Phytotoxicity Study of Ortho-Disubstituted Disulfides and Their Acyl Derivatives

Oliveira, Sarah Christina Caldas; Andrade, Carlos Kleber Z.; Varela, Rosa M.; Molinillo, José M. G.; Macías, Francisco A.

doi:10.1021/acsomega.8b03219

Cited by 13 publications

(15 citation statements)

References 33 publications

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“…Phosphate buffer (2.0 mL, pH 7.4) and BSA solution (1.0 mL, 10 μM) were added to a 1.0 cm quartz cuvette. The solution was excited at 295 nm and scanned in the range of 300-400 nm at 3 different temperatures namely: 298, 308 and 313 K. The BSA solution was then titrated against 15 μL of the disulfide.…”

Section: Thermodynamic Bsa Studiesmentioning

confidence: 99%

“…A number of diaryl disulfide Schiff bases has been demonstrated to act as antibacterial and herbicidal agents [14,15]. Another disulfide analogue, the bis-chloro-phenyl disulfide has been reported for its effectiveness as potent anticancer agent with specific target the stabilization of the tumor suppressor, programmed cell death 4 (Pdcd4) [16].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and biological properties of a series of aryl alkyl disulfide derivatives

Joondan

Inassee

Bhowon

et al. 2020

Heliyon

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Disulfide containing compounds are recognized for their wide range of biological properties and are known for their important applications in the pharmaceutical field. In this study, a series of diaryl disulfides with varying alkyl chain length (C 8 -C 16 ) was synthesized and assessed for their physicochemical and biological properties. The interactions of compounds with bovine serum albumin (BSA) was investigated in order to study their ability to bind with blood serum protein. An increase in the binding constants (K a ) was observed with increasing chain length C 8 -C 12 , while a decrease in value was obtained with compounds of chain length C 14 and C 16 showing a cut off effect at C 12 . The thermodynamic parameters of binding indicated that the compounds bound to BSA mostly by van der Waals forces and hydrogen bonding. Molecular docking studies showed that the diaryl disulfides displayed greater binding affinity to Trp 213 rather than the Trp 134 residue on the BSA molecule. The trend observed in molecular docking is in line with the fluorescence binding studies whereby the C 12 derivative was found to show optimum affinity with BSA. The disulfide with chain length C 10 showed moderate antibacterial activity the highest inhibitory activity against Bacillus cereus. The cytotoxicity of the disulfides towards HaCaT cells decreased from C 8 to C 14 . The overall results obtained show that these disulfides have potent antibacterial properties against Gram-positive bacteria Bacillus cereus at concentrations which are relatively non-toxic to normal cells.

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Section: Thermodynamic Bsa Studiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and biological properties of a series of aryl alkyl disulfide derivatives

Joondan

Inassee

Bhowon

et al. 2020

Heliyon

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“…The reactions of activity as well as their photochromic properties. [8][9][10][11]. In recent years, antibiotic resistance has become a major problem.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Dimeric Thio-Schiff Bases by Nano Cerium Oxide and Examination of Their Antimicrobial Activities

Dalmaz

Durmuş

Dulger

et al. 2021

Sakarya University Journal of Science

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In this work, firstly, CeO2 nanoparticles, which can be used as catalysts in many reactions, were synthesized by preparing aqueous solution of cerium(III) nitrate hexahydrate in basic medium. In the second step, the synthesis of dimeric thio Schiff bases was carried out using two different methods. Effect of catalyst on some parameters such as reaction time and yield of product were investigated. The antimicrobial activities of the ligands have been screened in vitro against the organisms Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae (Gram negative bacteria), Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Bacillus cereus (Gram positive bacteria) and Candida albicans, C. tropicalis, C. guilliermondii, C. glabrata by Disc Diffusion and Microdilution methods. At the same time, antimicrobial activities of ligands were compared to standard antibiotics (Cefotaxime, Amoxicillin/clavulanic acid, Posacanazole, Nystatin and Gentamicin). Generally, the results obtained in this research showed that all tested ligands exhibited more effect towards Gram positive bacteria and Candida species as compared to standard antibiotics.

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“…This compound was synthesized by the method of Oliveira et al with modifications. [32] 2-Hydroxythiophenol (100 mg, 0.82 μL, 7.93 • 10 À 4 mol) was dissolved in acetone (35 mL). A solution of KIO 3 (1.36 g, 8 equiv.…”

mentioning

confidence: 99%

“…This compound was synthesized by the method of Oliveira et al with modifications. [32] 2-Aminothiophenol (1 g, 0.83 mL, 7.99 • 10 À 3 mol) was dissolved in a 1 : 1 mixture of H 2 O/ethanol (100 mL). The solution was stirred for 18 h with airflow until a solid precipitated.…”

mentioning

confidence: 99%

Acyl Derivatives of Eudesmanolides To Boost their Bioactivity: An Explanation of Behavior in the Cell Membrane Using a Molecular Dynamics Approach

et al. 2021

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Semisynthetic analogs of natural products provide an important approach to obtain safer and more active drugs and they can also have enhanced physicochemical properties such as persistence, cross-membrane processes and bioactivity. Acyl derivatives of different natural product families, from sesquiterpene lactones to benzoxazinoids, have been synthesized and tested in our laboratories. These compounds were evaluated against tumoral and nontumoral cell lines to identify selective derivatives with a reduced negative impact upon application.The mode of action of these compounds was analyzed by anticaspase-3 assays and molecular dynamics simulations with cell membrane re-creation were also carried out. Aryl derivatives of eudesmanolide stand out from the other compounds and are better than current anticancer drugs such as etoposide in terms of selectivity and activity. Computational studies provide evidence that lipophilicity plays a key role and the 4fluorobenzoyl derivative can pass easily through the cell membrane.

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Phytotoxicity Study of Ortho-Disubstituted Disulfides and Their Acyl Derivatives

Cited by 13 publications

References 33 publications

Synthesis and biological properties of a series of aryl alkyl disulfide derivatives

Synthesis and biological properties of a series of aryl alkyl disulfide derivatives

Synthesis and Characterization of Dimeric Thio-Schiff Bases by Nano Cerium Oxide and Examination of Their Antimicrobial Activities

Acyl Derivatives of Eudesmanolides To Boost their Bioactivity: An Explanation of Behavior in the Cell Membrane Using a Molecular Dynamics Approach

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