TY - JOUR
T1 - Cytotoxicity, alpha-glucosidase inhibition and molecular docking studies of hydroxamic acid chromium(III) complexes
AU - Hassan, Latifah Robbaniyyah
AU - Anouar, El Hassane
AU - Bahron, Hadariah
AU - Abdullah, Faiezah
AU - Mohd Tajuddin, Amalina
N1 - Publisher Copyright:
© 2020, Society for Biological Inorganic Chemistry (SBIC).
PY - 2020/3/1
Y1 - 2020/3/1
N2 - Hydroxamic acids [R(CO)N(OH)R’] are flexible compounds for organic and inorganic analyses due to their frailer structures compared to the carboxylic acid. The syntheses and characterization of benzohydroxamic acid (BHA), its CH3–, OCH3–, Cl– para-substituted derivatives and their Cr(III) complexes are reported herein. The metal complexes were synthesized by reacting the hydroxamic acids with chromium(III) chloride hexahydrate in 2:1 molar ratio. The compounds were characterized via melting point, elemental analysis, FTIR, 1H and 13C NMR, TGA, mass spectrometry, molar conductance and UV–Visible. Data analysis suggests that each complex has the Cr(III) center coordinated to the carbonyl and hydroxy oxygen atoms of the hydroxamic acids in bidentate O,O manner and two water molecules to form octahedral geometry. Non-electrolytic behavior of the complexes was shown through their low molar conductivity. Cytotoxicity study against HCT116 and alpha-glucosidase inhibition test revealed that all complexes have higher activity than their parent ligands. Molecular docking study shows that the docking of active complexes is thermodynamically favorable and the inhibition efficiency may depend on the types and the numbers of molecular interactions established in the corresponding stable conformers.
AB - Hydroxamic acids [R(CO)N(OH)R’] are flexible compounds for organic and inorganic analyses due to their frailer structures compared to the carboxylic acid. The syntheses and characterization of benzohydroxamic acid (BHA), its CH3–, OCH3–, Cl– para-substituted derivatives and their Cr(III) complexes are reported herein. The metal complexes were synthesized by reacting the hydroxamic acids with chromium(III) chloride hexahydrate in 2:1 molar ratio. The compounds were characterized via melting point, elemental analysis, FTIR, 1H and 13C NMR, TGA, mass spectrometry, molar conductance and UV–Visible. Data analysis suggests that each complex has the Cr(III) center coordinated to the carbonyl and hydroxy oxygen atoms of the hydroxamic acids in bidentate O,O manner and two water molecules to form octahedral geometry. Non-electrolytic behavior of the complexes was shown through their low molar conductivity. Cytotoxicity study against HCT116 and alpha-glucosidase inhibition test revealed that all complexes have higher activity than their parent ligands. Molecular docking study shows that the docking of active complexes is thermodynamically favorable and the inhibition efficiency may depend on the types and the numbers of molecular interactions established in the corresponding stable conformers.
KW - Alpha-glucosidase
KW - Benzohydroxamic acid
KW - Chromium(III)
KW - Cytotoxicity
KW - Molecular docking
UR - http://www.scopus.com/inward/record.url?scp=85078347361&partnerID=8YFLogxK
U2 - 10.1007/s00775-020-01755-6
DO - 10.1007/s00775-020-01755-6
M3 - Article
C2 - 31974764
AN - SCOPUS:85078347361
SN - 0949-8257
VL - 25
SP - 239
EP - 252
JO - Journal of Biological Inorganic Chemistry
JF - Journal of Biological Inorganic Chemistry
IS - 2
ER -