Interactions of bleomycin analogs with deoxyribonucleic acid and metal ions studied by fluorescence quenching

Huang, Chen-Hsiung; Galvan, Louis; Crooke, Stanley T.

doi:10.1021/bi00550a006

Cited by 34 publications

(26 citation statements)

References 25 publications

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“…4 and 5 can be described in terms of four parameters: AZni = 8j(Zn-Bleo-A2) -5i(Bleo-A2), [1] Zni= 5(Zn-B1eo-A2-poly(dA-dT)) -Sj(Bleo-A2-poly(dA-dT)), [2] ANA = 5,(Bleo-A2-poly(dA-dT)) -5i(Bleo-A2), [3] ANA = 5j(Zn-Bleo-A2-poly(dA-dT)) -3j(Zn-Bleo-A2), [4] in which 8i refers to the chemical shift of the ith resonance of the species indicated in parentheses. Clearly, AZn and Az'n reflect the effect ofzinc binding to the free and nucleic acid-bound antibiotics, respectively, and ANA and ANA reflect the effect of nucleic acid binding to the free and zinc-bound antibiotics, respectively.…”

Section: Methodsmentioning

confidence: 99%

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Proton NMR studies of the Zn(II)--bleomycin-A2--poly(dA-dT) ternary complex.

Glickson¹,

Pillai²,

Sakai³

1981

Proc. Natl. Acad. Sci. U.S.A.

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Proton NMR spectra demonstrate the formation of a ternary complex, Zn(H)-bleomycin-Ag-poly(dA-dT), which serves as an analog ofthe putative active complex, Fe(II)-bleomycin-A_-DNA. Here we report a NMR study of Zn(II)-Bleo-A2-poly(dAdT), a diamagnetic and stable analog of the putative active ternary complex. Using chemical shift perturbations that accompany binding of Bleo-A2 to the metal ion and to the nucleic acid, we have identified potential sites of interaction between the metal ion, antibiotic, and nucleic acid. The underlying assumption of this study is that the structure of the Zn(II)-Bleo-A2-poly(dA-dT) complex resembles that of the putative active --~~H 0 OH HO OCN

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Section: Methodsmentioning

confidence: 99%

“…Formation of such ternary complexes is suggested by the quenching of bleomycin fluorescence in the presence of DNA and either Fe(II) (2) or Cu(II) (3). Perturbations of the EPR spectrum demonstrate the formation ofNO-Fe(II)-Bleo-DNA, an inactive analog of the oxygen adduct of the putative active ternary complex (4).…”

mentioning

confidence: 99%

Proton NMR studies of the Zn(II)--bleomycin-A2--poly(dA-dT) ternary complex.

Glickson¹,

Pillai²,

Sakai³

1981

Proc. Natl. Acad. Sci. U.S.A.

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“…The bithiazole moiety is one domain of bleomycin, which was shown to interact with DNA [4,5]. However, the bithiazole ligands are of interest not only to design biological models of BLM [6,7] but also for their extensive applications in material [8,9] and polymer science [10,11].…”

Section: Introductionmentioning

confidence: 99%

Cadmium(II) complexes containing 2,2′-dimethyl-4,4′-bithiazole ligand: synthesis, characterization, and crystal structure

Notash

Safari

Abedi

et al. 2009

Journal of Coordination Chemistry

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Mononuclear and coordination polymer compounds of 2,2 0 -dimethyl-4,4 0 -bithiazole (dm4bt) ligand have been prepared by metallation of dm4bt with Cd(NO 3 ) 2 Á 4H 2 O and CdCl 2 Á H 2 O. The compounds were characterized by IR, 1 H NMR, UV-Vis spectroscopy, and X-ray crystallography. The structural study of [Cd(dm4bt) 2 (NO 3 ) 2 ] Á H 2 O (1) shows that the complex is a monomeric seven-coordinate (CdN 4 O 3 ) cadmium(II)-bithiazole system with two bidentate dm4bt and mono and bidentate nitrates. The structure of [Cd(dm4bt)Cl 2 ] n (2) is a distorted octahedral environment around the cadmium(II) (CdN 2 Cl 4 ) forming a 1-D coordination polymer as a result of bridging by two chlorides and 2-D structure from -stacking interactions.

