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.
Highlights
Benzothiazoles are a class of bicyclic compounds with a broad spectrum of biological applications such as neuroprotective effects [1,2], antimicrobial activity [3,4,5,6], antioxidant and radioprotective effects [7], anticonvulsant activity [8,9] and antitumor properties [10,11]
The second dimension is developed by weak interactions C16—H16A∙∙∙Ph between the participation of a methyl hydrogen from the methoxy group, as the donor, and the centroid of the helixes, through the participation of a methyl hydrogen from the methoxy group, as the donor, and hydroxymethoxyphenyl ring, as the acceptor.ring, Details of the geometry of theofhydrogen bonding are the centroid of the hydroxymethoxyphenyl as the acceptor
50 = 4.02 μM, determined in an exposure) [17]. These results show a similar behavior to other cell lines because we did not observe a assay after 96 of cells, exposure)
Summary
Benzothiazoles are a class of bicyclic compounds with a broad spectrum of biological applications such as neuroprotective effects [1,2], antimicrobial activity [3,4,5,6], antioxidant and radioprotective effects [7], anticonvulsant activity [8,9] and antitumor properties [10,11]. Recent studies showed that this compound and its analogues promote signaling and nuclear translocation of Aryl hydrocarbon Receptor (AhR) and induce the carboxyl terminus of Hsp70-interacting protein (CHIP) expression through recruitment of AhR upstream of the CHIP gene. This mechanism has potential application in the suppression of tumor progression in breast cancer cells [13,14,15,16,17]. 2-(4-hydroxy-3-methoxyphenyl)-benzothiazole was synthetized, crystalized, and its molecular X-ray structure was compared with that simulated by theoretical calculations. Its activity on cervical cancer cell line (HeLa) was evaluated
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