Synthesis, characterization and anti-tubercular activities of copper(II) complexes of substituted 2,3-isatin bisthiosemicarbazones: An experimental and theoretical approach
Copper(II) acetate reacted with 2,3-isatin bisthiosemicarbazone (2,3 H2bitsc), 2,3-isatin bis-N1-methyl thiosemicarbazone (2,3 H2bitsc-N1-Me) and 2,3-isatin N1-phenyl thiosemicarbazone (2,3 H2bitsc-N1-Ph) in 1:1 (M: L) to form complexes of formula, [Cu(L)] (L = 2,3 bitsc 1, 2,3 bitsc-N1-Me 2, 2,3 bi...
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Elsevier
2023-12-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715623004101 |
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| author | Qurat Ul Ain Amandeep Singh Iqubal Singh Raanan Carmieli Rekha Sharma |
| author_facet | Qurat Ul Ain Amandeep Singh Iqubal Singh Raanan Carmieli Rekha Sharma |
| author_sort | Qurat Ul Ain |
| collection | DOAJ |
| description | Copper(II) acetate reacted with 2,3-isatin bisthiosemicarbazone (2,3 H2bitsc), 2,3-isatin bis-N1-methyl thiosemicarbazone (2,3 H2bitsc-N1-Me) and 2,3-isatin N1-phenyl thiosemicarbazone (2,3 H2bitsc-N1-Ph) in 1:1 (M: L) to form complexes of formula, [Cu(L)] (L = 2,3 bitsc 1, 2,3 bitsc-N1-Me 2, 2,3 bitsc-N1-Ph 3). The formation of bisthiosemicarbazone ligands and their complexes are supported by elemental analysis, FTIR, NMR (1H and 13C), ESR, and Mass. For complexes 1–3, two g values obtained are: g‖ = 2.24 (1), 2.17 (2), 2.26 (3) and g⊥ = 2.09 (1), 2.11 (2), 2.08 (3) which confirm axial symmetry. The square planar geometry is confirmed from higher g‖ values than g⊥ and presence g value of free electron in dx2-y2 ground term. Ligand to metal binding ratio of 1:1 is confirmed using UV–visible spectroscopy. The ligands (2,3 H2bitsc, 2,3 H2bitsc-N1-Me and 2,3 H2bitsc-N1-Ph) and complexes (1–3) were assessed for anti-tubercular (M. tuberculosis H37RV strain ATCC27294) and antibacterial (against E. coli and S. aureus) activities. The anti- tuberculosis activity of ligands (50 µg/mL-2,3 H2bitsc, 100 µg/mL-2,3 H2bitsc-N1-Me and H2bitsc-N1-Ph) gets enhanced on complexation with copper (25 µg /mL-1, 50 µg/mL 2 and 3). The minimal binding energies calculated through molecular modeling with mycobacterium tuberculosis enoyl reductase (PDB ID: 2H7M) is −7.6 (2,3 H2bitsc), −7.3 (2,3 H2bitsc-N1-Me), −9.6 (2,3 H2bitsc-N1-Ph), −8.7 (1), −8.9 (2), and −10.7 (3) Kcal/mol. Higher negative binding energy indicates more stabilized structure in the docked state for 1–3 which supports the experimental data. The drug-protein binding study with human serum albumin (HSA) was used to explore effective transport of molecules to their target sites in 2,3 H2bitsc and its complex 1. A high binding constant of complex 1 (6.09 × 105 M−1) with respect to the ligand 2,3 H2bitsc (4.90 × 105 M−1) indicates its strong binding affinities with HSA. |
| first_indexed | 2024-03-09T01:28:45Z |
| format | Article |
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| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-03-09T01:28:45Z |
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| spelling | doaj.art-d8be0d42cc3d4feab843b2968671383c2023-12-10T06:15:29ZengElsevierResults in Chemistry2211-71562023-12-016101171Synthesis, characterization and anti-tubercular activities of copper(II) complexes of substituted 2,3-isatin bisthiosemicarbazones: An experimental and theoretical approachQurat Ul Ain0Amandeep Singh1Iqubal Singh2Raanan Carmieli3Rekha Sharma4School of Chemical Engineering and Physical Sciences, Lovely Professional University, Punjab, IndiaSchool of Chemical Engineering and Physical Sciences, Lovely Professional University, Punjab, IndiaSchool of Pharmaceutical Science, Lovely Professional University, Punjab, IndiaDepartment of Chemical Research Support, Weizmann Institute of Science, Rehovot 76100, IsraelSchool of Chemical Engineering and Physical