectivity. J. Am. Chem. Soc., 118, 5553-5561.
7. Hansen, M. and Hurley, L. (1995) Altromycin B threads the DNA helix interacting with both the major and the minor grooves to position itself for site-directed alkylation of guanine N7. J. Am. Chem. Soc., 117, 2421-2429.
8. Gopalakrishnan, S., Harris, T.M. and Stone, M.P. (1990) Intercalation of aflatoxin B1 in two oligodeoxynucleotide adducts: comparative 1H NMR analysis of d(ATCAFBGAT)d(ATCGAT) and d(ATAFBGCAT)2. Biochemistry, 29, 10438-10448.
9. Giri, I., Jenkins, M.D., Schnetz-Boutaud, N.C. and Stone, M.P. (2002) Structural refinement of the 8,9-dihydro-8-(N7-guanyl)-9-hydroxy-aflatoxin B(1) adduct in a 5′-Cp(AFB)G-3′ sequence. Chem. Res. Toxicol., 15, 638-647.
10. Jones, W.R., Johnston, D.S. and Stone, M.P. (1999) Site-specific synthesis of aflatoxin B(1) adducts within an oligodeoxyribonucleotide containing the human p53 codon 249 sequence. Chem. Res. Toxicol., 12, 707-714.
11. Nakajima, N., Okazaki, T., Iwado, S., Kinoshita, T. and Haneishi, T. (1989) New diterpenoid antibiotics, Spirocardins A and B. J. Antibiot. Tokyo, 42, 1741-1748.
12. Takao, K., Aiba, Y., Ito, H. and Kobayashi, S. (1996) Synthetic study on antitumor antibiotic terpentecin: construction of the carbobicyclic decalin moiety. Chem. Lett., 11, 931-932.
13. Takao, K. and Kobayashi, S. (1997) Synthetic study on antitumor antibiotic terpentecin: construction of the carbobicyclic decalin moiety. Tetrahedron Lett., 38, 6685-6688.
14. Wang, J.C. (1974) Interactions between twisted DNAs and enzymes. The effects of superhelical turns. J. Mol. Biol., 87, 797-816.
15. Maxam, A.M. and Gilbert, W. (1980) Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol., 65, 499-560.
16. Andersen, N.R., Lorck, H.O. and Rasmussen, P.R. (1983) Fermentation, isolation and characterization of antibiotic PR-1350. J. Antibiot. Tokyo, 36, 753-760.
17. Andersen, N. and Rasmussen, P. (1984) The costitution of Clerocidin. A new antibiotic isolated from Oidiodendron truncatum. Tetrahedron Lett., 25, 465-468.
18. Andersen, N., Lork, H. and Rassmussen, P. (1984) The relative and absolute configuration of clerocidin and its cometabolites. Tetrahedron Lett., 25, 469-472.
19. Prakash, A., Tran, H.-P., Peng, C., Koyalamudi, S. and Dameron, C. (2000) Kinetics of DNA alkylation, depurination and hydrolysis of anti diol epoxide of benzo(a)pyrene and the effect of cadmium on DNA alkylation. Chem. Biol. Interact., 125, 133-150.
20. Neagu, I., Koivisto, P., Neagu, C., Kostiainen, R., Stenby, K. and Peltonen, K. (1995) Butadiene monoxide and deoxyguanosine alkylation products at the N7-position. Carcinogenesis, 16, 1809-1813.
21. Kochetkov, N.K. and Budowskii, E.I. (1972) Organic Chemistry of Nucleic Acids. Plenum, New York, NY.
22. Beck, J.L., Colgrave, M.L., Ralph, S.F. and Sheil, M.M. (2001) Electrospray ionization mass spectrometry of oligonucleotide complexes with drugs, metals and proteins. Mass Spectrom. Rev., 20, 61-87.
23. Zhang, Q., Ding, Z., Creighton, D.J., Ganem, B. and Fabris, D. (2002) Alkylation of nucleic acids by the antitumor agent COMC. Org. Lett., 4, 1459-1462.
24. Comisarow, M.B. and Marshall, A.G. (1974) Fourier transform ion cyclotron resonance. Chem. Phys. Lett., 25, 282-283.
25. Marshall, A.G., Hendrickson, C.L. and Jackson, G.S. (1998) Fourier transform ion cyclotron resonance mass spectrometry: a primer. Mass Spectrom. Rev., 17, 1-35.
26. Boogaard, P.J., van Sittert, N.J., Watson, W.P. and de Kloe, K.P. (2001) A novel DNA adduct, originating from 1,2-epoxy-3,4-butanediol, is the major DNA adduct after exposure to [2,3-(14)C]-1,3-butadiene,[4-(14)C]-1,2-epoxy-3-butane. Chem. Biol. Interact., 135-136, 687-693.
27. Koivisto, P. and Peltonen, K. (2001) N7-guanine adducts of the epoxy metabolites of 1,3-butadiene in mice lung. Chem. Biol. Interact., 135-136, 363-372.
28. Koivisto, P., Kilpelainen, I., Rasanen, I., Adler, I.D., Pacchierotti, F. and Peltonen, K. (1999) Butadiene diolepoxide- and diepoxybutane-derived DNA adducts at N7-guanine: a high occurrence of diolepoxide-derived adducts in mouse lung after 1,3-butadiene exposure. Carcinogenesis, 20, 1253-1259.
29. Hara, M., Yoshida, M. and Nakamo, H. (1990) Covalent modification and single-strand scission of DNA by a new antitumor antibiotic Kapurimycin A3. Biochemistry, 29, 10449-10455.