TY - JOUR
T1 - Helical arrangement of 2-(4-hydroxy-3-methoxyphenyl)-benzothiazole in crystal formation and biological evaluation on HeLa cells
AU - Cuevas-Hernández, Roberto I.
AU - Padilla-Martínez, Itzia I.
AU - Martínez-Cerón, Sarai
AU - Vásquez-Moctezuma, Ismael
AU - Trujillo-Ferrara, José G.
N1 - Publisher Copyright:
© 2017 by the authors. Licensee MDPI, Basel, Switzerland.
PY - 2017/6/11
Y1 - 2017/6/11
N2 - 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.
AB - 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.
KW - HeLa cells
KW - Helical arrangement of benzothiazole
KW - Rotational energy properties
UR - http://www.scopus.com/inward/record.url?scp=85020883045&partnerID=8YFLogxK
U2 - 10.3390/cryst7060171
DO - 10.3390/cryst7060171
M3 - Artículo
AN - SCOPUS:85020883045
SN - 2073-4352
VL - 7
JO - Crystals
JF - Crystals
IS - 6
M1 - 171
ER -