- Cytotoxic activities and metabolic studies of new combretastatin analogues
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A new series of combretastatin analogues with B-ring modifications were synthesized and evaluated for their cytotoxicity against one endothelial (HUVEC) and three tumor cell lines, e.g., the LoVo colon, the PC-3 prostate, and the U373 glioma cancer models. These new combretastatin analogues showed differential cytotoxic activities, cis derivatives 13 5-(2-Z-trimethoxyphenylethenyl)benzo[1,2-c]1,2,5-oxadiazole N 1-oxide and 14 5-(2-Z-trimethoxyphenylethenyl)benzo[1,2,5]thiadiazole exhibiting interesting cytotoxicity both on endothelial and on tumor cells. Unlike the cis benzofurazan 12 5-(2-Z-trimethoxyphenylethenyl)benzo[1,2-c]1,2,5-oxadiazole, induction of apoptosis by 13 appeared to be through caspase-3 activation. Metabolic investigations showed a positive correlation between highly metabolized compounds and cytotoxic activity, suggesting that highly cytotoxic derivatives may act as pro-drug via a reductive metabolization to more active metabolites.
- Macé, Yohan,Bony, Emilie,Delvaux, David,Pinto, Adan,Mathieu, Véronique,Kiss, Robert,Feron, Olivier,Quetin-Leclercq, Jo?lle,Riant, Olivier
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- Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole -Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
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Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.
- G?bel, Dominik,Rusch, Pascal,Duvinage, Daniel,Stauch, Tim,Bigall, Nadja-C.,Nachtsheim, Boris J.
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p. 14333 - 14355
(2021/10/20)
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