Antibacterial Activity of Cysteine-Derived Cationic Dipeptides

Tsai, Yu Cheng; Tang, Chengzhou; Wu, Hsu Heng; Wang, Yu Shiang; Chen, Yu Fon

doi:10.1007/s10989-019-09913-4

Cited by 9 publications

(16 citation statements)

References 38 publications

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“…The results also indicated a synergistic enhancement in the antimicrobial activity of WO 3 NPs via modi cation with the applied amino acids as WO 3 -Cys revealed higher broad-spectrum antibacterial activity toward Staphylococcus aureus and Pseudomonas aeruginosa compared to MIC values of Cys (85.82 and 112.7 µg/ml), with limited antifungal activity toward Candida albicans (105.9 µg/ml) compared to that of Cys (115 µg/ml). The results are in accordance with other's ndings stated the potency of Cys and Cys-rich peptides as promising antibacterial agents 46,55 . Recently, short peptides and amino acids-rich biomolecules rise as promising bacteriostatic agents that most likely targeting outer bacterial membrane rather than intracellular bacterial structures 46,56 .…”

Section: Separate Cys and Trp Revealed Considerable Antimicrobial Activity Compared To That Of Trp And Wosupporting

confidence: 92%

“…The results are in accordance with other's ndings stated the potency of Cys and Cys-rich peptides as promising antibacterial agents 46,55 . Recently, short peptides and amino acids-rich biomolecules rise as promising bacteriostatic agents that most likely targeting outer bacterial membrane rather than intracellular bacterial structures 46,56 . The thiol side chain in cysteine is highly reactive and hypothetically initiate the rst interaction toward bacterial cell membranes 46,57 .…”

Section: Separate Cys and Trp Revealed Considerable Antimicrobial Activity Compared To That Of Trp And Wosupporting

confidence: 92%

“…Recently, short peptides and amino acids-rich biomolecules rise as promising bacteriostatic agents that most likely targeting outer bacterial membrane rather than intracellular bacterial structures 46,56 . The thiol side chain in cysteine is highly reactive and hypothetically initiate the rst interaction toward bacterial cell membranes 46,57 . On the other hand, WO 3 -Trp also revealed broad-spectrum antibacterial activity toward Staphylococcus aureus (MIC 72.5 µg/ml) and Pseudomonas aeruginosa (MIC 104.7 µg/ml) with strong antifungal activity toward Candida albicans (42.8 µg/ml).…”

Section: Separate Cys and Trp Revealed Considerable Antimicrobial Activity Compared To That Of Trp And Womentioning

confidence: 99%

“…Currently, a wide interest in the individual AAs' interaction with different NPs for better understanding and elucidation of corona-like structure and give a deeper insight for the new resulting biological activity 44,45 . Cysteine and tryptophanrich short peptides revealed potent antimicrobial activity against many human pathogens 46,47 . The current study concerning the preparation and functionalization of WO 3 NPs with tryptophan or cysteine amino acids and evaluating the e cacy of the resulted NPs-AAs in versatile applications including synthetic dye removal, antimicrobial, and antitumor activities.…”

Section: Introductionmentioning

confidence: 99%

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Novel Nanocombinations of L-tryptophan and L-cysteine: Preparation, Characterization and Their Applications for Dye Decolorization, Antimicrobial and Anticancer Activities

