Biologically active l-cysteine as a reducing/capping agent for controlled tuning of gold nanoparticles

Sharma, Bindu; Rabinal, M. K.

doi:10.1016/j.jallcom.2015.06.160

Cited by 20 publications

(21 citation statements)

References 53 publications

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“…ʟ‐cysteine, a part of some polypeptide proteins, is environmentally friendly and is important in the manufacture of various pharmaceutical products. ʟ‐cysteine ethyl ester with a chiral carbon contains thiol, amine, and ester groups . Chirality is an important subject in pharmaceutical drug development.…”

Section: Introductionmentioning

confidence: 99%

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Novel fluorine‐containing chiral hydrazide‐hydrazones: Design, synthesis, structural elucidation, antioxidant and anticholinesterase activity, andin silicostudies

et al. 2019

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In this study, a series of fluorine‐containing chiral hydrazide‐hydrazone derivatives [III‐XII] from ʟ‐cysteine ethyl ester hydrochloride was synthesized as new antioxidant and anticholinesterase agents. The antioxidant activity of these derivatives was evaluated by ABTS+· and DPPH· scavenging and CUPRAC assays and the anticholinesterase activity by the Ellman method spectrophotometrically. The results of the antioxidant assay showed that compounds V, IX, and X exhibited higher activity than BHT and α‐tocopherol used as positive standards. Among the synthesized derivatives, compound IX (IC50: 2.3 ± 1.6 μM) exhibited higher acetylcholinesterase inhibitory activity than galantamine (IC50: 4.5 ± 0.8 μM). Compounds XI (IC50: 9.6 ± 1.0 μM), IX (IC50: 12.5 ± 1.6 μM), III (IC50: 16.0 ± 1.6 μM), X (IC50: 17.2 ± 1.8 μM), VI (IC50: 20.2 ± 0.8 μM), XII (IC50: 21.5 ± 1.0 μM), and VII (IC50: 24.6 ± 0.6 μM) displayed better butyrylcholinesterase inhibitory activity than galantamine (IC50: 46.03 ± 0.14 μM). ADME‐Tox analysis was used to probe the drug‐like properties of the compounds. Molecular docking studies were also applied to understand the interactions between compounds and targets. The docking calculations were supported by the experimental data. In particular, compound IX, having better activity than galantamine against acetylcholinesterase and butyrylcholinesterase enzymes, was visualized using molecular docking.

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Section: Introductionmentioning

confidence: 99%

“…ʟ-cysteine ethyl ester with a chiral carbon contains thiol, amine, and ester groups. 8 Chirality is an important subject in pharmaceutical drug development. More than half of existing drugs used in medical treatments are chiral molecules.…”

Section: Introductionmentioning

confidence: 99%

Novel fluorine‐containing chiral hydrazide‐hydrazones: Design, synthesis, structural elucidation, antioxidant and anticholinesterase activity, andin silicostudies

et al. 2019

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“…Reagents and stock solutions L-Cysteine, FAD, nitrate reductase (NR) and laccase (LAC) were purchased from Sigma Aldrich, St Louis, MO, USA; ⊎-nicotinamide adenine dinucleotide 2-phosphate (⊎-NADPH) and hydroquinone (HQ) were purchased from Winkler (Santiago, Chile) and all reagents were used as fungal metabolites according to the reported literature. 12,[21][22][23] NaOH and AgNO 3 were purchased from Merck, Darmstadt, Germany. For the antimicrobial activity assay, Mueller Hinton media (broth and agar) were purchased from Merck (Santiago, Chile).…”

Section: Methodsmentioning

confidence: 99%

“…Lately, one of the most accepted mechanisms for the fungal synthesis of AgNPs is that the thiol groups from proteins containing L-cysteine (L-cys) in the mycelium-free fungal extract are responsible for the reduction of silver. [20][21][22] L-Cysteine is a polar amino acid with a nucleophilic thiol and has been described as covalently bonded with Ag + forming Ag S, acting as a reductant and stabilizer of Ag + to Ag 0 . The use of L-cys alone does not produce nanostructures; however, combined with other reductant biomolecules found in the free-mycelium fungal extract, we found that it can confer interesting properties such as the formation of stable AgNPs with thiol groups that can act as a bond with other compounds.…”

