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Article

Alteration of Anticancer and Protein-Binding Properties of Gold(I) Alkynyl by Phenolic Schiff Bases Moieties

1
Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
2
Chemistry Department, Deanship of Scientific Research, College of Sciences, Taif University, Al-Haweiah, P.O. Box 11099, Taif 21944, Saudi Arabia
3
Department of Chemistry, College of Science and Arts, King Abdulaziz University, P.O. Box 344, Rabigh 21911, Saudi Arabia
4
Core Labs, King Abdullah University of Science and Technology (KAUST), P.O. Box 4700, Thuwal 23955-6900, Saudi Arabia
5
Biological and Environmental Science and Engineering (BESE), King Abdullah University of Science and Technology (KAUST), P.O. Box 4700, Thuwal 23955-6900, Saudi Arabia
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Department of Chemistry, Faculty of Science, Port Said University, Port Said 42521, Egypt
*
Authors to whom correspondence should be addressed.
These authors contributed equally.
Academic Editors: Elena Cerrada and Vanesa Fernández-Moreira
Pharmaceutics 2021, 13(4), 461; https://doi.org/10.3390/pharmaceutics13040461
Received: 3 March 2021 / Revised: 17 March 2021 / Accepted: 18 March 2021 / Published: 29 March 2021
(This article belongs to the Special Issue Metallodrugs for Targeted Cancer Therapy)
A set of five gold complexes with the general formula Au(PR3)(C≡C-C6H4-4-R′) (R = PPh3, R′ = –CHO (1), R = PCy3, R′ = –CHO (2), R = PPh3, R′ = –N=CH-C6H4-2-OH (3), R = PPh3, R′ = –N=CH-C6H4-4-OH (4), R = PCy3, R′ = –N=CH-C6H4-2-OH (5)) were synthesized and characterized by elemental analysis, 1H-NMR spectroscopy, 31P-NMR spectroscopy, and mass spectrometry. The structures of complexes 2 and 5 were determined by X-ray crystallography. The effects of the structural modifications on the protein binding affinities and anticancer activities of the five gold complexes were assessed. Fluorescence quenching experiments to assess binding to human serum albumin (HSA) revealed that the Schiff base complexes (3, 4, and 5) had binding constants that were superior to their parent aldehyde complexes and highlighted the position of the hydroxy group because complex 4 (4-hydroxy) had a binding constant 6400 times higher than complex 3 (2-hydroxy). The anticancer activities of the complexes against the OVCAR-3 (ovarian carcinoma) and HOP-62 (non-small-cell lung) cancer cell lines showed that the Schiff bases (3–5) were more cytotoxic than the aldehyde-containing complexes (1 and 2). Notably, compound 4 had cytotoxic activity comparable to that of cisplatin against OVCAR-3, demonstrating the significance of the para position for the hydroxy group. Molecular docking studies against the enzyme thioredoxin reductase (TrxR) and human serum albumin were conducted, with docking scores in good agreement with the experimental data. The current study highlights how small structural modifications can alter physiochemical and anticancer properties. Moreover, this simple design strategy using the aldehyde group can generate extensive opportunities to explore new gold(I)-based anticancer drugs via condensation, cyclization, or nucleophilic addition reactions of the aldehyde. View Full-Text
Keywords: gold(I); phosphine; HSA-binding; molecular docking; anticancer properties gold(I); phosphine; HSA-binding; molecular docking; anticancer properties
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MDPI and ACS Style

Babgi, B.A.; Alsayari, J.; Alenezi, H.M.; Abdellatif, M.H.; Eltayeb, N.E.; Emwas, A.-H.M.; Jaremko, M.; Hussien, M.A. Alteration of Anticancer and Protein-Binding Properties of Gold(I) Alkynyl by Phenolic Schiff Bases Moieties. Pharmaceutics 2021, 13, 461. https://doi.org/10.3390/pharmaceutics13040461

AMA Style

Babgi BA, Alsayari J, Alenezi HM, Abdellatif MH, Eltayeb NE, Emwas A-HM, Jaremko M, Hussien MA. Alteration of Anticancer and Protein-Binding Properties of Gold(I) Alkynyl by Phenolic Schiff Bases Moieties. Pharmaceutics. 2021; 13(4):461. https://doi.org/10.3390/pharmaceutics13040461

Chicago/Turabian Style

Babgi, Bandar A., Jalal Alsayari, Hana M. Alenezi, Magda H. Abdellatif, Naser E. Eltayeb, Abdul-Hamid M. Emwas, Mariusz Jaremko, and Mostafa A. Hussien 2021. "Alteration of Anticancer and Protein-Binding Properties of Gold(I) Alkynyl by Phenolic Schiff Bases Moieties" Pharmaceutics 13, no. 4: 461. https://doi.org/10.3390/pharmaceutics13040461

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