Design, characterization, and evaluation of antibacterial gels, Boc-D-Phe-γ4-L-Phe-PEA/chitosan and Boc-L-Phe-γ4-L-Phe-PEA/chitosan, for biomaterial-related infections

Malhotra, Kamal; Shankar, Sudha; Chauhan, Neelam; Rai, Rajkishor; Singh, Yashveer

doi:10.1016/j.msec.2020.110648

Cited by 19 publications

(11 citation statements)

References 45 publications

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“…All peptides showed bands at ∼230 nm, indicative of π–π stacking of aromatic phenylalanine residues . The intense band around 230 nm in peptides indicates beta-sheet, while the peaks around 210 and 224 nm can be assigned to α-helix or random coil, suggesting features of both α-helix and β-sheet for Fmoc-FF peptide. , The antiparallel β-sheet structure and random coils were also indicated by the FTIR peaks ,, at 1245–1248 and 1649 cm –1 . The average zeta potential of FF, HFF, and RFF peptides in PBS (pH: 7.4) was +5.53, 5.93, and 16.9.…”

Section: Resultsmentioning

confidence: 89%

Self-Assembled Fmoc-Arg-Phe-Phe Peptide Gels with Highly Potent Bactericidal Activities

Chauhan

Singh

2020

ACS Biomater. Sci. Eng.

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The emergence of antibiotic resistance and the increasing rate of bacterial infections have motivated scientists to explore novel antibacterial materials and strategies to circumvent this challenge. Gels fabricated from ultrashort self-assembled peptides have turned out to be the most promising bactericidal materials. Self-assembled Fmoc-Phe-Phe gels have been extensively investigated earlier, and it has been shown that these gels possess potent bactericidal properties but suffer from disadvantages, such as poor proteolytic stabilities. In the present work, we report the highly potent bactericidal activities and proteolytic stability of gels fabricated from Fmoc-l-Arg-d-Phe-d-Phe-CONH2 (RFF) peptide, which are best in class. We fabricated and characterized self-assembled gels (1–2% w/v) from Fmoc-d-Phe-d-Phe-CONH2 (FF), Fmoc-l-His-d-Phe-d-Phe-CONH2 (HFF), and Fmoc-l-Arg-d-Phe-d-Phe-CONH2 (RFF) in aq dimethyl sulfoxide (35% v/v). The gels were characterized for their surface morphology, viscoelastic, self-healing, and stability characteristics. On incubation with proteolytic enzymes, FF gels did not show statistically significant degradation, and HFF and RFF gels showed only 43 and 32% degradation within 72 h at 37 °C, which is much better than gels reported earlier. The RFF gels (2%) exhibited more than 90% inhibition against Escherichia coli (Gram-negative) and Staphylococcus aureus (Gram-positive) within 6 h, and the activities were sustained for up to 72 h. The high-resolution transmission electron microscopy studies indicated electrostatic interactions between the gel and bacterial membrane components, leading to cell lysis and death, which was further confirmed by the bacterial cell Live/Dead assay. MTT assay showed that the gels were not toxic to mammalian cells (L929). The bactericidal characteristics of RFF gels have not been reported so far. The RFF gels show strong potential for treating device-related infections caused by antimicrobial-resistant bacteria.

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Section: Resultsmentioning

confidence: 89%

Self-Assembled Fmoc-Arg-Phe-Phe Peptide Gels with Highly Potent Bactericidal Activities

Chauhan

Singh

2020

ACS Biomater. Sci. Eng.

