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  • Novel capsaicin analogues as potential anticancer agents: synthesis, biological evaluation, and in silico approach.

Novel capsaicin analogues as potential anticancer agents: synthesis, biological evaluation, and in silico approach.

Archiv der Pharmazie (2014-10-07)
Mariana C F C B Damião, Kerly F M Pasqualoto, Adilson K Ferreira, Sarah F Teixeira, Ricardo A Azevedo, José A M Barbuto, Fanny Palace-Berl, Gilberto C Franchi-Junior, Alexandre E Nowill, Maurício T Tavares, Roberto Parise-Filho
ABSTRACT

A novel class of benzo[d][1,3]dioxol-5-ylmethyl alkyl/aryl amide and ester analogues of capsaicin were designed, synthesized, and evaluated for their cytotoxic activity against human and murine cancer cell lines (B16F10, SK-MEL-28, NCI-H1299, NCI-H460, SK-BR-3, and MDA-MB-231) and human lung fibroblasts (MRC-5). Three compounds (5f, 6c, and 6e) selectively inhibited the growth of aggressive cancer cells in the micromolar (µM) range. Furthermore, an exploratory data analysis pointed at the topological and electronic molecular properties as responsible for the discrimination process regarding the set of investigated compounds. The findings suggest that the applied designing strategy, besides providing more potent analogues, indicates the aryl amides and esters as well as the alkyl esters as interesting scaffolds to design and develop novel anticancer agents.

MATERIALS
Product Number
Brand
Product Description

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Benzoic acid, Pharmaceutical Secondary Standard; Certified Reference Material
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Melting point standard 121-123°C, analytical standard
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Propionic acid, puriss. p.a., ≥99.5% (GC)
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Benzoic acid, meets analytical specification of Ph. Eur., BP, USP, FCC, E210, 99.5-100.5% (alkalimetric)
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Butyric acid, natural, ≥99%, FCC, FG
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Benzoic acid, ReagentPlus®, 99%
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Benzoic acid, purified by sublimation, ≥99%
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Benzoic acid, ACS reagent, ≥99.5%
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Isovaleric acid, natural, ≥98%, FG
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Propionic acid, ACS reagent, ≥99.5%
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Propionic acid, BioReagent, suitable for insect cell culture, ~99%
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Benzoic acid, United States Pharmacopeia (USP) Reference Standard
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Benzoic acid, Standard for quantitative NMR, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Benzoic acid, European Pharmacopoeia (EP) Reference Standard
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Isovaleric acid, analytical standard
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Melting point standard 182-184°C, analytical standard