Cargando…
Synthesis, DNA binding and biological evaluation of benzimidazole Schiff base ligands and their metal(ii) complexes
Two novel benzimidazole ligands (E)-2-((4-(1H-benzo[d]imidazole-2-yl)phenylimino)methyl)-6-bromo-4-chlorophenol (L(1)) and (E)-1-((4-(1H-benzo[d]imidazole-2-yl)phenylimino)methyl)naphthalene-2-ol (L(2)) with their corresponding Cu(ii), Ni(ii), Pd(ii) and Zn(ii) complexes were designed and synthesize...
Autores principales: | , , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107730/ https://www.ncbi.nlm.nih.gov/pubmed/37077261 http://dx.doi.org/10.1039/d3ra00982c |
_version_ | 1785026670160248832 |
---|---|
author | Mahmood, Khalid Akhter, Zareen Perveen, Fouzia Aisha, Bibi, Muneeba Ismail, Hammad Tabassum, Nida Yousuf, Sammer Ashraf, Ahmad Raza Qayyum, Muhammad Abdul |
author_facet | Mahmood, Khalid Akhter, Zareen Perveen, Fouzia Aisha, Bibi, Muneeba Ismail, Hammad Tabassum, Nida Yousuf, Sammer Ashraf, Ahmad Raza Qayyum, Muhammad Abdul |
author_sort | Mahmood, Khalid |
collection | PubMed |
description | Two novel benzimidazole ligands (E)-2-((4-(1H-benzo[d]imidazole-2-yl)phenylimino)methyl)-6-bromo-4-chlorophenol (L(1)) and (E)-1-((4-(1H-benzo[d]imidazole-2-yl)phenylimino)methyl)naphthalene-2-ol (L(2)) with their corresponding Cu(ii), Ni(ii), Pd(ii) and Zn(ii) complexes were designed and synthesized. The compounds were characterized by elemental, IR, and NMR ((1)H & (13)C) spectral analyses. Molecular masses were determined by ESI-mass spectrometry, and the structure of ligand L(1) was confirmed by single crystal X-ray diffraction analysis. Molecular docking was carried out for the theoretical investigation of DNA binding interactions. The results obtained were verified experimentally by UV/Visible absorption spectroscopy in conjunction with DNA thermal denaturation studies. It was observed that ligands (L(1) and L(2)) and complexes (1–8) were moderate to strong DNA binders, as evident from the binding constants (K(b)). The value was found to be highest for complex 2 (3.27 × 10(5) M(−1)) and lowest for 5 (6.40 × 10(3) M(−1)). A cell line study revealed that breast cancer cells were less viable to the synthesized compounds compared to that of standard drugs, cisplatin and doxorubicin, at the same concentration. The compounds were also screened for in vitro antibacterial activity for which complex 2 showed a promising broad-spectrum effect against all tested strains of bacteria, almost in the proximity of the reference drug kanamycin, while the rest of the compounds displayed activity against selected strains. |
format | Online Article Text |
id | pubmed-10107730 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-101077302023-04-18 Synthesis, DNA binding and biological evaluation of benzimidazole Schiff base ligands and their metal(ii) complexes Mahmood, Khalid Akhter, Zareen Perveen, Fouzia Aisha, Bibi, Muneeba Ismail, Hammad Tabassum, Nida Yousuf, Sammer Ashraf, Ahmad Raza Qayyum, Muhammad Abdul RSC Adv Chemistry Two novel benzimidazole ligands (E)-2-((4-(1H-benzo[d]imidazole-2-yl)phenylimino)methyl)-6-bromo-4-chlorophenol (L(1)) and (E)-1-((4-(1H-benzo[d]imidazole-2-yl)phenylimino)methyl)naphthalene-2-ol (L(2)) with their corresponding Cu(ii), Ni(ii), Pd(ii) and Zn(ii) complexes were designed and synthesized. The compounds were characterized by elemental, IR, and NMR ((1)H & (13)C) spectral analyses. Molecular masses were determined by ESI-mass spectrometry, and the structure of ligand L(1) was confirmed by single crystal X-ray diffraction