Abd-Elhamid

El‐Gendi

Abdallah

et al. 2021

Preprint

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Tungsten oxide WO3 nanoparticles (NPs) were prepared in a form of nanosheets with a homogeneous size and dimensions in one step through acid precipitation using a cation exchange column. The resulting WO3 nanosheets surface was decorated with one of the two amino acids (AAs) L-tryptophan (Trp) or L-cysteine (Cys) for their dye removal, antimicrobial, and antitumor activities. A noticeable improvement in the biological activity of WO3 NPs was detected upon amino acid modification compared to the original WO3. The prepared WO3-Trp and WO3-Cys exhibited strong dye removal activity toward methylene blue and safranin dyes with complete dye removal (100%) after 6 h. WO3-Cys NPs and WO3-Trp NPs revealed higher broad-spectrum antibacterial activity toward both G-ve and G+ve bacteria with strong antifungal activity toward Candida albicans. Anticancer results of the modified WO3-Cys and WO3-Trp NPs against various kinds of cancer cells including MCF-7, caco-2, and HepG-2 cells indicated that they have a potent effect in a dose-dependent manner with high selectivity to cancer cells and safety against normal cells. The expression levels of E2F2, Bcl-2 genes were found to be suppressed after treatment with both WO3-Cys and WO3-Trp NPs more than 5-FU-treated cells. While expression level of the p53 gene in all tested cells was evidently up-regulated after treatment by more than 5-8 folds as compared to untreated cells. The docking results confirmed the ability of both NPs to bind to P53 gene with relevant potency in binding to other tested gens and participation of cysteine SH-functional group in such interaction.

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Section: Separate Cys and Trp Revealed Considerable Antimicrobial Activity Compared To That Of Trp And Wosupporting

confidence: 92%

Section: Separate Cys and Trp Revealed Considerable Antimicrobial Activity Compared To That Of Trp And Wosupporting

confidence: 92%

Section: Separate Cys and Trp Revealed Considerable Antimicrobial Activity Compared To That Of Trp And Womentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Novel Nanocombinations of L-tryptophan and L-cysteine: Preparation, Characterization and Their Applications for Dye Decolorization, Antimicrobial and Anticancer Activities

Abd-Elhamid

El‐Gendi

Abdallah

et al. 2021

Preprint

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“…Similarly, the addition of L-cysteine to AMPs (Andersonin-Y1, HBcARD, buforinII or lysin) enhanced its antimicrobial activity, with higher membrane disruption activity than the original peptide ( Chen et al, 2018 ; Pal et al, 2019 ). The cysteine-derived cationic dipeptides lysine–cysteine, arginine–cysteine and histidine–cysteine presented antimicrobial activity, SEM analysis suggests that these dipeptides interact with cell walls to disrupt membrane integrity ( Tsai et al, 2020 ). Whereas addition of an L-cysteine to the C-terminus of indolicidin, magainine or epinecidin-1 did not change their antimicrobial activity ( Chen et al, 2018 ).…”

Section: Discussionmentioning

confidence: 99%

Addition of L-cysteine to the N- or C-terminus of the all-D-enantiomer [_D(KLAKLAK)₂] increases antimicrobial activities against multidrug-resistant Pseudomonas aeruginosa, Acinetobacter baumannii and Escherichia coli

Ohno

Kirikae

Yoshihara

et al. 2020

PeerJ

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Background Antimicrobial peptides have a broad spectrum of antimicrobial activities and are attracting attention as promising next-generation antibiotics against multidrug-resistant (MDR) bacteria. The all-d-enantiomer [D(KLAKLAK)2] has been reported to have antimicrobial activity against Escherichia coli and Pseudomonas aeruginosa, and to be resistant to protein degradation in bacteria because it is composed of D-enantiomer compounds. In this study, we demonstrated that modification of [D(KLAKLAK)2] by the addition of an L-cysteine residue to its N- or C- terminus markedly enhanced its antimicrobial activities against Gram-negative bacteria such as MDR Acinetobacter baumannii, E. coli, and P. aeruginosa. Methods The peptides [D(KLAKLAK)2] (DP), DP to which L-cysteine was added at the N-terminus C-DP, and DP to which L-cysteine was added at the C-terminus DP-C, were synthesized at >95% purity. The minimum inhibitory concentrations of peptides and antibiotics were determined by the broth microdilution method. The synergistic effects of the peptides and the antibiotics against MDR P. aeruginosa were evaluated using the checkerboard dilution method. In order to assess how these peptides affect the survival of human cells, cell viability was determined using a Cell Counting Kit-8. Results C-DP and DP-C enhanced the antimicrobial activities of the peptide against MDR Gram-negative bacteria, including A. baumannii, E. coli, and P. aeruginosa. The antimicrobial activity of DP-C was greater than that of C-DP, with these peptides also having antimicrobial activity against drug-susceptible P. aeruginosa and drug-resistant P. aeruginosa overexpressing the efflux pump components. C-DP and DP-C also showed antimicrobial activity against colistin-resistant E. coli harboring mcr-1, which encodes a lipid A modifying enzyme. DP-C showed synergistic antimicrobial activity against MDR P. aeruginosa when combined with colistin. The LD50 of DP-C against a human cell line HepG2 was six times higher than the MIC of DP-C against MDR P. aeruginosa. The LD50 of DP-C was not altered by incubation with low-dose colistin. Conclusion Attachment of an L-cysteine residue to the N- or C-terminus of [D(KLAKLAK)2] enhanced its antimicrobial activity against A. baumannii, E. coli, and P. aeruginosa. The combination of C-DP or DP-C and colistin had synergistic effects against MDR P. aeruginosa. In addition, DP-C and C-DP showed much stronger antimicrobial activity against MDR A. baumannii and E. coli than against P. aeruginosa.

