Designing of novel zinc(<scp>ii</scp>) Schiff base complexes having acyl hydrazone linkage: study of phosphatase and anti-cancer activities

Dasgupta, Sanchari; Karim, Suhana; Banerjee, Saswati; Saha, Moumita; Saha, Krishna Das; Das, Debasis

doi:10.1039/c9dt04636d

Cited by 80 publications

(26 citation statements)

References 44 publications

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“…The efficiency of PTIH in HepG2 cells was also substantially good compared to previous studies on some hydrazone metal complexes (15,29). PTIH showed good cytotoxic activity in the A549 cell when compared to the effects of some similar hydrazone metal complexes in A549 cells (30,31). In HUH7 cells, PTIH also showed good anticancer activity compared to some similar molecules in the literature (32,33).…”

Section: Discussionsupporting

confidence: 47%

Antitumoral Properties of a Pincer-Type Isonicotinohydrazone-Hg(II) Complex

Demir¹,

Sezan²,

Derinöz³

et al. 2021

ejb

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Objective:The aim of this study was to evaluate the antitumoral properties of the novel Hg(SCN) 2 complex of a pincer-type isonicotinohyrazone ligand (PTIH). Materials and Methods:Hydrazine ligands were prepared through a Schiff base condensation between the 2-Acetylpyridine and isonicotinoyl acid hydrazide. PTIH was synthetized by a branch tube method using Hg(SCN) 2 . In vitro cell killing activity, the induction of apoptosis, the influence on motility, and the effects on mRNA expression to a motility-related gene (E-cadherin) of PTIH were evaluated in A549, HepG2, HUH7 cancer cell lines, and BEAS2B non-cancer cell line.Results: PTIH was found to be cytotoxic to cancer cells, compared to non-cancers, and induced apoptosis. Additionally, it suppressed cell migration in A549 cells, leading to an increase in the levels of E-cadherin mRNA expression, and decreased colony formation in HepG2 and HUH7 cells. Through UV titration studies, it was determined that PTIH showed albumin binding and interacted with DNA by electrostatically and/or groove binding. Conclusion:PTIH exerted more cytotoxic effects in some cancer cells than in normal cells. This feature and other anticancer properties make it a promising agent.

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Section: Discussionsupporting

confidence: 47%

Antitumoral Properties of a Pincer-Type Isonicotinohydrazone-Hg(II) Complex

Demir¹,

Sezan²,

Derinöz³

et al. 2021

ejb

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“…The FT‐IR spectra of all these materials contain sharp band at ~1628 cm −1 which is the signature of C═N vibration of Schiff base moiety and the band ~1444 cm −1 is observed due to benzene skeletal vibration. [ 63 ] Therefore, the complexes retained their identity after nanofabrication.…”

Section: Resultsmentioning

confidence: 99%

A mechanistic approach for in‐vitro anticancer activity via nucleic acid fragmentation by copper(II) complex anchored on MCM‐41

Karim

Dasgupta

Parveen

et al. 2022

Applied Organom Chemis

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Three new mononuclear copper Schiff base complexes, namely, ([Cu(L1)Cl].CH3CN (HmC_1), [Cu(L2)Cl].CH3CN (HmC_2) and [Cu(L3)Cl].CH3CN (HmC_3) derived from ONO donor tridentate ligands HL1, HL2 and HL3, respectively, have been synthesized to check their efficacy as target‐specific next‐generation anticancer therapeutics. All the HmCs have been characterized by using various physicochemical techniques (i.e., single‐crystal X‐ray analysis, Fourier transform infrared [FT‐IR] spectroscopy and elemental analysis). Among the synthesized Schiff base complexes, HmC_3 was turned out to be most effective in killing cancer cell carried out on cultured human breast cancer cell line (MDA‐MB‐231) and human lung carcinoma cell line (A549). Finally, in order to improve the cellular permeability, particle size of HmC_3 was scaling down to nano‐regime by immobilizing it onto a suitable matrix MCM‐41@APTES (MCM‐41 = Mobil Composition of Matter No. 41 and APTES = 3‐aminopropyltriethoxysilane) to generate MCM‐41@APTES@HmC_3 (MCM‐41@APTES@HmC_3 = HtC_3). Field‐emission scanning electron microscope (FESEM) and dynamic light scattering (DLS) study revealed the particle size of the synthesized HtC_3 nano‐composite was within nano‐regime and therefore could be further effective for biomedical applications. Furthermore, HtC_3 displayed better cancer cell killing property. To get insight into the mechanism of action of HtC_3, Annexin V‐FITC/PI analysis and TUNEL assay revealed that DNA damage phenomenon is accompanied with changes in cellular morphology leading to cell apoptosis. Cell migration assay on MDA‐MB‐231 cell with HtC_3 exposed the effectiveness of HtC_3 in arresting cancer cell migration. Therefore, all the in‐vitro studies demonstrated that the immobilization of the copper Schiff base complex onto a suitable matrix increased its efficiency and becomes a promising anticancer nano‐therapeutic agent.