Section: Introductionmentioning

confidence: 99%

Development of a new biomimetic method for the synthesis of silver nanoparticles based on fungal metabolites: optimization and antibacterial activity

Cisternas

Seabra

Pieretti

et al. 2021

J of Chemical Tech & Biotech

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BACKGROUND: A biomimetic method was developed for the synthesis of silver nanoparticles (AgNPs). Synthetic chemical compounds were used according to the metabolites present in the fungal extracts for the synthesis of AgNPs. The main objective of this study was to find a simple and effective synthesis method without the presence of a living organism. METHODOLOGY: A central composite design combined with response surface methodology was used to optimize the necessary metabolite concentrations (flavin adenine dinucleotide (FAD), hydroquinone (HQ), and L-cysteine (L-cys)) for the synthesis of AgNPs. The design was assessed based on the size distribution and zeta potential of the nanoparticles. In addition, the antibacterial activity of the AgNPs against Escherichia coli, Staphylococcus aureus, Serratia marcescens and Salmonella enterica was tested. RESULTS:The results demonstrated that AgNO 3 (2 mmol L −1 ), HQ (20 mmol L −1 ), L-cys (20 mmol L −1 ) and FAD (50.5 nmol L −1 ) at pH 8.4 were the optimal reaction parameters. The characterization allowed the determination of quasi-spherical AgNPs with an average hydrodynamic size of 101 nm, a zeta potential of −24 mV and the presence of elemental silver (Ag 0 ) in their composition. Fourier transform infrared spectroscopy showed silver and L-cys interactions, supporting the role of L-cys as a coating agent. The antibacterial activity showed that AgNPs displayed a minimum inhibitory concentration of 20-30 ∼g mL −1 and a minimum bactericidal concentration of 30-40 ∼g mL −1 .CONCLUSIONS: This study demonstrates the feasibility of the reduction of Ag + to Ag 0 using synthetic metabolites, which mimic the reduction and synthesis of fungal biomass. Therefore, it represents a new biocompatible, eco-friendly and fast method to produce AgNPs.

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“…Over the past several years, driven by the need to develop functional smart materials, a variety of metal nanocomposites have been prepared and extensively used in applications such as catalysis, separations, optical, electronics, sensing, energy devices, and drug delivery . As one of the most investigated materials, gold nanocomposites have received great interest due to superior optical, chemical, electrical, and biological properties.…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of Au@PNIPAM‐b‐PPy nanocomposites with thermosensitive and photothermal effects

Zhong

Zhang

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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In this article, we reported a facile method to in-situ synthesize Au@PNIPAM-b-PPy nanocomposites with thermosensitive and photothermal effects using amphiphilic poly(Nisopropylacrylamide)-block-poly(pyrrolylmethylstyrene) (PNI-PAM-b-PPMS) diblock copolymers as ligands. The hydrophobic PPMS block can in-situ reduce AuCl 2 4 to zero-valent gold and simultaneously be oxidatively copolymerized with the free pyrrole monomers to form a crosslinked and conjugated polypyrrole (PPy) layer. The hydrophilic PNIPAM block as a stabilizer can produce highly thermosensitive effect. Moreover, the resultant Au@PNIPAM-b-PPy nanomaterials show a strong absorption in the near infrared (NIR) region, which endowed the system excellent photothermal effect. On the basis of the PPy photothermal and PNIPAM thermosensitive effects, the above Au@PNIPAM-b-PPy nanomaterials show a reversible, soluble-precipitate transition upon the NIR irradiation off-on.

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Biologically active l-cysteine as a reducing/capping agent for controlled tuning of gold nanoparticles

Cited by 20 publications

References 53 publications

Novel fluorine‐containing chiral hydrazide‐hydrazones: Design, synthesis, structural elucidation, antioxidant and anticholinesterase activity, andin silicostudies

Novel fluorine‐containing chiral hydrazide‐hydrazones: Design, synthesis, structural elucidation, antioxidant and anticholinesterase activity, andin silicostudies

Development of a new biomimetic method for the synthesis of silver nanoparticles based on fungal metabolites: optimization and antibacterial activity

Facile synthesis of Au@PNIPAM‐b‐PPy nanocomposites with thermosensitive and photothermal effects

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