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Synthesis and cytotoxic evaluation of halogenated furanones

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Abstract

The objective of the current study is to evaluate the potency of halogen-furan-2(5H)-one-type derivatives against human cancer cell lines. Four known bromofuran-2(5H)-one-type derivatives, as well as five new and two known bromo-4-(phenylamino)furan-2(5H)-one-type compounds and six novel and two known halogen-4-alkyl-5-phenyl-3-(phenylamino)furan-2(5H)-one-type derivatives, were synthesized and evaluated for their anticancer activity against prostate (PC-3) and colon (HCT-116) human cancer cell lines. The results showed that only the bromofuran-2(5H)-ones were cytotoxic in both cell lines. Three of these displayed particularly useful antiproliferative activities, in both cancer cells evaluated. (E)-5-(Bromomethylene)furan-2-(5H)-one was the most active against PC-3 (IC50 0.93 ± 0.02 μM) while 3,4-dibromofuran-2(5H)-one was the most active against HCT-116 (IC50 0.4 ± 0.04 μM). Furthermore, flow cytometry studies revealed that the bromofuran-2(5H)-ones induced cell death by apoptosis. Also, it was found that the cytotoxic furanones induced lipid peroxidation, determined by TBARS assay. Thus, cytotoxicity of the active compounds could be associated with ROS production. Additionally, it must be taken into account that all cytotoxic compounds contain an electrophilic carbon atom in position 4, which can explain, through a non-specific reactivity with nucleophiles, the cytotoxic activity of these compounds.

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Acknowledgements

Víctor A. Castro-Torres is a doctoral student from the Programa de Doctorado en Ciencias Biomédicas, Universidad Nacional Autónoma de México (UNAM) and has received CONACyT fellowship 267787. This study was supported by Grants from PAPIIT IN211819 and CONACyT 402838 and 00042. We acknowledge the technical support of MS Antonio Nieto-Camacho and MS María Teresa O. Ramírez-Apan from Instituto de Química-UNAM.

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Authors and Affiliations

  1. Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Circuito Exterior S/N Circuito Exterior, C.U., Coyoacán, 04510, Mexico City, Mexico

    Víctor A. Castro-Torres, Lidia Díaz-Sánchez & Mariano Martínez-Vázquez

  2. Unidad de Bioquímica, Instituto Nacional de Ciencias Médicas y Nutrición Salvador Zubirán, Vasco de Quiroga 15, Belisario Domínguez Secc 16, Tlalpan, 14080, Mexico City, Mexico

    Nadia J. Jacobo-Herrera

  3. Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México (UNAM), Circuito, Mario de La Cueva s/n, C.U., Coyoacán, 04510, Mexico City, Mexico

    Leticia Rocha-Zavaleta

  4. Instituto Nacional de Cancerología, Av. San Fernando 22, Belisario Domínguez Secc 16, Tlalpan, 14080, Mexico City, Mexico

    Patricia García-López

Authors
  1. Víctor A. Castro-Torres
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  2. Nadia J. Jacobo-Herrera
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  3. Lidia Díaz-Sánchez
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  4. Leticia Rocha-Zavaleta
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  5. Patricia García-López
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  6. Mariano Martínez-Vázquez
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Correspondence to Nadia J. Jacobo-Herrera or Mariano Martínez-Vázquez.

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Castro-Torres, V.A., Jacobo-Herrera, N.J., Díaz-Sánchez, L. et al. Synthesis and cytotoxic evaluation of halogenated furanones. Monatsh Chem 151, 1841–1849 (2020). https://doi.org/10.1007/s00706-020-02708-0

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  • DOI: https://doi.org/10.1007/s00706-020-02708-0

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