Monafunctional adenine N-3 adducts of melphalan: Occurrence at a mutational hotspot sequence and resistance to removal by AlkA protein

Environmental and Molecular Mutagenesis

Volumn 31, Issue 4, 1998, Pages 333-339

  Charles, Kwabena ^a   Bauer, Gwen B ^a   Povirk, Lawrence F ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Bifunctional alkylators; Glycosylase; Melphalan; Nitrogen mustards

Indexed keywords

ADENINE; ALKYLATING AGENT; BACTERIAL PROTEIN; CHLORAMBUCIL; CHLORMETHINE DERIVATIVE; MELPHALAN; OXIDOREDUCTASE; RUBREDOXIN NAD+ REDUCTASE; RUBREDOXIN-NAD+ REDUCTASE;

ARTICLE; BACTERIAL GENE; CHEMICAL CARCINOGENESIS; DNA DAMAGE; DNA STRAND BREAKAGE; DRUG DNA BINDING; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SHUTTLE VECTOR; DNA ADDUCT; ENZYMOLOGY; METABOLISM; MUTATION; NUCLEOTIDE SEQUENCE;

BACTERIA (MICROORGANISMS); BRASSICACEAE; ESCHERICHIA COLI;

BASE SEQUENCE; DNA ADDUCTS; ESCHERICHIA COLI; MELPHALAN; MUTATION; NADH, NADPH OXIDOREDUCTASES;

EID: 0031595823     PISSN: 08936692     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2280(1998)31:4<333::AID-EM5>3.0.CO;2-J     Document Type: Article

References (23)

1. Austin MJF, Han Y-H, Povirk LF (1992): DNA sequence analysis of mutations induced by melphalan in the CHO aprt locus. Cancer Genet Cytogenet 64:69-74.
2. Bonodonna G, Valagussa P, Santoro A, Viviani S. Bonfante V, Banfi A (1989): Hodgkin's disease: The Milan Cancer Institute experience with MOPP and ABVD. Recent Results Cancer Res 117:169-174.
3. Carter CA, Habraken Y. Ludlum DB (1988): Release of 7-alkylguanines from haloethylnitrosourea-treated DNA by E. coli 3-methyladenine-DNA glycosylase II. Biochem Biophys Res Commun 155:1261-1265.
4. Chakravarti D, Ibeanu GC, Tano K, Mitra S (1991): Cloning and expression in Escherichia coli of a human cDNA encoding the DNA repair protein N-methylpurine-DNA glycosylase. J Biol Chem 266:15710-15715.
5. Chaudhuri I. Essigmann JM ( 1991 ): 3-Methyladenine mutagenesis under conditions of SOS induction in Escherichia coli. Carcinogenesis 12:2283-2289.
6. Engelward BP, Boosalis MS. Chen BJ, Deng Z, Siciliano MJ. Samson LD (1993): Cloning and characterization of a mouse 3-methylad-enine/7-methylguanine DNA glycosylase cDNA whose gene maps to chromosome 11. Carcinogenesis 14:175-181.
7. Han Y-H, Austin MJF, Pommier Y, Povirk LF (1993): Small deletion and insertion mutations induced by the topoisomerase II inhibitor teniposide in CHO cells and comparison with sites of drugstimulated DNA cleavage in vitro. J Mol Biol 229:52-66.
8. Henne T, Schmähl D (1985): Occurrence of second primary malignancies in man - a second outlook. Cancer Treat Rev 12:77-94.
9. IARC (1981): IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 26: Some Antineoplastic and Immunosuppressive Agents. Lyon, France: International Agency for Research on Cancer, pp 203-215.
10. Karran P, Lindahl T (1985): Cellular defence mechanisms against alkylating agents. Cancer Surv 4:583-599.
11. Loeb LA (1985): Apurinic sites as mutagenic intermediates. Cell 40:483-484.
12. Mattes WB, Lee CS, Laval J, O'Connor TR (1996): Excision of DNA adducts of nitrogen mustards by bacterial and mammalian 3-methyladenine-DNA glycosylases. Carcinogenesis 17:643-648.
13. Nowell PC (1982): Cytogenetics of preleukemia. Cancer Genet Cytogenet 5:265-278.
14. O'Connor TR, Laval F (1990): Isolation and structure of a cDNA expressing a mammalian 3-methyladenine-DNA glycosylase. EMBO J 9:3337-3342.
15. Osborne MR, Lawley PD (1993): Alkylation of DNA by melphalan with special reference to adenine derivatives and adenine-guanine cross-linking. Chem Biol Interact 89:49-60.
16. Osborne MR, Wilman DEV. Lawley PD (1995): Alkylation of DNA by the nitrogen mustard bis(2-chloroethyl)methylamine. Chem Res Toxicol 8:316-320.
17. Pieper RO, Erickson LC (1990): DNA adenine adducts induced by nitrogen mustards and their role in transcription termination in vitro. Carcinogenesis 11:1739-1746.
18. Povirk LF, Shuker DE (1994): DNA damage and mutagenesis induced by nitrogen mustards. Mutat Res 318:205-226.
19. Singer B (1975): The chemical effects of nucleic acid alkylation and their relation to mutagenesis and carcinogenesis. Prog Nucleic Acids Res Mol Biol 15:219-285.
20. Wang P, Bennett RAO. Povirk LF (1990): Melphalan-induced mutagenesis in an SV40-based shuttle vector: Predominance of AT to TA transversions. Cancer Res 50:7527-7531.
21. Wang P, Bauer GB, Bennett RAO. Povirk LF (1991): Thermolabile adenine adducts and AT base pair substitutions induced by nitrogen mustard analogues in an SV40-based shuttle vector. Biochemistry 30:11515-11521.
22. Wang P, Bauer GB, Kellogg GE, Abraham DJ, Povirk LF (1994): Effect of distamycin on chlorambucil-induced mutagenesis in shuttle vector pZ189: Evidence of a role for minor groove binding at adenine N-3. Mutagenesis 9:133-139.
23. Yamada M, Sofuni T, Nohrai T (1992): Preferential induction of ATTA transversion, but not deletions, by chlorambucil at the hisG428 site of Salmonella typhimurium TA102. Mutat Res 283:29-33.