Differential Effect of 4H-Benzo[d] [1, 3]oxazines on the Proliferation of Breast Cancer Cell Lines-Reference-Cited by-同舟云学术

Differential Effect of 4H-Benzo[d] [1, 3]oxazines on the Proliferation of Breast Cancer Cell Lines

Published:2024-11 Issue:38 Volume:31 Page:6306-6318
ISSN:0929-8673
Container-title:Current Medicinal Chemistry
language:en
Short-container-title:CMC

Author:

Fraire-Soto Ixamail¹,Araujo-Huitrado Jorge Gustavo¹,Granados-López Angelica Judith¹,Segura-Quezada Luis A.²,Ortiz-Alvarado Rafael³,Herrera Mayra Denise¹⁴,Gutiérrez-Hernández Rosalinda¹,Reyes-Hernández Claudia Araceli⁵,López-Hernández Yamilé⁶,Tapia-Juárez Melissa⁷,Negrete-Díaz José Vicente⁸,Chacón-García Luis⁷,Solorio-Alvarado César R.³,López Jesús Adrián¹^ORCID

Affiliation:

1. Laboratorio de MicroRNAs y Cáncer, Universidad Autónoma de Zacatecas, Av. Preparatoria S/N, Agronómica, Campus II, Zacatecas, Zac., 98066, México

2. Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato, Noria Alta S/N, Guanajuato, 36050, México

3. Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato, Noria Alta S/N, Guanajuato, 36050, México

4. Campo Experimental Zacatecas (CEZAC-INIFAP), Carretera Zacatecas-Fresnillo Km 24.5, Calera de VR, Zacatecas, 98500, Mexico

5. Laboratorio de MicroRNAs y Cáncer, Universidad Autónoma de Zacatecas, Av. Preparatoria S/N, Agronómica, Campus II, Zacatecas, Zac., 98066, México;

6. Laboratorio de Metabolómica y Proteómica Universidad Autónoma de Zacatecas, Av. Preparatoria S/N, Agronómica, Campus II, Zacatecas, Zac., 98066, México

7. Laboratorio de Diseño Molecular, Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Ciudad Universitaria, Morelia, Mich., 58033, México

8. Laboratory of Brain Plasticity and Integrative Neuroscience, Program of Clinical Psychology, University of Guanajuato, Guanajuato, 38060, México

Abstract

Background: A family of 4H-benzo[d][1,3]oxazines were obtained from a group of N-(2-alkynyl)aryl benzamides precursors via gold(I) catalysed chemoselective 6-exo-dig C-O cyclization. Methods: The precursors and oxazines obtained were studied in breast cancer cell lines MCF-7, CAMA-1, HCC1954 and SKBR-3 with differential biological activity showing various degrees of inhibition with a notable effect for those that had an aryl substituted at C-2 of the molecules. 4H-benzo[d][1,3]oxazines showed an IC50 rating from 0.30 to 157.4 µM in MCF-7, 0.16 to 139 in CAMA-1, 0.09 to 93.08 in SKBR-3, and 0.51 to 157.2 in HCC1954 cells. Results: We observed that etoposide is similar to benzoxazines while taxol effect is more potent. Four cell lines responded to benzoxazines while SKBR-3 cell line responded to precursors and benzoxazines. Compounds 16, 24, 25 and 26 have the potent effect in cell proliferation inhibition in the 4 cell lines tested and correlated with oxidant activity suggesting a possible mechanism by ROS generation. Conclusion: These compounds represent possible drug candidates for the treatment of breast cancer. However, further trials are needed to elucidate its full effect on cellular and molecular features of cancer.

Publisher

Bentham Science Publishers Ltd.