Sciences, Lovely Professional University, Punjab, India; Corresponding author.Copper(II) acetate reacted with 2,3-isatin bisthiosemicarbazone (2,3 H2bitsc), 2,3-isatin bis-N1-methyl thiosemicarbazone (2,3 H2bitsc-N1-Me) and 2,3-isatin N1-phenyl thiosemicarbazone (2,3 H2bitsc-N1-Ph) in 1:1 (M: L) to form complexes of formula, [Cu(L)] (L = 2,3 bitsc 1, 2,3 bitsc-N1-Me 2, 2,3 bitsc-N1-Ph 3). The formation of bisthiosemicarbazone ligands and their complexes are supported by elemental analysis, FTIR, NMR (1H and 13C), ESR, and Mass. For complexes 1–3, two g values obtained are: g‖ = 2.24 (1), 2.17 (2), 2.26 (3) and g⊥ = 2.09 (1), 2.11 (2), 2.08 (3) which confirm axial symmetry. The square planar geometry is confirmed from higher g‖ values than g⊥ and presence g value of free electron in dx2-y2 ground term. Ligand to metal binding ratio of 1:1 is confirmed using UV–visible spectroscopy. The ligands (2,3 H2bitsc, 2,3 H2bitsc-N1-Me and 2,3 H2bitsc-N1-Ph) and complexes (1–3) were assessed for anti-tubercular (M. tuberculosis H37RV strain ATCC27294) and antibacterial (against E. coli and S. aureus) activities. The anti- tuberculosis activity of ligands (50 µg/mL-2,3 H2bitsc, 100 µg/mL-2,3 H2bitsc-N1-Me and H2bitsc-N1-Ph) gets enhanced on complexation with copper (25 µg /mL-1, 50 µg/mL 2 and 3). The minimal binding energies calculated through molecular modeling with mycobacterium tuberculosis enoyl reductase (PDB ID: 2H7M) is −7.6 (2,3 H2bitsc), −7.3 (2,3 H2bitsc-N1-Me), −9.6 (2,3 H2bitsc-N1-Ph), −8.7 (1), −8.9 (2), and −10.7 (3) Kcal/mol. Higher negative binding energy indicates more stabilized structure in the docked state for 1–3 which supports the experimental data. The drug-protein binding study with human serum albumin (HSA) was used to explore effective transport of molecules to their target sites in 2,3 H2bitsc and its complex 1. A high binding constant of complex 1 (6.09 × 105 M−1) with respect to the ligand 2,3 H2bitsc (4.90 × 105 M−1) indicates its strong binding affinities with HSA.http://www.sciencedirect.com/science/article/pii/S2211715623004101IsatinBisthiosemicarbazone1HNMR13CNMRMetal complexesMass spectroscopy |
| spellingShingle | Qurat Ul Ain Amandeep Singh Iqubal Singh Raanan Carmieli Rekha Sharma Synthesis, characterization and anti-tubercular activities of copper(II) complexes of substituted 2,3-isatin bisthiosemicarbazones: An experimental and theoretical approach Results in Chemistry Isatin Bisthiosemicarbazone 1HNMR 13CNMR Metal complexes Mass spectroscopy |
| title | Synthesis, characterization and anti-tubercular activities of copper(II) complexes of substituted 2,3-isatin bisthiosemicarbazones: An experimental and theoretical approach |
| title_full | Synthesis, characterization and anti-tubercular activities of copper(II) complexes of substituted 2,3-isatin bisthiosemicarbazones: An experimental and theoretical approach |
| title_fullStr | Synthesis, characterization and anti-tubercular activities of copper(II) complexes of substituted 2,3-isatin bisthiosemicarbazones: An experimental and theoretical approach |
| title_full_unstemmed | Synthesis, characterization and anti-tubercular activities of copper(II) complexes of substituted 2,3-isatin bisthiosemicarbazones: An experimental and theoretical approach |
| title_short | Synthesis, characterization and anti-tubercular activities of copper(II) complexes of substituted 2,3-isatin bisthiosemicarbazones: An experimental and theoretical approach |
| title_sort | synthesis characterization and anti tubercular activities of copper ii complexes of substituted 2 3 isatin bisthiosemicarbazones an experimental and theoretical approach |
| topic | Isatin Bisthiosemicarbazone 1HNMR 13CNMR Metal complexes Mass spectroscopy |
| url | http://www.sciencedirect.com/science/article/pii/S2211715623004101 |
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