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“…Phosphatase is an assemblage of hydrolytic enzymes that catalyze the dephosphorylation reaction, that is, hydrolysis of phosphate monoesteric, diesteric, and triesteric P–O bonds − This is one of the essential biological reactions, as this is involved in cellular signaling, synthesis of proteins, replication of genetic material to energy, and so forth. , The uncatalyzed hydrolysis is extremely slow and the cleavage of P–O bonds is accelerated in the presence of bivalent metal ions. − Over the last few decades, many groups including our group have been involved in designing the bio-mimicking models to establish plausible mechanistic pathways of phosphatase activity. − Generally, dinuclear complexes are more efficient than their mononuclear counterparts because two metal centers may act mutually in substrate binding to catalyst, activation of the nucleophile, and cleavage of the bond. − The availability of a nucleophile (water or hydroxo) in the close vicinity of the metal center(s) is the predominant factor of phosphatase activity and attack of nucleophile on the phosphorus center is the rate-determining step of hydrolysis . The other factors that dictate the rate of hydrolysis are reaction conditions, Lewis acidity of metal centers, stereochemistry, presence of oxo-anions, the coordination domain of metal ions, and the presence of electronegative atoms in the ligand backbone. − In recent times, designing of bio-mimicking models with additional biological applications always draws special attention of the bio-inorganic chemists . The incorporation of metals to the ligand system enhanced the biological activity of the overall entity.…”

Section: Introductionmentioning

confidence: 99%

Executing a Series of Zinc(II) Complexes of Homologous Schiff Base Ligands for a Comparative Analysis on Hydrolytic, Antioxidant, and Antibacterial Activities

Chowdhury

Dasgupta

Khatua

et al. 2020

ACS Appl. Bio Mater.

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Six zinc(II) complexes, namely, [Zn(HL 1 H)Cl 2 ] (1), [Zn(HL 1 H)Br 2 ] (2), [Zn 2 (HL 1 H) 2 (OH)I 2 ]•I (3), [Zn(HL 2 )-Cl] (4), [Zn 2 (HL 2 )Br 3 ] (5), and [Zn(HL 2 )I] (6) have been manufactured by using two homologous Schiff base ligands H 2 L 1 and H 2 L 2 for the purpose of perlustrating their phosphatase-like activity, antioxidant activity, and antibacterial activity. Complexes 1, 2, 4, and 5 have been reported earlier by us, whereas complexes 3 and 6 have been synthesized and structurally characterized by regular physicochemical methods The hydrolytic property of the six complexes has been evaluated by checking the hydrolysis of the P−O bond of a widely used substrate, namely, disodium salt of (para-nitrophenyl)phosphate (PNPP) in 97.5% (v/v) mixture of N,N-dimethylformamide and water (DMF−water). Complexes 2− 5 have profound efficiency toward hydrolysis of phosphate ester bonds, and complexes 1 and 6 were noted to be inactive toward hydrolysis. Complex 3 displayed the highest efficacy among the six complexes. Additionally, antioxidant and antibacterial activities of the complexes were studied thoroughly. A detailed study of their antioxidant property revealed that complex 3 manifested superior radical scavenging activity, thus exhibiting the highest antioxidant property. The antibacterial activity was tested using four investigating bacteria, specifically Listeria monocytogenes ATCC19111, Staphylococcus aureus ATCC 700699, Salmonella typhimurium ATCC 23564, and Escherichia coli ATCC 25922 by determining minimum inhibitory concentration (MIC) values using the microdilution method. Here as well, complex 3 exhibited the highest activity to both Gram positive and Gram negative bacteria. The chemistry behind these experimental findings has been manifested by shedding light upon the structural features of the complexes. The suitable choice of ligand H 2 L 1 where one methylene group is less than its homologous ligand and metal precursor (ZnI 2 ) imparts a unique hydroxo-bridged molecular geometry and 2D hydrogen bonding network which in turn probably enhances the hydrolytic and biological activities of complex 3.

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Designing of novel zinc(ii) Schiff base complexes having acyl hydrazone linkage: study of phosphatase and anti-cancer activities

Abstract: The phosphatase and anti-cancer activities of three novel acyl hydrazone based zinc(ii) Schiff base complexes have been unveiled.

Cited by 80 publications

References 44 publications

Antitumoral Properties of a Pincer-Type Isonicotinohydrazone-Hg(II) Complex

Antitumoral Properties of a Pincer-Type Isonicotinohydrazone-Hg(II) Complex

A mechanistic approach for in‐vitro anticancer activity via nucleic acid fragmentation by copper(II) complex anchored on MCM‐41

Executing a Series of Zinc(II) Complexes of Homologous Schiff Base Ligands for a Comparative Analysis on Hydrolytic, Antioxidant, and Antibacterial Activities

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