A new synthesis of the tripeptide Gly-His-Lys with antimicrobial activity

Liakopoulou-Kyriakides, M.; Pachatouridis, Chrysostomos; Ekateriuiadou, L.; Papageorgiou, Vassilios P.

doi:10.1007/bf01373213

Cited by 9 publications

(3 citation statements)

References 14 publications

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“… MRI and specific tumor-targeting properties were conferred by the addition of tripeptide glycine-histidine-lysine (GHK) for Gd 3+ decoration of the shells of aggregates upon self-assembly and the addition of cyclic arginine-glycine-aspartic acid (cRGD) for the recognition of α v β 3 and α v β 5 integrin receptors expressed on tumor cells . GHK peptide is also known to show antimicrobial activity . Herein, we report on short peptide-based cancer-targeting, theranostic nanoagents with antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

“…28 GHK peptide is also known to show antimicrobial activity. 29 Herein, we report on short peptidebased cancer-targeting, theranostic nanoagents with antimicrobial activity. Their MRI contrast characteristics were investigated as a function of nanoagent morphology related to the number of hydrophobic Py residues and the repeating Py-Arg building units of AMPs (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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Structure-Dependent Antimicrobial Theranostic Functions of Self-Assembled Short Peptide Nanoagents

et al. 2017

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Gadolinium (Gd[III])-based nanoaggregates are potential noninvasive magnetic resonance imaging (MRI) probes with excellent spatial and temporal resolution for cancer diagnosis. Peptides conjugated with Gd can aid in supramolecular scaffolding for MRI nanoagents because of their inherent biocompatibility and degradability. We report here a strategy to tune the MR relaxivity of tumor cell-targeted nanoagents and enhance the antimicrobial and anticancer activities of nanoagents based on rationally designed antimicrobial peptide (AMP) assembly. A tripeptide with glycyl-l-histidyl-l-lysine (GHK) capable of Gd chelation was attached to short AMPs containing pyrazole amino acids that spontaneously assembled as a function of the number of hydrophobic amino acid residues and the peptide length of AMPs. Aqueous coassembly of GHK with tumor-targeting, cyclic arginine-glycine-aspartic acid (cRGD)-tagged AMPs resulted in the formation of micelles, fibrils, vesicles, sheets, and planar networks. Interestingly, the two-dimensional planar network nanostructure showed less antibacterial activity and tumor cell cytotoxicity but greater drug loading/delivery and magnetic resonance signaling than micelles because of its intrinsic structural characteristics. This study can provide a rational approach for the design and fabrication of clinically useful nanoagents.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structure-Dependent Antimicrobial Theranostic Functions of Self-Assembled Short Peptide Nanoagents

et al. 2017

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“…Moreover, this result also demonstrated that the GHK‐Cu NPs could be more stable than the GHK‐Cu monomers and so they can have a better antibacterial performance at the same concentration. The previous studies have stated that the GHK‐Cu monomers are unstable in the biological fluids due to enzymatic degradation . Therefore, the self‐assembly process improves the stability and enhances the biological functions of the GHK‐Cu.…”

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confidence: 99%

Self‐Assembled Fluorescent and Antibacterial GHK‐Cu Nanoparticles for Wound Healing Applications

Sun

et al. 2019

Part & Part Syst Charact

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GHK‐Cu is demonstrated with the abilities to improve wound healing, accelerate anti‐inflammatory activity, and repair DNA damage. However, the instability of the GHK‐Cu in biological fluids is always a big challenge for its long‐term and efficient function at the target site. Therefore, the self‐assembled GHK‐Cu nanoparticles (GHK‐Cu NPs) are investigated in this work to solve the instability issue. The crystalline nanostructure within the GHK‐Cu nanoparticles offers them visible and near‐infrared fluorescent properties. With the excellent self‐assembly performance, the antibacterial properties of GHK‐Cu NPs are demonstrated using E. coli and S. aureus. The L929 dermal fibroblast cells are utilized to prove the good biocompatibility and enhanced wound healing applications of GHK‐Cu NPs. This study could pave the way for the design and elaboration of a new class of fluorescent peptides with various biological functions in biomedical applications.

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Synthesis of orthogonally protected azahistidine: application to the synthesis of a GHK analogue

et al. 2009

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A new synthesis of the tripeptide Gly-His-Lys with antimicrobial activity

Cited by 9 publications

References 14 publications

Structure-Dependent Antimicrobial Theranostic Functions of Self-Assembled Short Peptide Nanoagents

Structure-Dependent Antimicrobial Theranostic Functions of Self-Assembled Short Peptide Nanoagents

Self‐Assembled Fluorescent and Antibacterial GHK‐Cu Nanoparticles for Wound Healing Applications

Synthesis of orthogonally protected azahistidine: application to the synthesis of a GHK analogue

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