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


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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.

About the authors

Ixamail Fraire-Soto

Laboratorio de MicroRNAs y Cáncer, Universidad Autónoma de Zacatecas, Av. Preparatoria S/N

Email: info@benthamscience.net

Jorge Araujo-Huitrado

Laboratorio de MicroRNAs y Cáncer,, Universidad Autónoma de Zacatecas, Av. Preparatoria S/N

Email: info@benthamscience.net

Angelica Granados-López

Laboratorio de MicroRNAs y Cáncer, Universidad Autónoma de Zacatecas, Av. Preparatoria S/N

Email: info@benthamscience.net

Luis Segura-Quezada

Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato, División de Ciencias Naturales y Exactas

Email: info@benthamscience.net

Rafael Ortiz-Alvarado

Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato

Email: info@benthamscience.net

Mayra Herrera

Laboratorio de MicroRNAs y Cáncer, Universidad Autónoma de Zacatecas, Av. Preparatoria S/N

Email: info@benthamscience.net

Rosalinda Gutiérrez-Hernández

Laboratorio de MicroRNAs y Cáncer, Universidad Autónoma de Zacatecas

Email: info@benthamscience.net

Claudia Reyes-Hernández

Laboratorio de MicroRNAs y Cáncer, Universidad Autónoma de Zacatecas, Av. Preparatoria S/N

Email: info@benthamscience.net

Yamilé López-Hernández

, Laboratorio de Metabolómica y Proteómica Universidad Autónoma de Zacatecas

Email: info@benthamscience.net

Melissa Tapia-Juárez

Laboratorio de Diseño Molecular, Instituto de Investigaciones Químico Biológicas,, Universidad Michoacana de San Nicolás de Hidalgo, Ciudad Universitaria

Email: info@benthamscience.net

José Negrete-Díaz

Laboratory of Brain Plasticity and Integrative Neuroscience, Program of Clinical Psychology, University of Guanajuato

Email: info@benthamscience.net

Luis Chacón-García

Laboratorio de Diseño Molecular, Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Ciudad Universitaria

Author for correspondence.
Email: info@benthamscience.net

César Solorio-Alvarado

Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Campus Guanajuato

Author for correspondence.
Email: info@benthamscience.net

Jesús López

Laboratorio de MicroRNAs y Cáncer, Universidad Autónoma de Zacatecas, Av. Preparatoria S/N

Author for correspondence.
Email: info@benthamscience.net

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