Phosphatase models: Synthesis, structure and catalytic activity of zinc complexes derived from a phenolic Mannich-base ligand

Sanyal, Ria; Chakraborty, Prateeti; Zangrando, Ennio; Das, Debasis

doi:10.1016/j.poly.2015.05.013

Cited by 18 publications

(4 citation statements)

References 58 publications

(62 reference statements)

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“…Andreae tal. described the synthesiso fI DA and EDDA supported on silica and functionalised with benzylc hloride (Si/PMC);b oth systems were complexed with metals of the lanthanide series (15)(16)(17)(18)(19)(20). [78] The choice of lanthanides was based on the Pearson concept [79] of "hard/soft acids/bases"; both ligands andm etals are hard.…”

Section: Catalysts Supported On Functionalised Silicamentioning

confidence: 99%

“…For example, the half‐life for the hydrolysis of dimethylphosphate is estimated to be 130 000 years [15] . Approaches that use photolytic degradation by sunlight [16] and biological pathways, [17] as well as their hydrolysis by biomimetic compounds, have been employed to solve the problem of the natural persistence of such compounds [18–30] . The use of biomimetic compounds offers a number of advantages, including the possibility to immobilise these compounds on the surface of insoluble solid matrices for easier handling and reuse [31] …”

Section: Introductionmentioning

confidence: 99%

“…[15] Approaches that use photolytic degradationb ys unlight [16] and biological pathways, [17] as well as their hydrolysis by biomimetic compounds, have been employed to solve the problem of the natural persistence of such compounds. [18][19][20][21][22][23][24][25][26][27][28][29][30] The use of biomimetic compounds offers a number of advantages, including the possibility to immobilise these compounds on the surface of insoluble solid matrices for easier handling and reuse. [31] Compared with extensivelys tudied homogeneousc atalysts that hydrolyse diverse phosphoester bonds, [28,[32][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50] far fewer heterogeneous systemst hat catalyse the cleavage of such bonds have been developed.…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances in Heterogeneous Catalytic Systems Containing Metal Ions for Phosphate Ester Hydrolysis

Gomes

Fernandes

Gahan

et al. 2020

Chemistry A European J

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Organophosphates are a class of organic compounds that are important for living organisms, forming the building blocks for DNA, RNA, and some essential cofactors. Furthermore, non‐natural organophosphates are widely used in industrial applications, including as pesticides; in laundry detergents; and, unfortunately, as chemical weapons agents. In some cases, the natural degradation of organophosphates can take thousands of years; this longevity creates problems associated with handling and the storage of waste generated by such phosphate esters, in particular. Efforts to develop new catalysts for the cleavage of phosphate esters have progressed in recent decades, mainly in the area of homogeneous catalysis. In contrast, the development of heterogeneous catalysts for the hydrolysis of organophosphates has not been as prominent. Herein, examples of heterogeneous systems are described and the importance of the development of heterogeneous catalysts applicable to organophosphate hydrolysis is highlighted, shedding light on recent advances related to different solid matrices that have been employed.

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Section: Catalysts Supported On Functionalised Silicamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Recent Advances in Heterogeneous Catalytic Systems Containing Metal Ions for Phosphate Ester Hydrolysis

Gomes

Fernandes

Gahan

et al. 2020

Chemistry A European J

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“…A few number of zinc‐based compounds are used in DNA/BSA binding and cleaving, and cytotoxicity activity. It is also interesting to note that there are not many reports where the phosphatase activity of zinc(II)‐Schiff base complexes have been studied …”

Section: Introductionmentioning

confidence: 99%

Zinc(II)‐N₂O₂ligation complex‐based DNA/protein binder and cleaver having enhanced cytotoxic and phosphatase activity

