Schiff base compounds as artificial metalloenzymes

Shahraki, Somaye

doi:10.1016/j.colsurfb.2022.112727

Cited by 27 publications

(5 citation statements)

References 145 publications

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“…Schiff bases are one of the most commonly encountered ligands in synthetic inorganic chemistry due to their ease of synthesis and flexibility in choice of donor atoms. Schiffbase complexes have been used in diverse research areas including spin crossover [1][2][3][4][5], models of enzyme systems [6][7][8] and supramolecular complexes [9,10]. Two types of tautomerism in Schiff bases have been a subject of inquiry: enol imine/keto enamine and aldimine/ketimine.…”

Section: Introductionmentioning

confidence: 99%

Formation of Ketimines from Aldimines in Schiff Base Condensation of Amino Acids and Imidazole-2-Carboxaldehydes: Tautomerization of Schiff Bases of Amino Acids Resulting in the Loss of Stereogenic Center

Brewer,

Butcher

et al. 2023

Inorganics

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The Schiff base reaction of imidazole-2-carboxaldehydes with the anion of alanine, leucine and phenylalanine in the presence of nickel(II) ion gives the neutral NiL2 complexes. The Schiff base ligand, L, binds through an imidazole nitrogen, NIm, the amino acid nitrogen, NAA, and a carboxylate oxygen, O, atom. The two N2O ligands bind to the nickel(II) in a meridional fashion with the NIm and O of each ligand in trans positions. These ligands can exist as the anticipated aldimine, Im − CH = NAA − CH(R) − CO2−, or the ketimine, Im − CH2NAA = C(R) − CO2−, tautomer. Tautomerization of the initially formed aldimine Schiff base results in movement of the hydrogen atom of the alpha carbon of the amino acid to the aldehyde carbon, CAld, atom of the imidazole carboxaldehyde with resultant relocation of the imine double bond in the reverse direction. Ten structures of the structurally unprecedented ketimine tautomer, prepared from imidazole-2-carboxaldehydes and a pyrazole-3-carboxaldehyde, were presented. The structural data supported the formation of the ketimines in each case, while the aldimine tautomer was observed with imidazole-4-carboxaldehydes. A rationale of this can be explained on the basis of charge distribution in the likely intermediate in the tautomerization.

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Section: Introductionmentioning

confidence: 99%

Formation of Ketimines from Aldimines in Schiff Base Condensation of Amino Acids and Imidazole-2-Carboxaldehydes: Tautomerization of Schiff Bases of Amino Acids Resulting in the Loss of Stereogenic Center

Brewer,

Butcher

et al. 2023

Inorganics

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“…Due to its special properties, including its redox potential, Mn complexes have been considered by researchers, especially in design of artificial enzyme. [ 42 ] Before using them in medical cases, their interaction with biological molecules seems necessary. Here, a Mn complex containing 1,10‐phenanthroline and thiourea was selected, and its antioxidant activity was investigated by DPPH•.…”

Section: Discussionmentioning

confidence: 99%

Improving enzymatic performance of antioxidant enzyme catalase in combination with [Mn (phen)₂Cl.H₂O]Cl.tu complex

Shahraki

Shiri

Razmara

2023

Applied Organom Chemis

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Efforts to synthesize metal complexes that have good biological potency, such as anti-cancer or antioxidant properties, have expanded. In this study, an Mn complex containing 1,10-phenanthroline (phen) and thiourea (tu), [Mn (phen) 2 Cl.H 2 O]Cl.tu, was selected, and its interaction with the antioxidant enzyme bovine liver catalase (BLC) was evaluated by spectroscopic and molecular docking methods. Our results showed that Mn complex interacts with BLC via a dynamic, endothermic, entropy-driven mechanism. The binding constants (K b ) of BLC-Mn complex were 0.62 ± 0.01, 0.73 ± 0.03, and 2.62 ± 0.09 Â 10 3 M À1 at 303, 310, and 317 K, respectively. During complex interaction with catalase, the most important forces involved were hydrophobic forces. Considering that the quenching rate of tryptophan (Trp) was higher than that of tyrosine (Tyr), it can be concluded that Trp is closer to the Mn complex interaction site than Tyr. The CD spectra showed that the BLC secondary structure became more stable in the presence of the Mn complex and could be a reason for improving the catalytic activity of this enzyme. Molecular docking was used to predict that the Mn complex is able to bind to BLC and to identify specific residues. In general, the above Mn complex can be further evaluated as a suitable synthetic metallodrug due to its good antioxidant activity and binding function that improves the enzymatic activity of catalase.

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“…Many complexes are known to play vital roles in biological systems; e.g., metalloenzymes. [46][47][48] With its serendipitous discovery by Rosenberg and its anti-cancer activity, cisplatin is considered one of the best anti-cancer drugs on the market to date. Moreover, Platinum(II)-based compounds are known for their ability to induce nucleic acid crosslinks and adducts that can efficiently inhibit the transcription and replication processes in cancer cells.…”

Section: Complexes With Significance Towards Chemical Synthesismentioning

confidence: 99%

Click-derived multifunctional metal complexes for diverse applications

Ahmad

Chanda

2023

Chem. Soc. Rev.

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Schiff base compounds as artificial metalloenzymes

Cited by 27 publications

References 145 publications

Formation of Ketimines from Aldimines in Schiff Base Condensation of Amino Acids and Imidazole-2-Carboxaldehydes: Tautomerization of Schiff Bases of Amino Acids Resulting in the Loss of Stereogenic Center

Formation of Ketimines from Aldimines in Schiff Base Condensation of Amino Acids and Imidazole-2-Carboxaldehydes: Tautomerization of Schiff Bases of Amino Acids Resulting in the Loss of Stereogenic Center

Improving enzymatic performance of antioxidant enzyme catalase in combination with [Mn (phen)₂Cl.H₂O]Cl.tu complex

Click-derived multifunctional metal complexes for diverse applications

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Schiff base compounds as artificial metalloenzymes

Cited by 27 publications

References 145 publications

Formation of Ketimines from Aldimines in Schiff Base Condensation of Amino Acids and Imidazole-2-Carboxaldehydes: Tautomerization of Schiff Bases of Amino Acids Resulting in the Loss of Stereogenic Center

Formation of Ketimines from Aldimines in Schiff Base Condensation of Amino Acids and Imidazole-2-Carboxaldehydes: Tautomerization of Schiff Bases of Amino Acids Resulting in the Loss of Stereogenic Center

Improving enzymatic performance of antioxidant enzyme catalase in combination with [Mn (phen)2Cl.H2O]Cl.tu complex

Click-derived multifunctional metal complexes for diverse applications

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Product

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Improving enzymatic performance of antioxidant enzyme catalase in combination with [Mn (phen)₂Cl.H₂O]Cl.tu complex