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Biological Evaluation in Vitro and in Silico of Azetidin-2-one Derivatives as Potential Anticancer Agents
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    Biological Evaluation in Vitro and in Silico of Azetidin-2-one Derivatives as Potential Anticancer Agents
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    Universidad Autonoma de Nuevo Leon, Facultad de Ciencias Químicas, Monterrey, México
    Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Reynosa, México
    § Red de Estudios Moleculares Avanzados, Instituto de Ecología, A.C., Xalapa Enríquez, México
    *Tel: +52 81 83294000, ext 3435. Fax: +52 81 83529025. E-mail: [email protected]
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    ACS Medicinal Chemistry Letters

    Cite this: ACS Med. Chem. Lett. 2017, 8, 1, 32–37
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    https://doi.org/10.1021/acsmedchemlett.6b00313
    Published November 10, 2016
    Copyright © 2016 American Chemical Society

    Abstract

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    Potential anticancer activity of 16 azetidin-2-one derivatives was evaluated showing that compound 6 [N-(p-methoxy-phenyl)-2-(p-methyl-phenyl)-3-phenoxy-azetidin-2-one] presented cytotoxic activity in SiHa cells and B16F10 cells. The caspase-3 assay in B16F10 cells displayed that azetidin-2-one derivatives induce apoptosis. Microarray and molecular analysis showed that compound 6 was involved on specific gene overexpression of cytoskeleton regulation and apoptosis due to the inhibition of some cell cycle genes. From the 16 derivatives, compound 6 showed the highest selectivity to neoplastic cells, it was an inducer of apoptosis, and according to an in silico analysis of chemical interactions with colchicine binding site of human α/β-tubulin, the mechanism of action could be a molecular interaction involving the amino acids outlining such binding site.

    Copyright © 2016 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acsmedchemlett.6b00313.

    • Database deposition file with the accession number E-MTAB-4351 in the ArrayExpress electronic platform; 1H NMR and IR spectral data; elemental analysis data; three tables enlisting the group of altered genes by compound 6 in cell line B16F10 involved in cell death pathway; synthesis of the cytoskeleton and cell division processes (PDF)

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    This article is cited by 3 publications.

    1. Adarsh Kumar, Ankit Kumar Singh, Harshwardhan Singh, Veena Vijayan, Deepak Kumar, Jashwanth Naik, Suresh Thareja, Jagat Pal Yadav, Prateek Pathak, Maria Grishina, Amita Verma, Habibullah Khalilullah, Mariusz Jaremko, Abdul-Hamid Emwas, Pradeep Kumar. Nitrogen Containing Heterocycles as Anticancer Agents: A Medicinal Chemistry Perspective. Pharmaceuticals 2023, 16 (2) , 299. https://doi.org/10.3390/ph16020299
    2. Mohammad Nadeem Lone, Zubaid‐ul‐khazir, Ghulam Nabi Yatoo, Javid A. Banday, Irshad A. Wani. Recent Advances in Gold Complexes as Anticancer Agents. 2020, 247-271. https://doi.org/10.1002/9781119640868.ch8
    3. Ligia S. da Silveira Pinto, Thatyana R. Alves Vasconcelos, Claudia Regina B. Gomes, Marcus Vinícius N. de Souza. A Brief Review on the Development of Novel Potentially Active Azetidin-2-ones Against Cancer. Current Organic Chemistry 2020, 24 (5) , 473-486. https://doi.org/10.2174/1385272824666200303115444

    ACS Medicinal Chemistry Letters

    Cite this: ACS Med. Chem. Lett. 2017, 8, 1, 32–37
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acsmedchemlett.6b00313
    Published November 10, 2016
    Copyright © 2016 American Chemical Society

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