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Green synthesis of novel antifungal 1,2,4‐triazoles effective against γ‐irradiated Candida parapsilosis

El‐Hazek

Elkenawy

Zaher

et al. 2021

Archiv der Pharmazie

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This study reports the green synthesis of 11 novel 3-substituted-4-amino-5mercapto-1,2,4-triazole derivatives using water as a readily available nontoxic solvent. Evaluation of their antimicrobial potential against several clinical pathogenic microorganisms was carried out. The newly synthesized cysteine derivative 6 showed promising antifungal activity against both γ-irradiated and nonirradiated Candida parapsilosis 216, with the lowest MIC (minimum inhibitory concentration) value of 3.125 µg/ml, probably through inhibition of 14α-demethylase. In addition, compound 6 showed complete inhibition of gelatinase, a virulence enzyme of C. parapsilosis. Also, scanning electron microscopy was carried out. Interestingly, compound 6 acted as a dual agent as it also showed good antibacterial activity against strains of Gram-positive bacteria used in the study. The synthesized compounds showed no cytotoxicity.

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Antibacterial Activity of Cysteine-Derived Cationic Dipeptides

Cited by 9 publications

References 38 publications

Novel Nanocombinations of L-tryptophan and L-cysteine: Preparation, Characterization and Their Applications for Dye Decolorization, Antimicrobial and Anticancer Activities

Novel Nanocombinations of L-tryptophan and L-cysteine: Preparation, Characterization and Their Applications for Dye Decolorization, Antimicrobial and Anticancer Activities

Addition of L-cysteine to the N- or C-terminus of the all-D-enantiomer [_D(KLAKLAK)₂] increases antimicrobial activities against multidrug-resistant Pseudomonas aeruginosa, Acinetobacter baumannii and Escherichia coli

Green synthesis of novel antifungal 1,2,4‐triazoles effective against γ‐irradiated Candida parapsilosis

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Antibacterial Activity of Cysteine-Derived Cationic Dipeptides

Cited by 9 publications

References 38 publications

Novel Nanocombinations of L-tryptophan and L-cysteine: Preparation, Characterization and Their Applications for Dye Decolorization, Antimicrobial and Anticancer Activities

Novel Nanocombinations of L-tryptophan and L-cysteine: Preparation, Characterization and Their Applications for Dye Decolorization, Antimicrobial and Anticancer Activities

Addition of L-cysteine to the N- or C-terminus of the all-D-enantiomer [D(KLAKLAK)2] increases antimicrobial activities against multidrug-resistant Pseudomonas aeruginosa, Acinetobacter baumannii and Escherichia coli

Green synthesis of novel antifungal 1,2,4‐triazoles effective against γ‐irradiated Candida parapsilosis

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Resources

About

Addition of L-cysteine to the N- or C-terminus of the all-D-enantiomer [_D(KLAKLAK)₂] increases antimicrobial activities against multidrug-resistant Pseudomonas aeruginosa, Acinetobacter baumannii and Escherichia coli