analysis. Molecular docking was carried out for the theoretical investigation of DNA binding interactions. The results obtained were verified experimentally by UV/Visible absorption spectroscopy in conjunction with DNA thermal denaturation studies. It was observed that ligands (L(1) and L(2)) and complexes (1–8) were moderate to strong DNA binders, as evident from the binding constants (K(b)). The value was found to be highest for complex 2 (3.27 × 10(5) M(−1)) and lowest for 5 (6.40 × 10(3) M(−1)). A cell line study revealed that breast cancer cells were less viable to the synthesized compounds compared to that of standard drugs, cisplatin and doxorubicin, at the same concentration. The compounds were also screened for in vitro antibacterial activity for which complex 2 showed a promising broad-spectrum effect against all tested strains of bacteria, almost in the proximity of the reference drug kanamycin, while the rest of the compounds displayed activity against selected strains. The Royal Society of Chemistry 2023-04-17 /pmc/articles/PMC10107730/ /pubmed/37077261 http://dx.doi.org/10.1039/d3ra00982c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Mahmood, Khalid Akhter, Zareen Perveen, Fouzia Aisha, Bibi, Muneeba Ismail, Hammad Tabassum, Nida Yousuf, Sammer Ashraf, Ahmad Raza Qayyum, Muhammad Abdul Synthesis, DNA binding and biological evaluation of benzimidazole Schiff base ligands and their metal(ii) complexes |
title | Synthesis, DNA binding and biological evaluation of benzimidazole Schiff base ligands and their metal(ii) complexes |
title_full | Synthesis, DNA binding and biological evaluation of benzimidazole Schiff base ligands and their metal(ii) complexes |
title_fullStr | Synthesis, DNA binding and biological evaluation of benzimidazole Schiff base ligands and their metal(ii) complexes |
title_full_unstemmed | Synthesis, DNA binding and biological evaluation of benzimidazole Schiff base ligands and their metal(ii) complexes |
title_short | Synthesis, DNA binding and biological evaluation of benzimidazole Schiff base ligands and their metal(ii) complexes |
title_sort | synthesis, dna binding and biological evaluation of benzimidazole schiff base ligands and their metal(ii) complexes |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107730/ https://www.ncbi.nlm.nih.gov/pubmed/37077261 http://dx.doi.org/10.1039/d3ra00982c |
work_keys_str_mv | AT mahmoodkhalid synthesisdnabindingandbiologicalevaluationofbenzimidazoleschiffbaseligandsandtheirmetaliicomplexes AT akhterzareen synthesisdnabindingandbiologicalevaluationofbenzimidazoleschiffbaseligandsandtheirmetaliicomplexes AT perveenfouzia synthesisdnabindingandbiologicalevaluationofbenzimidazoleschiffbaseligandsandtheirmetaliicomplexes AT aisha synthesisdnabindingandbiologicalevaluationofbenzimidazoleschiffbaseligandsandtheirmetaliicomplexes AT bibimuneeba synthesisdnabindingandbiologicalevaluationofbenzimidazoleschiffbaseligandsandtheirmetaliicomplexes AT ismailhammad synthesisdnabindingandbiologicalevaluationofbenzimidazoleschiffbaseligandsandtheirmetaliicomplexes AT tabassumnida synthesisdnabindingandbiologicalevaluationofbenzimidazoleschiffbaseligandsandtheirmetaliicomplexes AT yousufsammer synthesisdnabindingandbiologicalevaluationofbenzimidazoleschiffbaseligandsandtheirmetaliicomplexes AT ashrafahmadraza synthesisdnabindingandbiologicalevaluationofbenzimidazoleschiffbaseligandsandtheirmetaliicomplexes AT qayyummuhammadabdul synthesisdnabindingandbiologicalevaluationofbenzimidazoleschiffbaseligandsandtheirmetaliicomplexes |