Modification of the antibiotic olivomycin I at the 2′-keto group of the side chain. Novel derivatives, antitumor and topoisomerase I-poisoning activity

Tevyashova, Anna N.; Zbarsky, Eugenia N; Balzarini, Jan; Shtil, Alexander A.; Dezhenkova, Lyubov G.; Бухман, В. М.; Zbarsky, Victor B; Preobrazhenskaya, M. N.

doi:10.1038/ja.2008.7

Cited by 17 publications

(11 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%

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%

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

et al. 2013

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“…8) may even have potential usefulness as anti-hepatitis C virus agents. 193 In the mean time, novel derivatives of the antibiotic olivomycin 194,195 and novel anthracene-9,10-diones 196 were reported, although they were considered only as cytostatic, and, regretfully, not as (potential) antiviral agents.…”

Section: H Glycopeptide (And Other) Antibiotic Derivatives: An As Yementioning

confidence: 99%

The next ten stories on antiviral drug discovery (part E): advents, advances, and adventures

Clercq¹

2010

Medicinal Research Reviews

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This review article presents the fifth part (part E) in the series of stories on antiviral drug discovery. The ten stories belonging to this fifth part are dealing with (i) aurintricarboxylic acid; (ii) alkenyldiarylmethanes; (iii) human immunodeficiency virus (HIV) integrase inhibitors; (iv) lens epithelium-derived growth factor as a potential target for HIV proviral DNA integration; (v) the status presens of neuraminidase inhibitors NAIs in the control of influenza virus infections; (vi) the status presens on respiratory syncytial virus inhibitors; (vii) tricyclic (1,N-2-ethenoguanine)-based acyclovir and ganciclovir derivatives; (viii) glycopeptide antibiotics as antivirals targeted at viral entry; (ix) the potential (off-label) use of cidofovir in the treatment of polyoma (JC and BK) virus infections; and (x) finally, thymidine phosphorylase as a target for both antiviral and anticancer agents.

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“…Ïåðâîå íàïðàâëåíèå (ðèñ. 2, íàïðàâëåíèå 1) îñíîâàíî íà ïîëó÷åíèè îêñèìà ïî 2¢-êåòîãðóïïå áîêîâîé öåïè âçàèìîäåéñòâèåì îëèâîìèöèíà À ñ êàðáîêñèìåòîêñèëàìèíîì [78,79]. Ðåàêöèÿ ïðîòåêàåò ðåãèîñåëåêòèâíî ïî 2¢-êåòîãðóïïå áîêîâîé öåïè, ïðèâîäÿ ê êëþ÷åâîìó ñîåäèíåíèþ -2¢-êàðáîêñèìåòîêñèìîëèâîìèöèíó À. Äðóãîå èññëåäîâàííîå íàïðàâëåíèå ìîäèôèêàöèè (ðèñ.…”

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Оливомицин А — Противоопухолевый Антибиотик Группы Ауреоловой Кислоты (Обзор)

Тевяшова¹

2016

Хим.-фарм. ж.

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Modification of the antibiotic olivomycin I at the 2′-keto group of the side chain. Novel derivatives, antitumor and topoisomerase I-poisoning activity

Cited by 17 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

The next ten stories on antiviral drug discovery (part E): advents, advances, and adventures

Оливомицин А — Противоопухолевый Антибиотик Группы Ауреоловой Кислоты (Обзор)

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