Stability, Structure, and Permeability Studies of Copper Tripeptide Species in Aqueous Solution

Ahmed N. Hammouda; Fatin M. Elmagbari; Graham E. Jackson; Giselle M. Vicatos; Raffaele P. Bonomo; Gabriele Valora

doi:10.1071/ch21040

journal article Jun 22, 2021

Stability, Structure, and Permeability Studies of Copper Tripeptide Species in Aqueous Solution

Ahmed N. Hammouda

Fatin M. Elmagbari Graham E. Jackson

Giselle M. Vicatos Raffaele P. Bonomo

Gabriele Valora

Australian Journal of Chemistry Vol. 74 No. 8 pp. 613-622 · CSIRO Publishing

View at Publisher Save 10.1071/ch21040

Abstract

The use of copper complexes to alleviate inflammation associated with rheumatoid arthritis (RA) is well known. This study focuses on designing a new drug that could be used to increase the bioavailability of copper and hence be more effective. The ligand chosen was sarcosyl-l-lysyl-l-lysine (Sar-Lys-Lys). The thermodynamic stability of H+, CuII, NiII, and ZnII complexes of Sar-Lys-Lys was measured in an aqueous solution at 298 ± 0.01°C and an ionic strength of 0.15 M (NaCl) using glass electrode potentiometry. UV-Vis, ESR, and 1H NMR spectroscopy was used to investigate the solution structures of the different species. At physiological pH, the ligand was found to coordinate via two amide nitrogens, the terminal amine, and the terminal carboxy group. The ε-amino group of lysine did not coordinate with the metal ion. Dermal absorption is the preferred method of administration and so this study used partition coefficients and tissue permeability studies to assess the bioavailability of the different complexes. Sar-Lys-Lys was found to increase the copper lipophilicity by a factor of 10 and increased tissue permeability by 30 %.

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Details

Published: Jun 22, 2021
Vol/Issue: 74(8)
Pages: 613-622
License: View

Authors

A

Ahmed N. Hammouda

ADepartment of Chemistry, University of Cape Town, Rondebosch 7700, South Africa.; BDepartment of Chemistry, Faculty of Science, University of Benghazi, Qar Yunis, Benghazi, PO Box 9480, Libya.; DCorresponding author. Email: Ahmed.hammouda@uct.ac.za

F

Fatin M. Elmagbari

ADepartment of Chemistry, University of Cape Town, Rondebosch 7700, South Africa.; BDepartment of Chemistry, Faculty of Science, University of Benghazi, Qar Yunis, Benghazi, PO Box 9480, Libya.

G

Graham E. Jackson

ADepartment of Chemistry, University of Cape Town, Rondebosch 7700, South Africa.

G

Giselle M. Vicatos

ADepartment of Chemistry, University of Cape Town, Rondebosch 7700, South Africa.

R

Raffaele P. Bonomo

CDepartment of Chemical Sciences, University of Catania, Viale A. Doria 6, 95125, Italy.

G

Gabriele Valora

CDepartment of Chemical Sciences, University of Catania, Viale A. Doria 6, 95125, Italy.

Cite This Article

Ahmed N. Hammouda, Fatin M. Elmagbari, Graham E. Jackson, et al. (2021). Stability, Structure, and Permeability Studies of Copper Tripeptide Species in Aqueous Solution. Australian Journal of Chemistry, 74(8), 613-622. https://doi.org/10.1071/ch21040

Stability, Structure, and Permeability Studies of Copper Tripeptide Species in Aqueous Solution

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