Inactivation of bovine plasma amine oxidase by 1,1,1–trihalo–3–aminopropanes

Kim, Jisook; Lee, Irene N.

doi:10.1016/j.bioorg.2017.10.007

Cited by 3 publications

(1 citation statement)

References 35 publications

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“…Because the PAs proved to act as BSAO substrates, they would undergo a covalent interaction with the TPQ, making a Schiff intermediate before the oxygen activation and the subsequent oxidation of the imine (Supporting Information, Figure S5). ,, This mechanism was observed for the imidazole and 2-hydrazinopyridine bound to TPQ in the human semicarbazide-sensitive amine oxidase (SSAO, PDB entry code 2Y74) and in the vascular adhesion protein-1 (VAP1, PDB entry code 2C11). Following the PA oxidation mechanism (Supporting Information, Figure S5), a CMDock protocol was set up to investigate the possible mechanism of interaction between BSAO and the titled PAs (Figure ).…”

Section: Resultsmentioning

confidence: 98%

Bovine Serum Amine Oxidase and Polyamine Analogues: Chemical Synthesis and Biological Evaluation Integrated with Molecular Docking and 3-D QSAR Studies

Ragno

Minarini

Proia

et al. 2022

J. Chem. Inf. Model.

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Natural polyamines (PAs) are key players in cellular homeostasis by regulating cell growth and proliferation. Several observations highlight that PAs are also implicated in pathways regulating cell death. Indeed, the PA accumulation cytotoxic effect, maximized with the use of bovine serum amine oxidase (BSAO) enzyme, represents a valuable strategy against tumor progression. In the present study, along with the design, synthesis, and biological evaluation of a series of new spermine (Spm) analogues (1–23), a mixed structure-based (SB) and ligand-based (LB) protocol was applied. Binding modes of BSAO-PA modeled complexes led to clarify electrostatic and steric features likely affecting the BSAO-PA biochemical kinetics. LB and SB three-dimensional quantitative structure–activity relationship (Py-CoMFA and Py-ComBinE) models were developed by means of the 3d-qsar.com portal, and their analysis represents a strong basis for future design and synthesis of PA BSAO substrates for potential application in oxidative stress-induced chemotherapy.

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Section: Resultsmentioning

confidence: 98%

Bovine Serum Amine Oxidase and Polyamine Analogues: Chemical Synthesis and Biological Evaluation Integrated with Molecular Docking and 3-D QSAR Studies

Ragno

Minarini

Proia

et al. 2022

J. Chem. Inf. Model.

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Studies on lysozyme modifications induced by substituted p-benzoquinones

Kim

Thomas

Ewald

et al. 2019

Bioorganic Chemistry

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Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis

et al. 2018

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The first enantioselective formal [3 + 2] cycloaddition between α-isocyanoesters and trifluoromethylketones to give 5trifluoromethyl-2-oxazolines bearing two contiguous stereogenic centers, one of them being a quaternary stereocenter substituted with a CF 3 group, has been developed. The reaction is based upon a multicatalytic approach that combines a bifunctional Brønsted basesquaramide organocatalyst and Ag + as Lewis acid. The reaction could be achieved with a range of aryl and heteroaryl trifluoromethyl ketones, and the resulting oxazolines were obtained with good to excellent diastereo-and enantioselectivity. Recently, on the basis of a cooperative strategy previously reported by Escolano et al. for the asymmetric cycloaddition of isocyanoacetates with vinyl ketones, 14 our group developed a highly catalytic enantioselective cycloaddition reaction between ketones and α-isocyanoesters using a multicatalytic approach that combined a bifunctional Brønsted base

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Inactivation of bovine plasma amine oxidase by 1,1,1–trihalo–3–aminopropanes

Cited by 3 publications

References 35 publications

Bovine Serum Amine Oxidase and Polyamine Analogues: Chemical Synthesis and Biological Evaluation Integrated with Molecular Docking and 3-D QSAR Studies

Bovine Serum Amine Oxidase and Polyamine Analogues: Chemical Synthesis and Biological Evaluation Integrated with Molecular Docking and 3-D QSAR Studies

Studies on lysozyme modifications induced by substituted p-benzoquinones

Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis

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