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Crystals 2017, 7(6), 171; doi:10.3390/cryst7060171

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

1
Laboratorio de Investigación en Bioquímica, Escuela Superior de Medicina, Instituto Politécnico Nacional, Plan de San Luis y Díaz Mirón s/n Casco de Santo Tomás, Mexico City 11340, Mexico
2
Laboratorio de Química Supramolecular y Nanociencias, Instituto Politécnico Nacional-UPIBI, Av. Acueducto s/n Barrio la Laguna Ticomán, Ciudad de México C.P. 07340, Mexico
*
Author to whom correspondence should be addressed.
Academic Editor: Sławomir J. Grabowski
Received: 3 May 2017 / Revised: 2 June 2017 / Accepted: 7 June 2017 / Published: 11 June 2017
(This article belongs to the Section Interactions in Crystal Structures)
View Full-Text   |   Download PDF [1816 KB, uploaded 11 June 2017]   |  

Abstract

Benzothiazoles are a set of molecules with a broad spectrum of biological applications. In particular, 2-(4-hydroxy-3-methoxyphenyl)-benzothiazole is a potential breast cancer cell suppressor whose mechanism of action has been previously reported. In the present work, the title compound was synthesized, crystallized, and its biological activity on HeLa cells was evaluated. Its molecular structure was compared to that obtained by molecular modeling. Theoretical calculations suggest that the syn-rotamer is the most stable form and correlates very well with crystallographic data. The crystal structure adopts a helical arrangement formed through O13—H13∙∙∙N3 intermolecular hydrogen bonding that propagates in the (14 -1 -3) plane. These results suggest that the title compound has the capacity to interleave into DNA and better explain its biological effects related to the increased CHIP expression through AhR recruitment. Finally, the biological experiments indicate that the title compound has the capacity to decrease the viability of HeLa cells with an IC50 = 2.86 μM. View Full-Text
Keywords: helical arrangement of benzothiazole; rotational energy properties; HeLa cells helical arrangement of benzothiazole; rotational energy properties; HeLa cells
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Cuevas-Hernández, R.I.; Padilla-Martínez, I.I.; Martínez-Cerón, S.; Vásquez-Moctezuma, I.; Trujillo-Ferrara, J.G. Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells. Crystals 2017, 7, 171.

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