Synthesis, Characterization, In Silico And In Vitro Evaluations Of Benzimidazolium Derived N-heterocyclic Carbenes And Their Silver (I)-nhc Complexes

Two new series of asymmetrical benzimidazolium-based N-heterocyclic carbene (NHC) ligands and their Ag(I)-NHC complexes were synthesised and characterised using Fourier-transform infrared (FTIR) and Fourier-transform nuclear magnetic resonance (FT-NMR) spectroscopies and CHN elemental analysis. The...

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Main Author:	Zin, Nor Farah Hani Md
Format:	Thesis
Language:	English
Published:	2023
Subjects:	QD1-999 Chemistry
Online Access:	http://eprints.usm.my/60663/1/NOR%20FARAH%20HANI%20BINTI%20MD%20ZIN%20-%20TESIS24.pdf
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id	my-usm-ep.60663
record_format	uketd_dc
spelling	my-usm-ep.606632024-05-23T03:24:57Z Synthesis, Characterization, In Silico And In Vitro Evaluations Of Benzimidazolium Derived N-heterocyclic Carbenes And Their Silver (I)-nhc Complexes 2023-09 Zin, Nor Farah Hani Md QD1-999 Chemistry Two new series of asymmetrical benzimidazolium-based N-heterocyclic carbene (NHC) ligands and their Ag(I)-NHC complexes were synthesised and characterised using Fourier-transform infrared (FTIR) and Fourier-transform nuclear magnetic resonance (FT-NMR) spectroscopies and CHN elemental analysis. The ligands, 1-13 were synthesized via alkylation of 1-methyl/octadecylbenzimidazole with alkyl bromides (C = 4-18 in even parity), These ligands were reacted with silver oxide (Ag2O) via in situ deprotonation reaction, followed by metathesis reaction with potassium hexafluorophosphate (KPF6) to yield Ag(I)-NHC complexes, 14-25. The binding free energies (ΔG), inhibition constants (Ki) and the interactions of ligands 1-13 and selenoenzyme thioredoxin reductase (TrxR) were predicted using molecular docking. The in vitro cytotoxicity of all compounds, 1-25 against human cervical cancer cells (HeLa) and human skin fibroblasts (Hs27) were evaluated using the MTT assay. The length of alkyl chains on nitrogen atoms in the benzimidazolium moiety, as well as the presence of Ag+ ions, influenced the cytotoxicity of these compounds. Cytotoxicity of these compounds increased with increasing alkyl chain length. For ligands, the long-chain homologues, 9-11 (C10-C14) were more potent (IC50 = 1.35-12.68 μM) and selective than the short-chain analogues, 1-4 (IC50 = 3.53-35 μM) against HeLa cells. 2023-09 Thesis http://eprints.usm.my/60663/ http://eprints.usm.my/60663/1/NOR%20FARAH%20HANI%20BINTI%20MD%20ZIN%20-%20TESIS24.pdf application/pdf en public masters Universiti Sains Malaysia Pusat Pengajian Sains Kimia
institution	Universiti Sains Malaysia
collection	USM Institutional Repository
language	English
topic	QD1-999 Chemistry
spellingShingle	QD1-999 Chemistry Zin, Nor Farah Hani Md Synthesis, Characterization, In Silico And In Vitro Evaluations Of Benzimidazolium Derived N-heterocyclic Carbenes And Their Silver (I)-nhc Complexes
description	Two new series of asymmetrical benzimidazolium-based N-heterocyclic carbene (NHC) ligands and their Ag(I)-NHC complexes were synthesised and characterised using Fourier-transform infrared (FTIR) and Fourier-transform nuclear magnetic resonance (FT-NMR) spectroscopies and CHN elemental analysis. The ligands, 1-13 were synthesized via alkylation of 1-methyl/octadecylbenzimidazole with alkyl bromides (C = 4-18 in even parity), These ligands were reacted with silver oxide (Ag2O) via in situ deprotonation reaction, followed by metathesis reaction with potassium hexafluorophosphate (KPF6) to yield Ag(I)-NHC complexes, 14-25. The binding free energies (ΔG), inhibition constants (Ki) and the interactions of ligands 1-13 and selenoenzyme thioredoxin reductase (TrxR) were predicted using molecular docking. The in vitro cytotoxicity of all compounds, 1-25 against human cervical cancer cells (HeLa) and human skin fibroblasts (Hs27) were evaluated using the MTT assay. The length of alkyl chains on nitrogen atoms in the benzimidazolium moiety, as well as the presence of Ag+ ions, influenced the cytotoxicity of these compounds. Cytotoxicity of these compounds increased with increasing alkyl chain length. For ligands, the long-chain homologues, 9-11 (C10-C14) were more potent (IC50 = 1.35-12.68 μM) and selective than the short-chain analogues, 1-4 (IC50 = 3.53-35 μM) against HeLa cells.
format	Thesis
qualification_level	Master's degree
author	Zin, Nor Farah Hani Md
author_facet	Zin, Nor Farah Hani Md
author_sort	Zin, Nor Farah Hani Md
title	Synthesis, Characterization, In Silico And In Vitro Evaluations Of Benzimidazolium Derived N-heterocyclic Carbenes And Their Silver (I)-nhc Complexes
title_short	Synthesis, Characterization, In Silico And In Vitro Evaluations Of Benzimidazolium Derived N-heterocyclic Carbenes And Their Silver (I)-nhc Complexes
title_full	Synthesis, Characterization, In Silico And In Vitro Evaluations Of Benzimidazolium Derived N-heterocyclic Carbenes And Their Silver (I)-nhc Complexes
title_fullStr	Synthesis, Characterization, In Silico And In Vitro Evaluations Of Benzimidazolium Derived N-heterocyclic Carbenes And Their Silver (I)-nhc Complexes
title_full_unstemmed	Synthesis, Characterization, In Silico And In Vitro Evaluations Of Benzimidazolium Derived N-heterocyclic Carbenes And Their Silver (I)-nhc Complexes
title_sort	synthesis, characterization, in silico and in vitro evaluations of benzimidazolium derived n-heterocyclic carbenes and their silver (i)-nhc complexes
granting_institution	Universiti Sains Malaysia
granting_department	Pusat Pengajian Sains Kimia
publishDate	2023
url	http://eprints.usm.my/60663/1/NOR%20FARAH%20HANI%20BINTI%20MD%20ZIN%20-%20TESIS24.pdf
_version_	1804888980923088896

Synthesis, Characterization, In Silico And In Vitro Evaluations Of Benzimidazolium Derived N-heterocyclic Carbenes And Their Silver (I)-nhc Complexes

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