Abstract:
:A method for the preparation of biologically active [3H]- and [13C]bleomycin A2 is described. Demethyl Cu(II):bleomycin A2, isolated after pyrolysis of Cu(II):bleomycin A2, was methylated with either [3H]-or [13C]methyl iodide, which resulted in Cu(II):bleomycin A2 labeled in the dimethylsulfonium moiety. Copper was removed by treatment with dithizone in chloroform, and structures were verified by thin-layer chromatography and 1H and 13C nuclear magnetic resonance spectroscopy. Copper-free [3H]-and [13C]bleomycin A2 are active in the degradation of DNA in vitro. Gel exclusion chromatograhy and equilibrium dialysis were used to determine the apparent equilibrium constants for binding of [3H]bleomycin A2 and Cu(II):[3H]bleomycin A2 to calf thymus DNA, noncovalently associated polydeoxyguanylate:polydeoxycytidylate, and noncovalently associated polydeoxyadenylate:polydeoxythymidylate. In 2.5 mM sodium phosphate buffer, pH 7.0, binding data obtained by gel filtration with calf thymus DNA reveal an apparent equilibrium constant for [3H]bleomycin A2 of 5.7 X 10(5)/mol and for Cu(II):[3H]bleomycin A2 of 3.9 X 10(5)/mol. One molecule of [3H]bleomycin A2 binds for every 3.7 base pairs in DNA, and one molecule of Cu(II):[3H]bleomycin A2 binds for every 2.8 base pairs in DNA. Analysis of binding data with calf thymus DNA, noncovalently associated polydeoxyguanylate:polydeoxycytidylate, and noncovalently associated polydeoxyadenylate:polydeoxythymidylate obtained by equilibrium dialysis reveals, in each instance, 2 types of binding sites for both the copper and metal-free form of the antibiotic. For those sites in calf thymus DNA with tighter binding affinity, the apparent equilibrium constant for [3H]bleomycin A2 was 6.8 X 10(5)/mol and for the Cu(II):[3H]bleomycin A2 complex, 4.4 X 10(5)/mol. As seen with calf thymus DNA, the affinity of [3H]bleomycin A2 is slightly greater than that of Cu(II):[3H]bleomycin A2 for the synthetic DNAs, although more of the copper form of the drug binds to these polymers.
journal_name
Cancer Resjournal_title
Cancer researchauthors
Roy SN,Orr GA,Brewer CF,Horwitz SBsubject
Has Abstractpub_date
1981-11-01 00:00:00pages
4471-7issue
11 Pt 1eissn
0008-5472issn
1538-7445journal_volume
41pub_type
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