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Design and synthesis of novel complexes containing N-phenyl-1H-pyrazole moiety: Ni complex as potential antifungal and antiproliferative compound.

Abstract

Cu(II) (1), Ni(II) (2), Cr(III) (3) and Fe(III) (4) complexes with 3-acetyl-4-benzoyl-1-phenyl-1H-pyrazole (L1) were prepared and structurally characterized. Usual coordination of L1 was achieved through nitrogen of pyrazole moiety and carbonyl acetyl group. Electronic spectra of the complexes indicate that the geometry of the metal center was six coordinate octahedral. In vitro antimicrobial activity of the ligand and complex compounds was screened in terms of antibacterial effect on Staphylococcus aureus (Gram-positive), Escherichia coli (Gram-negative) and antifungal effect on the fungi Aspergillus flavus and candida albicans using the modified Kirby-Bauer disc diffusion and minimum inhibitory concentrations (MIC) methods. Ni(II) complex (2) exhibited remarkable antifungal inhibition against Candida albicans equal to the standard antifungal agent. To continue our study some structural modifications are formed by adding 4-fluoro-benzoyl moiety to L1 in different forms to produce different ligands, 3-acetyl-4-(4-flourobenzoyl)-1-phenyl-1H-pyrazole (L2) and 3-[(3-acetyl-1-phenyl-1H-4-pyrazolyl)carbonyl]-1-phenyl-4-(4-flourobenzoyl)-1H-pyrazole (L3), Ni complexes (5 and 6) are prepared and comparable in vitro antimicrobial study is evaluated. In vitro cytotoxicity of the Ni(II) complex (2) is studied using MTT assay. The analysis of the cell test showed that (2) displayed quite small cytotoxic response at the higher concentration level which indeed would further enable us for more opportunities in therapeutic and biomedical challenges. Both of the capability as a potent in vitro antifungal agent and the cell test analysis show Ni(II) complex (2) as a promising material in the translation of observed in vitro biological phenomenon into clinical therapies settings.

Authors+Show Affiliations

Chemistry Department, Faculty of Science, Cairo University, 12613 Giza, Egypt. nadinealy@hotmail.comNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

23871973

Citation

El-Gamel, Nadia E A., and Thoraya A. Farghaly. "Design and Synthesis of Novel Complexes Containing N-phenyl-1H-pyrazole Moiety: Ni Complex as Potential Antifungal and Antiproliferative Compound." Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, vol. 115, 2013, pp. 469-75.
El-Gamel NE, Farghaly TA. Design and synthesis of novel complexes containing N-phenyl-1H-pyrazole moiety: Ni complex as potential antifungal and antiproliferative compound. Spectrochim Acta A Mol Biomol Spectrosc. 2013;115:469-75.
El-Gamel, N. E., & Farghaly, T. A. (2013). Design and synthesis of novel complexes containing N-phenyl-1H-pyrazole moiety: Ni complex as potential antifungal and antiproliferative compound. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 115, 469-75. https://doi.org/10.1016/j.saa.2013.06.067
El-Gamel NE, Farghaly TA. Design and Synthesis of Novel Complexes Containing N-phenyl-1H-pyrazole Moiety: Ni Complex as Potential Antifungal and Antiproliferative Compound. Spectrochim Acta A Mol Biomol Spectrosc. 2013;115:469-75. PubMed PMID: 23871973.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Design and synthesis of novel complexes containing N-phenyl-1H-pyrazole moiety: Ni complex as potential antifungal and antiproliferative compound. AU - El-Gamel,Nadia E A, AU - Farghaly,Thoraya A, Y1 - 2013/06/29/ PY - 2012/12/31/received PY - 2013/06/07/revised PY - 2013/06/19/accepted PY - 2013/7/23/entrez PY - 2013/7/23/pubmed PY - 2014/3/22/medline KW - Antifungal activity KW - Candida albicans KW - Pyrazole derivatives KW - Spectroscopic characterization KW - Thermal studies SP - 469 EP - 75 JF - Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy JO - Spectrochim Acta A Mol Biomol Spectrosc VL - 115 N2 - Cu(II) (1), Ni(II) (2), Cr(III) (3) and Fe(III) (4) complexes with 3-acetyl-4-benzoyl-1-phenyl-1H-pyrazole (L1) were prepared and structurally characterized. Usual coordination of L1 was achieved through nitrogen of pyrazole moiety and carbonyl acetyl group. Electronic spectra of the complexes indicate that the geometry of the metal center was six coordinate octahedral. In vitro antimicrobial activity of the ligand and complex compounds was screened in terms of antibacterial effect on Staphylococcus aureus (Gram-positive), Escherichia coli (Gram-negative) and antifungal effect on the fungi Aspergillus flavus and candida albicans using the modified Kirby-Bauer disc diffusion and minimum inhibitory concentrations (MIC) methods. Ni(II) complex (2) exhibited remarkable antifungal inhibition against Candida albicans equal to the standard antifungal agent. To continue our study some structural modifications are formed by adding 4-fluoro-benzoyl moiety to L1 in different forms to produce different ligands, 3-acetyl-4-(4-flourobenzoyl)-1-phenyl-1H-pyrazole (L2) and 3-[(3-acetyl-1-phenyl-1H-4-pyrazolyl)carbonyl]-1-phenyl-4-(4-flourobenzoyl)-1H-pyrazole (L3), Ni complexes (5 and 6) are prepared and comparable in vitro antimicrobial study is evaluated. In vitro cytotoxicity of the Ni(II) complex (2) is studied using MTT assay. The analysis of the cell test showed that (2) displayed quite small cytotoxic response at the higher concentration level which indeed would further enable us for more opportunities in therapeutic and biomedical challenges. Both of the capability as a potent in vitro antifungal agent and the cell test analysis show Ni(II) complex (2) as a promising material in the translation of observed in vitro biological phenomenon into clinical therapies settings. SN - 1873-3557 UR - https://www.unboundmedicine.com/medline/citation/23871973/Design_and_synthesis_of_novel_complexes_containing_N_phenyl_1H_pyrazole_moiety:_Ni_complex_as_potential_antifungal_and_antiproliferative_compound_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S1386-1425(13)00671-9 DB - PRIME DP - Unbound Medicine ER -