Neelakantan¹,

Balakrishnan²,

Balamurugan³

et al. 2018

Applied Organom Chemis

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The alkyne arms containing zinc(II) N2O2 ligation complexes (1) and (2) were prepared from 2,2′‐{cyclohexane‐1,2‐diylbis[nitrilo(E)methylylidene]}bis[5‐(prop‐2‐yn‐1‐yloxy)phenol] (L1) and 2,2′‐{1,2‐phenylenebis[nitrilo(E)methylylidene]}bis[5‐(prop‐2‐yn‐1‐yloxy)phenol] (L2) and characterized by analytical and various spectral techniques. The molecular geometry of 1 and 2 was optimized by Density Functional Theory (DFT) at B3LYP/6‐311G(d,p) level and compared with literature. The complexes are stable in solution, and their solution structure was assessed using NMR and ESI‐MS spectroscopy. Topological analysis of the electron density and nature of the bonding in the complexes has been determined by using Bader's AIM method. The interaction and binding modes of calf thymus DNA (CT‐DNA) with complexes (1 and 2) were investigated by using absorption and emission spectral and viscometric studies. The nuclease activity investigated through gel electrophoresis reveals that 1 and 2 exhibits a significant DNA cleavage activity via a hydrolytic pathway and is further confirmed by an experiment performed in the presence of T4 ligase. The protein binding ability of 1 and 2 with bovine serum albumin (BSA) protein evaluated show good protein binding propensity. In‐vitro cytotoxicity of the complexes has shown significant activity against human brain tumor (U87 MG) and breast carcinoma (BT20) cancer cell lines. The comet assay has been used to determine the extent of DNA fragmentation in cancer cells. The phosphatase activity investigated through kinetic measurements establishes that the zinc complexes possess significant hydrolytic efficiency and follow the order 2 > 1. The DFT calculations have also been carried out to support the proposed mechanistic pathway of catalytic activity.

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Biocatalysis, DNA–protein interactions, cytotoxicity and molecular docking of Cu(II), Ni(II), Zn(II) and V(IV) Schiff base complexes

Balakrishnan

Theetharappan

Kowsalya

et al. 2017

Applied Organom Chemis

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Four mononuclear metal complexes (Cu(II) (1), Ni(II) (2), Zn(II) (3) and V(IV) (4)) were synthesized using the Schiff base ligand 2,2′‐{cyclohexane‐1,2‐diylbis[nitrilo(1E)eth‐1‐yl‐1‐ylidine]}bis[5‐(prop‐2‐yn‐1‐yloxy)phenol] and structurally characterized by various spectral techniques. The catecholase‐mimicking activities of 1–4 were investigated and the results reveal that all the complexes have ability to oxidize 3,5‐di‐tert‐butylcatechol (3,5‐DTBC) to 3,5‐di‐tert‐butylquinone in aerobic conditions. Electrospray ionization mass spectrometry studies were performed for 1–4 in the presence of 3,5‐DTBC to determine the possible complex–substrate intermediates. X‐band electron paramagnetic resonance spectroscopy results indicate that the metal centres are involved in the catecholase activity. Ligand‐centred radical generation was further confirmed by density functional theory calculation. The phosphatase‐like activity of 1–4 was investigated using 4‐nitrophenylphosphate as a model substrate. All the complexes exhibit excellent phosphatase activity in acetonitrile medium. The interactions of 1–4 with calf thymus DNA (CT‐DNA) and bovine serum albumin (BSA) protein were investigated using absorption and fluorescence titration methods. All the complexes strongly interact with CT‐DNA and BSA protein. The complexes exhibit significant hydrolytic cleavage of supercoiled pUC19 DNA. Complexes 1–4 exhibit significant in vitro cytotoxicity against MCF7 (human breast cancer) and MIA‐PA‐CA‐2 (human pancreatic cancer) cell lines. Moreover, the molecular docking technique was employed to determine the binding affinity with DNA and protein molecules.

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Phosphatase models: Synthesis, structure and catalytic activity of zinc complexes derived from a phenolic Mannich-base ligand

Cited by 18 publications

References 58 publications

Recent Advances in Heterogeneous Catalytic Systems Containing Metal Ions for Phosphate Ester Hydrolysis

Recent Advances in Heterogeneous Catalytic Systems Containing Metal Ions for Phosphate Ester Hydrolysis

Zinc(II)‐N₂O₂ligation complex‐based DNA/protein binder and cleaver having enhanced cytotoxic and phosphatase activity

Biocatalysis, DNA–protein interactions, cytotoxicity and molecular docking of Cu(II), Ni(II), Zn(II) and V(IV) Schiff base complexes

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Phosphatase models: Synthesis, structure and catalytic activity of zinc complexes derived from a phenolic Mannich-base ligand

Cited by 18 publications

References 58 publications

Recent Advances in Heterogeneous Catalytic Systems Containing Metal Ions for Phosphate Ester Hydrolysis

Recent Advances in Heterogeneous Catalytic Systems Containing Metal Ions for Phosphate Ester Hydrolysis

Zinc(II)‐N2O2ligation complex‐based DNA/protein binder and cleaver having enhanced cytotoxic and phosphatase activity

Biocatalysis, DNA–protein interactions, cytotoxicity and molecular docking of Cu(II), Ni(II), Zn(II) and V(IV) Schiff base complexes

Contact Info

Product

Resources

About

Zinc(II)‐N₂O₂ligation complex‐based DNA/protein binder and cleaver having enhanced cytotoxic and phosphatase activity