Studies on the mode of interaction of 4'-epi-adriamycin and 4-demethoxy-daunomycin with DNA

Plumbridge, Terence W.; Brown, Jeffrey R.

doi:10.1016/0006-2952(78)90037-0

Cited by 45 publications

(6 citation statements)

References 4 publications

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“…Since the molecular inhibition mechanism of idarubicin is not different from that of the other anthracyclines tested in this study (Plumbridge & Brown 1978), why is idarubicin the only compound displaying trypanocidal activity against T. rangeli? The answer to this question may lie in the structure of the molecules.…”

mentioning

confidence: 88%

Differential in vitro activity of the DNA topoisomerase inhibitor idarubicin against Trypanosoma rangeli and Trypanosoma cruzi

Jobe

Anwuzia-Iwegbu

Banful

et al. 2012

Mem. Inst. Oswaldo Cruz

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mentioning

confidence: 88%

Differential in vitro activity of the DNA topoisomerase inhibitor idarubicin against Trypanosoma rangeli and Trypanosoma cruzi

Jobe

Anwuzia-Iwegbu

Banful

et al. 2012

Mem. Inst. Oswaldo Cruz

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“…The fluorescence emission of drugs bound to DNA can be either enhanced, as observed for ethidium bromide, 24 or efficiently quenched, as found for certain aminoacridines and anthracyclines, including daunomycin 25 and adriamycin. 26 Triazolopyridopyrimidines 1a-1c are fluorescent compounds, so their DNA interaction was also studied by measuring the changes in their fluorescence emission in the presence of DNA.…”

Section: Luminescence Titrationsmentioning

confidence: 99%

Triazolopyridopyrimidines: an emerging family of effective DNA photocleavers. DNA binding. Antileishmanial activity

et al. 2015

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Triazolopyridopyrimidines 3-phenyl-6,8-di(2-pyridyl)-[1,2,3]triazolo[5',1':6,1]pyrido[2,3-d]pyrimidine (1a), 6,8-di(pyridin-2-yl)-[1,2,3]triazolo[1',5':1,6]pyrido[2,3-d]pyrimidine (1b) and 3-methyl-6,8-di(2-pyridyl)-[1,2,3]triazolo[5',1':6,1]pyrido[2,3-d]pyrimidine (1c) were prepared and their electrochemical and luminescence properties were studied in depth. The DNA binding ability of this series of compounds has been investigated by means of UV-vis absorption and fluorescence titrations, steady-state emission quenching with ferrocyanide as well as viscosity measurements. Results have shown that triazolopyridopyrimidine 1a interacts strongly at DNA grooves. This compound also displays preferential binding to GC-rich sequences and the ability to photooxidize guanine. Moreover, these studies have revealed the key role of the phenyl substituent at the triazole ring in the binding affinity of 1a-c. Compounds 1b and 1c did not show appreciable propensity for DNA binding, however these triazolopyridopyrimidines demonstrated to present photoinduced DNA cleavage activity, 1b being more active than 1c. DNA photocleavage mediated by these compounds takes place mainly through single strand scission events and, in a minor extent, through double strand cuts. Mechanistic investigations using radical scavengers showed that both 1b and 1c generate reactive oxygen species (singlet oxygen, superoxide and hydroxyl radicals) upon irradiation. Both type I and type II mechanisms are involved in the photocleavage process. Furthermore, compounds 1a-c were tested for their antiprotozoal activity against four different Leishmania spp. (L. infantum, L. braziliensis, L. guyanensis and L. amazonensis). Triazolopyridopyrimidines 1a and 1c resulted to be more active and selective than the reference drug (miltefosine) in vitro against L. infantum amastigotes. Compound 1a exhibited high leishmanicidal activity against L. infantum spleen forms in the in vivo test.

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“…Idarubicin in induction therapy IDR, a lipophilic analogue of DNR, has been extensively tested as part of the 7 + 3 backbone in AML. It is structurally identical to DNR except for a change at position 4 of its chromophore ring conferring a higher lipophilic coefficient, induction of more DNA single-strand breaks in tumor cells, and an active metabolite with a longer halflife as compared with DNR in vitro [Zunino et al 1976;Supino et al 1977;Plumbridge et al 1978;Speth et al 1986]. After phase I testing revealed a myelosuppressive dose-limiting toxicity of 12 mg/ m 2 , phase II studies were performed in Italy, France, and the United States demonstrating that IDR as a single agent induced CR in 13-22% of adult patients with relapsed or refractory AML [Hayat et al 1984;Daghestani et al 1985;Gillies et al 1987].…”

Section: Other Anthracyclinesmentioning

confidence: 99%

Anthracycline dose intensification in young adults with acute myeloid leukemia

Padron¹,

Fernandez²

2011

Therapeutic Advances in Hematology

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Studies on the mode of interaction of 4'-epi-adriamycin and 4-demethoxy-daunomycin with DNA

Cited by 45 publications

References 4 publications

Differential in vitro activity of the DNA topoisomerase inhibitor idarubicin against Trypanosoma rangeli and Trypanosoma cruzi

Differential in vitro activity of the DNA topoisomerase inhibitor idarubicin against Trypanosoma rangeli and Trypanosoma cruzi

Triazolopyridopyrimidines: an emerging family of effective DNA photocleavers. DNA binding. Antileishmanial activity

Anthracycline dose intensification in young adults with acute myeloid leukemia

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