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“…The metal interactions with bleomycin and 1 ,l@phenanthroline have been studied extensively. Both drugs bind to and break DNA (Haidle, 1971;Strong & Crooke, 1978;Huang et al, 1980Huang et al, , 1981Mirabelli et al, , 1980Marshall et al, 1981). Their DNA-degrading reaction exhibits an oxygen requirement (Sausville et al, 1976(Sausville et al, , 1978aSigman et al, 1979) and can be terminated by metal chelating agents such as EDTA.…”

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confidence: 99%

“…The available evidence supports the concept that bleomycin exhibits its DNA-cutting activity through the formation of a complex of DNA-bleomycinqchelated Fe-(II).molecular oxygen. Oxidation of the bound Fe(I1) ion occurs in this complex with concomitant reduction of oxygen to produce oxygen free radicals (Povirk et al, 1979;Huang et al, 1980;Suguira, 1980). Studies on the DNA cleavage induced by 1,lO-phenanthroline in the presence of a reducing agent suggest that this drug complexes with Cu(I1) and the (1 ,10-phenanthroline)2Cu+ complex may bind to DNA.…”

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confidence: 99%

The mechanism of deoxyribonucleic acid breakage induced by 4'-(9-acridinylamino)methanesulfon-m-anisidine and copper: role for cuprous ion and oxygen free radicals

Wong¹,

Huang²,

Crooke³

1984

Biochemistry

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4'-(9-Acridinylamino)methanesulfon-m-anisidide (mAMSA) interacts with Cu(II) ion, as indicated by changes in the mAMSA absorption spectrum induced by Cu(II). The spectral changes are due to the oxidation of mAMSA by Cu(II), resulting in an oxidized mAMSA product and Cu(I). Two lines of evidence for the oxidation of mAMSA are as follows: (1) The spectral changes induced by manganese oxide, an oxidizing agent, were similar to those induced by Cu(II), and (2) the Cu(II)-induced spectral changes were reversed by a reducing agent, NADPH. Thin-layer chromatographic studies showed the oxidized mAMSA product to be N1-methylsulfonyl-N4-(9-acridinyl)-3-methoxy-2,5-cyclohexadiene-1, 4-diimine (mAQDI). The involvement of Cu(I) in the reaction was demonstrated by the use of two Cu(I)-specific chelating agents, neocuproine and bathocuproine. Neocuproine or bathocuproine chelated the Cu(I) ions in the mixture, producing Cu(neocuproine)2+ complex or Cu(bathocuproine)2+ complex. The stoichiometry of mAMSA-Cu(II) interactions was determined by titrating the mAMSA-Cu(II) mixtures with bathocuproine. Job plots of the absorbance at 480 nm showed a clear end point at a Cu(II)/mAMSA ratio of 1.5/1, indicating that 1.5 equiv of Cu(II) reacts with 1 equiv of mAMSA to produce 1.5 equiv of Cu(I). Cu(I) plays an important role in the mAMSA-Cu(II)-induced DNA breakage, since in the presence of neocuproine the DNA breakage is inhibited. Up to 200 microM, Cu(I) by itself is virtually ineffective, in contrast to the mixture of mAMSA and Cu(II).(ABSTRACT TRUNCATED AT 250 WORDS)

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Interactions of bleomycin analogs with deoxyribonucleic acid and metal ions studied by fluorescence quenching

Cited by 34 publications

References 25 publications

Proton NMR studies of the Zn(II)--bleomycin-A2--poly(dA-dT) ternary complex.

Proton NMR studies of the Zn(II)--bleomycin-A2--poly(dA-dT) ternary complex.

Cadmium(II) complexes containing 2,2′-dimethyl-4,4′-bithiazole ligand: synthesis, characterization, and crystal structure

The mechanism of deoxyribonucleic acid breakage induced by 4'-(9-acridinylamino)methanesulfon-m-anisidine and copper: role for cuprous ion and oxygen free radicals

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