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“…In addition, low molecular weight gels have been recently discovered for drug delivery [ 10 ]. The use of small peptides containing unnatural amino acids has been proved to be useful in drug delivery, as these chains are hardly recognized by enzymes [ 11 , 12 ]. In addition, a gel of a fluorine derivative of phenylalanine (Fmoc-F 5 -Phe-DAP, where DAP is 1,3-diaminopropane) has been recently tested as a vehicle for diclofenac in vivo [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Designing a Transparent and Fluorine Containing Hydrogel

Ravarino

Giuri

Faccio

et al. 2021

Gels

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Physical hydrogels are supramolecular materials obtained by self-assembly of small molecules called gelators. Aromatic amino acids and small peptides containing aromatic rings are good candidates as gelators due to their ability to form weak bonds as π-π interactions and hydrogen bonds between NH and CO of the peptide chain. In this paper we show our results in the preparation of a transparent hydrogel that was obtained by self-assembly of a fluorine-containing dipeptide that relies on the additional formation of halogen bonds due to the fluorine atoms contained in the dipeptide. We used Boc-D-F2Phe-L-Oxd-OH (F2Phe = 3,4-difluorophenylalainine; Oxd = 4-methyl-5-carboxy-oxazolidin-2-one) that formed a strong and transparent hydrogel in 0.5% w/w concentration at pH = 4.2. The formation of a hydrogel made of unnatural fluorinated amino acids may be of great interest in the evaluation of patients with parkinsonian syndromes and may be used for controlled release.

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“…It could produce the bionic structure, and its composition was close to the natural composition of bone tissue (Skwarczynska et al 2019). The self-assembled peptide/chitosan gels, such as Boc-d-Phe-γ 4 -l-Phe-PEA/chitosan and Boc-l-Phe-γ 4 -l-Phe-PEA/chitosan, showed broad spectrum antibacterial activities against Gram-negative and Gram-positive bacteria, and the antibacterial activities were sustained for up to 48 h (Malhotra et al 2020). And the injectable chitosan/dextran/β-glycerophosphate hydrogel was a promising candidate as a cell delivery carrier for therapy of myocardial infarction (Ke et al 2020).…”

Section: Introductionmentioning

confidence: 99%

Design and evaluation of chitosan-amino acid thermosensitive hydrogel

Tong

Zhou

et al. 2021

Mar Life Sci Technol

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Chitosan/glycerophosphate thermosensitive hydrogel crosslinked physically was a potential drug delivery carrier; however, long gelation time limits its application. Here, chitosan-amino acid (AA) thermosensitive hydrogels were prepared from chitosan (CS), αβ-glycerophosphate (GP), and l-lysine (Lys) or l-glutamic acid (Glu). The prepared CS-Lys/GP and CS-Glu/GP hydrogel showed good thermosensitivity and could form gels in a short time. The optimal parameters of CS-Lys/ GP hydrogel were that the concentration of CS-Lys was 2.5%, the ratio of CS/Lys was 3.5/1.0, the ratio of CS-Lys/GP was 4.5/1.0. The optimal parameters of CS-Glu/GP hydrogel were that the concentration of CS-Glu was 3.0%, the ratio of CS/ Glu was 2.0/1.0, and the ratio of CS-Glu/GP was 4.0/1.5. Chitosan-amino acid (CS-AA) thermosensitive hydrogel had a three-dimensional network structure. The addition of model drug tinidazole (TNZ) had no obvious effect on the structure of hydrogel. The results of infrared spectroscopy showed that there were hydrogen bonds between amino acids and chitosan. In vitro release results showed that CS-Lys/GP and CS-Glu/GP thermosensitive hydrogels had sustained release effects. Thus, the chitosan-amino acid thermosensitive hydrogels hold great potential as a sustained release drug delivery system.

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Design, characterization, and evaluation of antibacterial gels, Boc-D-Phe-γ4-L-Phe-PEA/chitosan and Boc-L-Phe-γ4-L-Phe-PEA/chitosan, for biomaterial-related infections

Cited by 19 publications

References 45 publications

Self-Assembled Fmoc-Arg-Phe-Phe Peptide Gels with Highly Potent Bactericidal Activities

Self-Assembled Fmoc-Arg-Phe-Phe Peptide Gels with Highly Potent Bactericidal Activities

Designing a Transparent and Fluorine Containing Hydrogel

Design and evaluation of chitosan-amino acid thermosensitive hydrogel

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