TY - JOUR
T1 - Casiopeinas® third generation, with indomethacin
T2 - synthesis, characterization, DFT studies, antiproliferative activity, and nanoencapsulation
AU - Godínez-Loyola, Yokari
AU - Gracia-Mora, Jesús
AU - Rojas-Montoya, Iván D
AU - Hernández-Ayala, Luis Felipe
AU - Reina, Miguel
AU - Ortiz-Frade, Luis Antonio
AU - Rascón-Valenzuela, Luisa Alondra
AU - Robles-Zepeda, Ramón Enrique
AU - Gómez-Vidales, Virginia
AU - Bernad-Bernad, María Josefa
AU - Ruiz-Azuara, Lena
N1 - This journal is © The Royal Society of Chemistry.
PY - 2022/7/21
Y1 - 2022/7/21
N2 - Seven new Casiopeinas® were synthesized and properly characterized. These novel compounds have a general formula [Cu(N-N)(
Indo)]NO
3, 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)]NO
3 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.
AB - Seven new Casiopeinas® were synthesized and properly characterized. These novel compounds have a general formula [Cu(N-N)(
Indo)]NO
3, 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)]NO
3 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.
U2 - 10.1039/d2ra03346a
DO - 10.1039/d2ra03346a
M3 - Artículo
C2 - 35975050
VL - 12
SP - 21662
EP - 21673
JO - RSC Advances
JF - RSC Advances
SN - 2046-2069
IS - 33
ER -