Photo-inducible cytotoxic and clastogenic activities of 3,6-di-substituted acridines obtained by acylation of proflavine

Benchabane, Yohann; Giorgio, Carole Di; Boyer, G.; Sabatier, Anne-Sophie; Allegro, Diane; Peyrot, Vincent; Méo, Michel De

doi:10.1016/j.ejmech.2009.01.010

Cited by 24 publications

(11 citation statements)

References 13 publications

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“…In some previous studies, symmetric and non‐symmetric mono/diamidoacridines were developed by mono‐ or di‐acylation of PF to yield the corresponding amides. In our study, we prepared the two symmetric 3‐ and 6‐diphenoxy/ethoxycarbonyl aminoacridine derivatives from PF according to literature reports . We have obtained 3,6‐disubstituted symmetrical analogues of PF using aryl/alkyl chloroformate (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Studies on the interactions of 3,6‐diaminoacridine derivatives with human serum albumin by fluorescence spectroscopy

2014

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This study reports the preparation and investigation of the modes of binding of the two symmetric 3,6-diaminoacridine derivatives obtained from proflavine, which are 3,6-diphenoxycarbonyl aminoacridine and 3,6-diethoxycarbonyl aminoacridine to human serum albumin (HSA). The interaction of HSA with the derivatives was investigated using fluorescence quenching and ultraviolet-visible absorption spectra at pH 7.2 and different temperatures. The results suggest that the derivatives used can interact strongly with HSA and are the formation of HSA-derivative complexes and hydrophobic interactions as the predominant intermolecular forces in stabilizing for each complex. The Stern-Volmer quenching constants, binding constants, binding sites and corresponding thermodynamic parameters ΔH, ΔS and ΔG were calculated at different temperatures. The binding distance (r) ~ 3 nm between the donor (HSA) and acceptors (3,6-diethoxycarbonyl aminoacridine, 3,6-diphenoxycarbonyl aminoacridine and proflavine) was obtained according to Förster's non-radiative energy transfer theory. Moreover, the limit of detection and limit of quantification of derivatives were calculated in the presence of albumin.

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Section: Introductionmentioning

confidence: 99%

Studies on the interactions of 3,6‐diaminoacridine derivatives with human serum albumin by fluorescence spectroscopy

2014

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“…These results are all consistent with our results related to compounds (7) and (9). Also Benchabane et al (2009) determined that carbamate derivatives are more effective than acetamide derivatives against tumour CHO cells. In this study we found the carbamate derivative (9) has more antiproliferative activity than acetamide derivative (8) (Table 2).…”

Section: Antiproliferative Activity Of Compound (3) Against Hela and mentioning

confidence: 99%

Synthesis and antiproliferative activities of some pyrazole-sulfonamide derivatives

et al. 2013

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In this study, a series of pyrazole-sulfonamide derivatives were designed and synthesized from 1-(4-aminophenyl)-4-benzoyl-5-phenyl-N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-3-carboxamide (1). The newly synthesized sulfonamides were characterized by FT-IR, 1 H NMR, 13 C NMR, and elemental analyses. The compounds were tested for their in vitro antiproliferative activities against HeLa and C6 cell lines. The tests were carried out as dose-dependent assay starting from 5 to 100 lg/mL. All compounds showed especially cell selective effect against rat brain tumor cells (C6). Some of the tested compounds (3) and (7) showed promising broad spectrum antitumor activity comparable to the activities of the commonly used anticancer drugs, 5-fluorouracil and cisplatin.

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“…One of possible inhibition mechanisms here may be a dysfunction of lysosomal enzymes (Satonaka et al, 2011). Photo-inducible effects of AO noted above stimulated also screening of potential photosensitizing properties of some new acridine derivatives (Yang et al, 2006;Benchabane et al, 2009). In 2008, Di Giorgio's research team synthesized and studied PDT effects of new thiazolo[5,4-a]acridine derivatives, some of which intercalated into DNA after irradiation.…”

Section: Introductionmentioning

confidence: 99%

Photocleavage of pDNA by bis-imidazolidino and bis-thioureido proflavines

Cisárikováa

Abaffy

Imrich

et al. 2015

Acta Chimica Slovaca

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New photosensitizers are needed for photodynamic antimicrobial and anticancer chemotherapy. Two new groups of proflavine derivatives have been recently prepared and their action on the cancer cells has been investigated by our research team. In this paper, we studied an effect of UV-A irradiation of two groups of proflavines: 3,6-bis((1-alkyl-5-oxo-imidazolidin-2-yliden)imino)acridine hydrochlorides (AcrDIMs) and 1’,1”-(acridin-3,6-diyl)-3’,3”-dialkyldithiourea hydrochlorides (AcrDTUs) on a plasmid DNA (pDNA). These compounds induced a photocleavage of pDNA characteristic by generation of free radicals, single strand DNA breaks and formation of an open circular form of pDNA.

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Photo-inducible cytotoxic and clastogenic activities of 3,6-di-substituted acridines obtained by acylation of proflavine

Cited by 24 publications

References 13 publications

Studies on the interactions of 3,6‐diaminoacridine derivatives with human serum albumin by fluorescence spectroscopy

Studies on the interactions of 3,6‐diaminoacridine derivatives with human serum albumin by fluorescence spectroscopy

Synthesis and antiproliferative activities of some pyrazole-sulfonamide derivatives

Photocleavage of pDNA by bis-imidazolidino and bis-thioureido proflavines

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