Studies of complex formation of olivomycin A and its derivatives with DNA

Andreeva, E. V.; Vinogradov, A.; Tevyashova, Anna N.; Olsufyeva, Eugenia N.; Burova, Tatiana V.; Grinberg, Natalia V.; Grinberg, V. Ya.; Skuridin, S. G.; Preobrazhenskaya, M. N.; Shtil, Alexander A.; Кузьмин, В. А.

doi:10.1134/s1607672910060141

Cited by 5 publications

(4 citation statements)

References 12 publications

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“…Studies by other researchers and us 7,14,20 have shown that the formation of complexes of chromomycin A 3 , mithramycin and 1 with DNA induced changes in CD spectra. Importantly, a correlation between the intensity of the induced CD spectra of drug-DNA complexes and the structure of the drug has been demonstrated.…”

Section: ' A4 E4mentioning

confidence: 93%

“…Importantly, a correlation between the intensity of the induced CD spectra of drug-DNA complexes and the structure of the drug has been demonstrated. 14 The effects of the induced CD of the drug-DNA complexes are determined by the interaction of the ligand molecules with the DNA minor groove. Accordingly, the magnitude of induced CD spectra should increase with the enhancement of drug-DNA interaction.…”

Section: ' A4 E4mentioning

confidence: 99%

“…Given that (1) the abilities of 1-5 to form complexes with dsDNA varied dramatically (see above), and (2) the antitumor properties of 1 have been mechanistically attributed to the formation of complexes with DNA; 14 it is plausible to expect that 1-5 exert differential effects on the two parameters related to the antitumor drug potential, that is, an attenuation of topo I-mediated unwinding of supercoiled DNA 20 and the cytotoxic potency for the human HCT116 colon carcinoma cell line. 16 Data in Figure 6 showed almost complete inhibition of plasmid relaxation at 1 mM of 1 (rendered as þ þ þ in Table 2), partial inhibition at 10 mM of 2 and complete inhibition at 10 mM of 3 ( þ and þ þ in Table 2, respectively).…”

Section: ' A4 E4mentioning

confidence: 99%

“…It has been shown that the structure of the sugar moieties in the saccharides is a major factor of 1-DNA complex formation, as the latter parameter has been directly attributed to the cytotoxicity of 1. 14 In the present study, we elucidated the role of the acyl substituents in sugar moieties in anticancer properties of 1, namely, the drug-DNA complex formation, the interference with the catalytic function of the DNA-dependent enzyme topoisomerase I (topo I) and the cytotoxicity for cultured human tumor cells. To this aim we considered three natural aureolic acid antibiotics: olivomycin A (1), olivomycin C (2) and olivomycin B (3), 15 and elaborated the methods of selective hydrolysis of E4-isobutyryl group of olivomycins (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Role of the acyl groups in carbohydrate chains in cytotoxic properties of olivomycin A

et al. 2013

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A series of olivomycin A derivatives containing different combinations of the acyl residues in the carbohydrate chains was obtained. The formation of complexes of Mg(2+)-coordinated dimers of these compounds with double-stranded DNA was studied using spectral methods such as absorption, fluorescence and circular dichroism (CD) spectral analyses. There was a good correlation of the values of binding constants of complexes (antibiotic)2Mg(2+)-DNA, the quantum yields of fluorescence and changes of the induced CD spectra with topoisomerase I inhibition and cytotoxicity. We demonstrate that the presence of the acyl groups in the saccharide residues of olivomycin A derivatives is absolutely necessary for a high cytotoxic potency of these antibiotics. On the basis of the experimental results and quantum chemical calculations, we presume that the acyl residue in the 4-O-position in the A-sugar residue is involved, to the most part, in the antibiotic-antibiotic interactions in the (olivomycin)2Mg(2+) dimers, whereas the O-acyl group in E-olivomicose residue largely participates in the formation of the (olivomycin)2Mg(2+)-DNA complexes.

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Section: ' A4 E4mentioning

confidence: 93%

Section: ' A4 E4mentioning

confidence: 99%

Section: ' A4 E4mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Role of the acyl groups in carbohydrate chains in cytotoxic properties of olivomycin A

et al. 2013

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Modification of olivomycin A at the side chain of the aglycon yields the derivative with perspective antitumor characteristics

Tevyashova

Shtil

Olsufyeva

et al. 2011

Bioorganic & Medicinal Chemistry

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Main trends in the design of semi-synthetic antibiotics of a new generation

Olsufyeva¹,

Yankovskaya²

2020

Russ. Chem. Rev.

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This review summarizes main advances achieved by Russian researchers in the synthesis and characterization of semi-synthetic antibiotics of a new generation in the period from 2004 to 2019. The following classes of compounds are considered as the basis for modification: polycyclic antibacterial glycopeptides of the vancomycin group, classical macrolides, antifungal polyene macrolides, the antitumour antibiotic olivomycin A, antitumour anthracyclines and broad-spectrum antibiotics, in particular, oligomycin A, heliomycin and some other. Main trends in the design of modern anti-infective and antitumour agents over this period are considered in relation to original natural antibiotics, which have been independently discovered by Russian researchers. It is shown that a new type of hybrid structures can, in principle, be synthesized based on glycopeptides, macrolides and other antibiotics, including heterodimers containing a new benzoxaborole pharmacophore. The review addresses the influence of the length of the spacer between two antibiotic molecules on the biological activity of hybrid structures. A combination of genetic engineering techniques and methods of organic synthesis is shown to be useful for the design of new potent antifungal antibiotics based on polyenes of the amphotericin B group. Many new semi-synthetic analogues exhibit important biological properties, such as a broad spectrum of activity and low toxicity. Emphasis is given to certain aspects related to investigation of a broad range of biological activity and mechanisms of action of new derivatives. The bibliography includes 101 references.

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Studies of complex formation of olivomycin A and its derivatives with DNA

Cited by 5 publications

References 12 publications

Role of the acyl groups in carbohydrate chains in cytotoxic properties of olivomycin A

Role of the acyl groups in carbohydrate chains in cytotoxic properties of olivomycin A

Modification of olivomycin A at the side chain of the aglycon yields the derivative with perspective antitumor characteristics

Main trends in the design of semi-synthetic antibiotics of a new generation

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