Mitomycin C: small, fast and deadly (but very selective)

Szybalski, 1964, Crosslinking of DNA by enzymatic or activated mitomycins and porfiromycins, bifunctionally‘alkylating’ antibiotics, 23, 946

Armstrong, 1992, Novel interstrand crosslinks induced by the antitumor antibiotic carzinophillin/azinomycin B, J. Am. Chem. Soc., 114, 3144, 10.1021/ja00034a074

Moore, 1977, Bioactivation as a model for drug design. Bioreductive alkylation, Science, 197, 527, 10.1126/science.877572

Tomasz, 1981, Reductive metabolism and alkylation activity of mitomycin C induced by rat liver microsomes, Biochemistry, 20, 5056, 10.1021/bi00520a036

Kohn, 1983, Studies concerning the mechanism of electrophilic substitution reactions of mitomycin C, J. Am. Chem. Soc., 105, 4105, 10.1021/ja00350a067

Danishefsky, 1986, On the characterization of intermediates in the mitomycin activation cascade: a practical synthesis of an aziridinomitosene, J. Am. Chem. Soc., 106, 6424, 10.1021/ja00333a056

Tomasz, 1987, Isolation and structure of a covalent crosslink adduct between mitomycin C and DNA, Science, 235, 1204, 10.1126/science.3103215

Sartorelli, 1994, Mitomycin C: a prototype bioreductive agent, Oncol. Res., 6, 501

Semmelhack, 1990, Bioreductive alkylation as a trigger for toxic effects of dynemicin, Tetrahedron Lett., 31, 1521, 10.1016/0040-4039(90)80005-7

Brown, 1993, SR 4233 (Tirapazamine): a new anticancer drug exploiting hypoxia in solid tumors, Br. J. Cancer, 67, 1163, 10.1038/bjc.1993.220

Tomasz, 1986, Reaction of DNA with chemically or enzymatically activated mitomycin C: isolation and structure of the major covalent adduct, 83, 6702

Bizanek, 1992, Isolation and structure of an intrastrand crosslink adduct of mitomycin C and DNA, Biochemistry, 31, 3084, 10.1021/bi00127a008

Tomasz, 1988, Isolation and characterization of a major adduct between mitomycin C and DNA, J. Am. Chem. Soc., 110, 5892, 10.1021/ja00225a048

Bizanek, 1993, Adducts of mitomycin C and DNA in EMT6 mouse mammary tumor cells: effects of hypoxia and dicumarol on adduct patterns, Cancer Res., 53, 5127

Verdine, 1986, Binding of mitomycin C to a dinucleoside phosphate and DNA

Remers, 1988, Conformations of complexes between mitomycins and decanucleotides. 3. Sequence specificity, binding at C-10, and mitomycin analogs, J. Med. Chem., 31, 1612, 10.1021/jm00403a021

Arora, 1990, Structural, conformational and theoretical binding studies of antitumor antibiotic porfiromycin, a covalent binder of DNA, by X-ray, NMR, and molecular mechanics, J. Med. Chem., 33, 3000, 10.1021/jm00173a014

Norman, 1990, NMR and computational characterization of mitomycin crosslinked to adjacent deoxyguanosines in the minor groove of the d(T-A-C-G-T-A).d(T AC-G-TA) duplex, Biochemistry, 29, 2861, 10.1021/bi00463a032

Sastry, 1995, Solution structure of the monoalkylated mitomycin C-DNA complex, J. Mol. Biol., 247, 338, 10.1006/jmbi.1994.0143

Li, 1991, Studies on the bonding specificity for mitomycin C-DNA monoalkylation processes, J. Am. Chem. Soc., 113, 275, 10.1021/ja00001a040

Kumar, 1992, Recognition of specific DNA sequences by mitomycin C for alkylation, Biochemistry, 31, 1399, 10.1021/bi00120a016

Teng, 1989, DNA sequence specificity of mitomycin crosslinking, Biochemistry, 28, 3901, 10.1021/bi00435a041

Millard, 1990, Determination of the DNA crosslinking sequence specificity of reductively activated mitomycin C at single nucleotide resolution: deoxyguanosine residues at CpG are crosslinked preferentially, J. Am. Chem. Soc., 112, 3637, 10.1021/ja00165a059

Borowy-Borowski, 1990, Recognition between mitomycin C and specific DNA sequences for crosslink formation, Biochemistry, 29, 2999, 10.1021/bi00464a016

Kohn, 1992, On the origins of the DNA sequence selectivity of mitomycin monoalkylation transformations, J. Am. Chem. Soc., 114, 9218, 10.1021/ja00049a082

Suresh Kumar, 1995, Binding of 2,7-diaminomitosene to DNA: model for the precovalent recognition of DNA by activated mitomycin C, Biochemistry, 34, 2662, 10.1021/bi00008a033

Gargiulo, 1995, Alkylation and cross-linking of DNA by the unnatural enantiomer of mitomycin C: mechanism of the DNA-sequence specificity of mitomycins, J. Am. Chem. Soc, 10.1021/ja00142a002

Tomasz, 1987, Reaction of acid-activated mitomycin C with calf thymus DNA and model guanines. Elucidation of the base-catalyzed degra dation of N7-alkylguanine nucleosides, Biochemistry, 26, 2010, 10.1021/bi00381a034

Hopkins, 1991, Sequence preferences of DNA interstrand crosslinking agents: importance of minimal DNA structural reorganization in the crosslinking reactions of mechlorethamine, cisplatin and mitomycin C, Tetrahedron, 47, 2475, 10.1016/S0040-4020(01)81782-8

Alley, 1994, DNA interstrand crosslinking by 2,5-bis1-aziridinyl)-1,4-benzoquinone: nucleotide sequence preferences and covalent structure of the dG-to-dG crosslinks at 5′-d(GNnC) in synthetic oligonucleotide duplexes, J. Am. Chem. Soc., 116, 2734, 10.1021/ja00086a006