TY - JOUR
T1 - Synthesis, spectroscopic characterizations, carbonic anhydrase II inhibitory activity, anticancer activity and docking studies of new Schiff bases of sulfa drugs
AU - Alyar, Saliha
AU - Özmen, Ümmühan Özdemir
AU - Adem, Şevki
AU - Alyar, Hamit
AU - Bilen, Esra
AU - Kaya, Kerem
N1 - Publisher Copyright:
© 2020
PY - 2021/1/5
Y1 - 2021/1/5
N2 - Herein we present the synthesis, and biological evaluation of new Schiff bases incorporating (2‑hydroxy-5-methylbenzaldehyde sulfisoxazole (S2M-S1) and 2‑hydroxy-5-methylbenzaldehyde sulfamethoxazole (S1M-S1) derived from sulfisoxazole (S2)/sulfamethoxazole (S1) and substituted salicylaldehyde and their Pd (II), Cu(II) complexes. The synthesized compounds were characterized by FT-IR, 1H–13C NMR, LC-MS, magnetic susceptibility and conductivity measurements. The molecular structure of S2M-S1 was also determined by the single crystal X-ray diffraction technique and was found to crystallize in the monoclinic, space group P1 21/n 1. We investigated the effects of molecules on human carbonic anhydrase isoenzyme II (hCAII). Cu(S2M-S1)2, Pb(S2M-S1)2, Pb(S1M-S1)2, and Cu(S1M-S1)2, exhibited inhibitory effects with 10, 20, 42 and 67 µM IC50 value, respectively. Also, molecular Docking studies performed and anticancer activities of newly synthesized compounds were evaluated against three human cancer cell lines with the sulfonamide B test. S2M-S1, S1M-S1 compounds and their Cu (II) complexes exhibited promising cytotoxic activity against all cell lines. IC50 values for breast (MCF7) cells are 40 µM for S2M-S1, S1M-S1 compounds and their Cu (II) complexes.
AB - Herein we present the synthesis, and biological evaluation of new Schiff bases incorporating (2‑hydroxy-5-methylbenzaldehyde sulfisoxazole (S2M-S1) and 2‑hydroxy-5-methylbenzaldehyde sulfamethoxazole (S1M-S1) derived from sulfisoxazole (S2)/sulfamethoxazole (S1) and substituted salicylaldehyde and their Pd (II), Cu(II) complexes. The synthesized compounds were characterized by FT-IR, 1H–13C NMR, LC-MS, magnetic susceptibility and conductivity measurements. The molecular structure of S2M-S1 was also determined by the single crystal X-ray diffraction technique and was found to crystallize in the monoclinic, space group P1 21/n 1. We investigated the effects of molecules on human carbonic anhydrase isoenzyme II (hCAII). Cu(S2M-S1)2, Pb(S2M-S1)2, Pb(S1M-S1)2, and Cu(S1M-S1)2, exhibited inhibitory effects with 10, 20, 42 and 67 µM IC50 value, respectively. Also, molecular Docking studies performed and anticancer activities of newly synthesized compounds were evaluated against three human cancer cell lines with the sulfonamide B test. S2M-S1, S1M-S1 compounds and their Cu (II) complexes exhibited promising cytotoxic activity against all cell lines. IC50 values for breast (MCF7) cells are 40 µM for S2M-S1, S1M-S1 compounds and their Cu (II) complexes.
KW - Anticancer activity
KW - Cu(II)
KW - Docking study
KW - Enzyme inhibition
KW - Pd (II)
KW - Sulfamethoxazole
KW - Sulfisoxazole
UR - http://www.scopus.com/inward/record.url?scp=85088913187&partnerID=8YFLogxK
U2 - 10.1016/j.molstruc.2020.128911
DO - 10.1016/j.molstruc.2020.128911
M3 - Article
AN - SCOPUS:85088913187
SN - 0022-2860
VL - 1223
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
M1 - 128911
ER -
