Cinnamic Derivatives in Tuberculosis

De, Prithwiraj; Veau, Damien; Bedos‐Belval, Florence; Chassaing, Stefan; Baltas, Michel

doi:10.5772/31382

Cited by 11 publications

(11 citation statements)

References 86 publications

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“…These molecules had broad spectrum activity causing significant changes in cell surface hydrophobicity, charge and induced K + leakage, an effect more significant for S. aureus. Moreover, as some cinnamic derivatives, have demonstrated good efficacy in the treatment of patients with tuberculosis 65 , the CAF alkyl esters are of potential interest to be used against Mycobacterium tuberculosis. Indeed, cinnamic derivatives already revelead high potency and selectivity against this bacterium, with MIC only at micromolars.…”

Section: Discussionmentioning

confidence: 99%

“…13 C NMR (CDCl 3 ): 14.1 (C(10')), 22.7 (C(9')), 26.0 (C(8')), 28.7 (C(7')), 29.3 (C(6'), C(5')), 29.6 (C(4'), C(3')), 31.9 (C(2')), 65.0 (C(1')), 114.5 (C (2) . Stock solutions of all tested compounds were prepared in dimethyl sulfoxide (DMSO, Fisher), under sterile conditions, and kept in the dark, at room temperature, for a maximum of two weeks.…”

Section: Trans-hexylmentioning

confidence: 99%

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Fine-tuning of the hydrophobicity of caffeic acid: studies on the antimicrobial activity against Staphylococcus aureus and Escherichia coli

et al. 2015

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The increased bacterial multidrug resistance caused by inappropriate use and overuse of antimicrobials is a global concern. To circumvent this issue, a quest for the development of new active agents has been widely recognized. Some phytochemical products, produced by plants as part of their chemical defense strategies, are regarded as new stimulus to develop novel antimicrobials that are not as vulnerable as current drugs to bacterial resistance mechanisms. In this study, the antimicrobial activity and mode of action of caffeic acid (CAF) and a series of CAF alkyl esters was assessed against Escherichia coli and Staphylococcus aureus, with the aim of analyzing the influence of the alkyl ester side chain length on the activity. Minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), changes in physicochemical surface properties and intracellular potassium leakage were used as physiological indices for the antimicrobial mode of action. CAF alkyl esters were found to be effective antimicrobial agents against both bacteria. Their activity was directly dependent on their lipophilicity, which affected bacterial susceptibility, the physicochemical properties of the bacteria and the integrity of the membranes. E. coli was less susceptible than S. aureus to the action of the compounds. Longer alkyl side chains were more effective against the Gram-positive bacterium, while medium length alkyl side chain compounds were more effective against the Gram-negative bacterium. Caffeic acid derivatives are proposed to act as cell permeabilizers, inducing membrane alterations, causing rupture with potassium leakage, particularly on the Gram positive bacterium, and consequent cell death.

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Section: Discussionmentioning

confidence: 99%

Section: Trans-hexylmentioning

confidence: 99%

Fine-tuning of the hydrophobicity of caffeic acid: studies on the antimicrobial activity against Staphylococcus aureus and Escherichia coli

et al. 2015

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“…Our group is involved both in synthesizing new antitubercular compounds, including cinnamic acid derivatives [ 26 , 27 , 28 , 29 ], triazoles [ 30 , 31 , 32 , 33 ], pyrrolidines [ 34 , 35 , 36 ], semicarbazones and hydrazine/hydrazones [ 37 ], and in searching for new and innovative synthetic reactions. We have recently reported the solvent-free mechanosynthesis of a series of hydrazones [ 38 , 39 ].…”

Section: Introductionmentioning

confidence: 99%

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

et al. 2017

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A series of isoniazid derivatives bearing a phenolic or heteroaromatic coupled frame were obtained by mechanochemical means. Their pH stability and their structural (conformer/isomer) analysis were checked. The activity of prepared derivatives against Mycobacterium tuberculosis cell growth was evaluated. Some compounds such as phenolic hydrazine 1a and almost all heteroaromatic ones, especially 2, 5 and 7, are more active than isoniazid, and their activity against some M. tuberculosis MDR clinical isolates was determined. Compounds 1a and 7 present a selectivity index >1400 evaluated on MRC5 human fibroblast cells. The mechanism of action of selected hydrazones was demonstrated to block mycolic acid synthesis due to InhA inhibition inside the mycobacterial cell.

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“…In addition, caffeic acid has low cytotoxic potential in vitro against leukemia myeloid cells (HL-60) and also has potential as a chemopreventive agent against skin cancer [11]. Combinations of cinnamic acid and guanylhydrazone compounds that have also been synthesized have high activity against Mycobacterium active tuberculosis H37Rv which is the causative agent of tuberculosis (TB) [7]. Bairwa et al [6] reported that the synthesis of cinnamic acid with thionyl chloride to produce halides acid.…”

Section: Introductionmentioning

confidence: 99%

“…Cinnamic acid, originally isolated from plant [1], has been widely reported to have a wide range of bioactivity such as anticancer [2], antitumor [3], anti-inflammatory [4], antioxidant [5], antimalarial, antituberculosis [6][7], antimicrobial [8], tyrosinase inhibitor [9], and antidiabetic [10]. For example, trans-cinnamic acid induces cytostasis and reversal of malignant properties of human tumor cells in vitro.…”

Section: Introductionmentioning

confidence: 99%