Casiopeinas® third generation, with indomethacin: synthesis, characterization, DFT studies, antiproliferative activity, and nanoencapsulation

Yokari Godínez-Loyola, Jesús Gracia-Mora, Iván D. Rojas-Montoya, Luis Felipe Hernández-Ayala, Miguel Reina, Luis Antonio Ortiz-Frade, Luisa Alondra Rascón-Valenzuela, Ramón Enrique Robles-Zepeda, Virginia Gómez-Vidales, María Josefa Bernad-Bernad*, Lena Ruiz-Azuara

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Seven new Casiopeinas® were synthesized and properly characterized. These novel compounds have a general formula [Cu(N-N)(Indo)]NO3, where Indo is deprotonated indomethacin and N-N is either bipyridine or phenanthroline with some methyl-substituted derivatives, belonging to the third generation of Casiopeinas®. Spectroscopic characterization suggests a square-based pyramid geometry and voltammetry experiments indicate that the redox potential is strongly dependent on the N-N ligand. All the presented compounds show high cytotoxic efficiency, and most of them exhibit higher efficacy compared to the well-known cisplatin drug and acetylacetonate analogs of the first generation. Computational calculations show that antiproliferative behavior can be directly related to the volume of the molecules. Besides, a chitosan (CS)-polyacrylamide (PNIPAAm) nanogel was synthesized and characterized to examine the encapsulation and release properties of the [Cu(4,7-dimethyl-1,10-phenanthroline)(Indo)]NO3 compound. The results show good encapsulation performance in acidic conditions and a higher kinetic drug release in acidic media than at neutral pH. This result can be described by the Peppas-Sahlin model and indicates a release mechanism predominantly by Fick diffusion.

Original languageEnglish
Pages (from-to)21662-21673
Number of pages12
JournalRSC Advances
Volume12
Issue number33
DOIs
StatePublished - 3 Aug 2022
Externally publishedYes

Bibliographical note

Funding Information:
The authors thank the projects of CONACyT Thematic Network 294727 (Farmoquímicos). Y. G. L. (grant 604136) L. F. H. A. (grant 307725). MR thanks UNAM-DGTIC for LANCAD-UNAM-DGTIC-410. The authors gratefully acknowledge Cedric Reyes Cadena, M. in C. Virginia Gomez Vidales, M. in C. Adrián Espinoza-Guillén, Dr Ernesto Rivera García for the computational and technical support to obtain EPR and SEM studies, respectively.

Publisher Copyright:
© 2022 The Royal Society of Chemistry.

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