Synthesis, structure, anticancer, and antioxidant activity of para-xylyl linked bis-benzimidazolium salts and respective dinuclear Ag(I) N-heterocyclic carbene complexes (Part-II)

Haque, Rosenani A.; Iqbal, Muhammad Adnan; Asekunowo, Patrick O.; Majid, Amin Malik Shah Abdul; Ahamed, Mohamed B. Khadeer; Umar, Muhammad Ihtisham; Al-Rawi, Sawsan S.; Al‐Suede, Fouad Saleih R.

doi:10.1007/s00044-012-0461-8

Cited by 66 publications

(26 citation statements)

References 19 publications

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“…This will further facilitate the permeation of the complexes into the lipid layers which leads to blocking of the metal binding sites in the enzymes of microorganisms. The present result is in accord with our previous reports [38] where we mentioned that halide salts of compounds are more active than compounds with hexafluorophosphate as counter anions. These Ag-NHC complexes (2)(3)(4) bearing an electron-withdrawing nitrile functionality at N-position have superior stability over AgNO 3 in the bacterial solution since the growth of bacteria treated with these complexes on a daily basis were delayed for a longer time.…”

Section: Antibacterial Activitysupporting

confidence: 96%

Counterion-induced modulation in biochemical properties of nitrile functionalized silver(I)-N-heterocyclic carbene complexes

Asekunowo

Haque

2014

Journal of Coordination Chemistry

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The new Ag(I) complexes (2-4) with proligand 1 were prepared and characterized as prospective antibacterial drug candidates. These compounds consist of a Ag(I) center linearly coordinated to two identical N-heterocyclic carbenes (NHCs). Crystal structures were solved for complexes 3 and 4, the resulting structural data being in good agreement with expectations. We wondered whether the presence of different counter ions in these compounds might lead to modulation of their biological properties. Notably, in spite of their similar structural pattern, Ag(I)-NHC complex 2 with Br − manifested better antibacterial actions than complexes 3 and 4 with PF À 6 and BF À 4 , respectively. Stability study over time in bacterial solutions revealed that these complexes have better stability than AgNO 3 . Their interaction with DNA and RNA was explored, cleavage activity indicates that all Ag(I)-NHC complexes exhibited interesting nuclease activity via non-oxidative pathway.

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Section: Antibacterial Activitysupporting

confidence: 96%

Counterion-induced modulation in biochemical properties of nitrile functionalized silver(I)-N-heterocyclic carbene complexes

Asekunowo

Haque

2014

Journal of Coordination Chemistry

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“…Anti-microbial properties of Ag(I)-NHC complexes have been the subject of investigation. [21][22][23] Inspired by our previous research on the anti-cancer potential of benzimidazole-based binuclear Ag (I)-NHC complexes [24,25] and due to the fact that several studies have demonstrated the promising biological applications of binuclear complexes of both functionalized and non-functionalized NHCs as potent anti-cancer/anti-microbial agents against a variety of pathogens. [26] the current work is an effort to further explore this area of research.…”

Section: Introductionmentioning

confidence: 99%

Benzimidazole‐based silver(I)–N‐heterocyclic carbene complexes as anti‐bacterials: synthesis, crystal structures and nucleic acids interaction studies

Asekunowo

Haque

Razali

et al. 2014

Applied Organom Chemis

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A series of new benzimidazolium salts as N-heterocyclic carbene (NHC) precursors has been synthesized. Reactions of these salts with Ag 2 O with varying metal-to-salt ratio facilitate the formation of a series of new binuclear and mononuclear Ag(I)-NHC complexes. All compounds were characterized using physicochemical and spectroscopic techniques. Single-crystal X-ray diffraction study reveals a binuclear structure for one of the complexes and a mononuclear one for two others. These complexes exist as cationic Ag(I)-NHC complexes with the chelation of carbene carbons to the silver centre in an almost linear manner. The compounds were screened for their anti-bacterial activities against Staphylococcus aureus (ATCC 12600) as a Gram-positive bacterium and Escherichia coli (ATCC 25922) as a Gram-negative bacterium. The results show that both bacteria appear markedly inhibited. Furthermore, the results suggest the possibility of steric variation as a modulation of the anti-bacterial activities. The nuclease activities of the compounds were assessed using gel electrophoresis and the results indicate that these complexes can cleave or degrade DNA and RNA via a non-oxidative mechanism.

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“…Human colorectal cancer/tumor (HCT) is the third most common type of cancer in older males and the fourth most common cause of cancer deaths worldwide. According to an estimate, every year more than 945,000 people develop this cancer and around 492,000 patients die (Haque et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural elucidation of two new series of aurone derivatives as potent inhibitors against the proliferation of human cancer cells

et al. 2015

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Two new series of aurone compounds were synthesized via an oxidative cyclization reaction of 2 0 -hydroxy-chalcones. Series (A) consists of 1a-3a aurones with different substitutions on a B-ring at position 4 0 , and series (B) is made up of 1b-3b aurones that have different substitutions at position 2 0 of a B-ring. Structures of the synthesized compounds were characterized and confirmed by FTIR (1D and 2D NMR) and EI mass spectral studies. The molecular structure of 2b was further confirmed by the X-ray crystallographic technique, with the compound found to be in Z-isomeric form. The compounds of both series were tested for their antiproliferative activity against human colorectal tumor (HCT 116), human chronic myelogenous leukemia (K562) and hormone-dependent breast cancer (MCF-7) cell lines according to an MTT assay. Series (B) exhibited a higher cytotoxic effect on the cancer cell lines compared to series (A). Selectively, the most promising results have been shown by the two most active compounds, 1b (Z-5,7, 2 0 -trichloro-aurone), which resulted in IC 50 values of 36, 23 and 23 lM against HCT 116, MCF-7 and K562 cancer cells, respectively. Compound 3a (Z-5, 7-dichloro-4 0 -methyl-aurone) exhibited the highest activity against the K562 cell line (IC 50 = 20 lM), which can be compared to that of the standard drug, betulinic acid, with an IC 50 value of 15 lM. The results of the present study suggested that aurone derivatives emerged as a potential candidate for the development of future chemotherapeutic agents.

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Synthesis, structure, anticancer, and antioxidant activity of para-xylyl linked bis-benzimidazolium salts and respective dinuclear Ag(I) N-heterocyclic carbene complexes (Part-II)

Cited by 66 publications

References 19 publications

Counterion-induced modulation in biochemical properties of nitrile functionalized silver(I)-N-heterocyclic carbene complexes

Counterion-induced modulation in biochemical properties of nitrile functionalized silver(I)-N-heterocyclic carbene complexes

Benzimidazole‐based silver(I)–N‐heterocyclic carbene complexes as anti‐bacterials: synthesis, crystal structures and nucleic acids interaction studies

Synthesis and structural elucidation of two new series of aurone derivatives as potent inhibitors against the proliferation of human cancer cells

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