Synthesis of chalcones with antiproliferative activity on the SH-SY5Y neuroblastoma cell line: Quantitative Structure–Activity Relationship Models

Marco Mellado, Alejandro Madrid, Mauricio Reyna, Caroline Weinstein-Oppenheimer, Jaime Mella, Cristian O. Salas, Elizabeth Sánchez, Mauricio Cuellar

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

26 Citas (Scopus)

Resumen

Chalcones are a group of molecules with a broad spectrum of biological activities, being especially appealing for their antiproliferative effects on several cancer cell lines. For this reason, we synthesized 23 chalcones with good to excellent yields and assessed their effect on the viability of the SH-SY5Y neuroblastoma cell line and on primary human fibroblasts. The results indicated that 18 of these compounds were more active than 5-fluorouracil in the cancer cell line and one of them was more selective than this reference drug. To identify structural features related to the antiproliferative activity of these compounds, as well as, the selectivity on the cancer cell line, a 2D-QSAR analysis was performed. The QSAR model (q2 = 0.803; r2 = 0.836) showed that lipophilicity (CLogP) is the most important factor to increase their cytotoxicity on the cancer cell line. On the other hand, the selectivity QSAR model (q2 = 0.917; r2 = 0.916) showed that changes in the Mulliken’s charge of the carbonyl group and at the C4’ position in the chalcone core can increase the selectivity for SH-SY5Y cell line compared to normal fibroblasts.

Idioma originalInglés
Páginas (desde-hasta)2414-2425
Número de páginas12
PublicaciónMedicinal Chemistry Research
Volumen27
N.º11-12
DOI
EstadoPublicada - 1 dic. 2018
Publicado de forma externa

Huella

Profundice en los temas de investigación de 'Synthesis of chalcones with antiproliferative activity on the SH-SY5Y neuroblastoma cell line: Quantitative Structure–Activity Relationship Models'. En conjunto forman una huella única.

Citar esto