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Synthesis, characterisation, and antineoplastic cytotoxicity of hybrid naphthohydroquinone–nucleic base mimic derivatives

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Abstract

From a partially degraded Diels–Alder adduct of α-myrcene and 1,4-benzoquinone, several model compounds belonging to a new series of 1,4-naphthohydroquinone derivatives have been prepared. Phenyl, pyridyl, imidazolyl and some nucleic base mimic heterocycles have been attached to the naphthohydroquinone system through linkers of different size and type, leading to potentially antineoplastic hybrid structures. The new compounds have been evaluated in vitro for their cytotoxicity against cultured human cancer cells of A-549 lung carcinoma, HT-29 colon adenocarcinoma and MDA-MB-231 breast carcinoma. GI50 values ranged in the μM level.

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Acknowledgements

The authors acknowledge the financial support from the Comisión Nacional de Investigación Científica y Tecnológica, CONICYT (Proyecto FONDECYT 1060447), Dirección de Investigación de la Vicerrectoría de Investigación y Estudios Avanzados de la Pontificia Universidad Católica de Valparaíso, Chile (Projects DI. 125.795-05 and 125.796-06), and Junta de Castilla y León, Spain (Project SA114A06). C. Ojeda acknowledges financial support from the Programa Mecesup, Project UCH 0408 for a research stay at the University of Salamanca, Spain. This research was performed under the auspices of the “Programa Iberoamericano CYTED - Subprograma X”.

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Authors and Affiliations

  1. Instituto de Química, Pontificia Universidad Católica de Valparaíso, Casilla 4059, Valparaiso, Chile

    Aurora Molinari, Claudia Ojeda & Alfonso Oliva

  2. Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, Salamanca, Spain

    José M. Miguel del Corral, M. Angeles Castro, Pablo A. García & Arturo San Feliciano

  3. PharmaMar S.A., Avda de los Reyes, P.I. La Mina Norte, 28770-Colmenar Viejo, Madrid, Spain

    Carmen Cuevas

Authors
  1. Aurora Molinari
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  2. Claudia Ojeda
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  3. Alfonso Oliva
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  4. José M. Miguel del Corral
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  5. M. Angeles Castro
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  6. Pablo A. García
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  7. Carmen Cuevas
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  8. Arturo San Feliciano
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Correspondence to Aurora Molinari.

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Molinari, A., Ojeda, C., Oliva, A. et al. Synthesis, characterisation, and antineoplastic cytotoxicity of hybrid naphthohydroquinone–nucleic base mimic derivatives. Med Chem Res 18, 59–69 (2009). https://doi.org/10.1007/s00044-008-9108-1

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  • DOI: https://doi.org/10.1007/s00044-008-9108-1

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