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Synthesis and Interfacial Assembly of Chiral Macrocyclic Polyamine-Mn(Ⅱ) Complexes and Their Superoxide Dismutation Ability

Author: LiuPing
Tutor: ZhangAiDong；TuHaiYang
School: Central China Normal University
Course: Organic Chemistry
Keywords: Chiral macrocyclic polyamine manganese ( II ) complexes Interfacial assembly Axial ligand exchange Cyclic voltammetry AC impedance spectroscopy Superoxide anion
CLC: O641.4
Type: Master's thesis
Year: 2007
Downloads: 101
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Abstract


Superoxide dismutase (superoxide dismutase, SOD) is a metal ubiquitous enzyme in vivo, can effectively control and maintain normal vivo superoxide anion (O 2 - ) concentration. The design and synthesis of superoxide dismutase SOD function model compounds (Model compound of Superoxide dismutase, MSOD), high stability, low toxicity, low cost, and molecular characteristics of small significance in the pharmaceutical and clinical applications. The design and synthesis of a chiral macrocyclic polyamine metal complexes with SOD activity, instead of natural SOD interfacial molecular assembly, prepared Biomimetic biosensor SOD, superoxide anion radical detection will have a long life and repeatability of higher production significant advantages of superoxide anion concentration disease diagnostic tests, has important applications in clinical practice. This article is designed and synthesized a series of new chiral macrocyclic polyamine manganese (II) complexes, built at the gold electrode interface the SOD mimetic enzyme molecules assembled system, electrochemical methods and X-ray photoelectron spectroscopy (XPS) its structure and properties of the study, measured its disproportionation of the superoxide anion. The main contents are as follows: 1. Imidazole derivative synthesized a series of [15]-ane-N 5 as the basic skeleton of chiral macrocyclic polyamines manganese (II) complexes, as well as the interface assembly and metal ion coordination function substance lipoic acid histamine (imid-2S). The molecular structure of the target compounds and some intermediates 1 HNMR, GC-MS, ESI-MS, IR and UV, etc. were confirmed: (?) 2. Tried in the imid-2S self-assembled film interface through its imidazolyl and Mn-01 axial Cl -1 ligand exchange interface fixing metal complexes of macrocyclic polyamine. Using electrochemical impedance spectroscopy and cyclic voltammetry study the macrocyclic polyamine manganese (II) complexes Mn-01 axial Cl -1 ligand imid-2S self-assembled film electrode interface on the axial ligand exchange behavior, experimental results show that by the axial ligand exchange macrocyclic polyamine metal complexes in self-assembled membrane fixed, and the surface concentration of Mn-01 1.45 × 10 -11 mol · cm -2 . Solution complexes Mn-01 axial Cl -1 ligand imid-2S ligand exchange before and after UV-visible absorption spectroscopy no significant change, probably because of this type of macrocyclic polyamine metal the complex axial ligand is weak coordination, exchange of ligands on the metal ion ligand field change has little effect. 3. Be prepared by the self-assembly technology by the head group of the α-lipoic acid-containing macrocyclic polyamine complexes Mn-07/Au modified electrodes. Electrochemical impedance spectroscopy and cyclic voltammetry experiment results show that the self-assembled monolayer coverage reached 99.65%, the surface concentration of of 1.32 × -10 mol · cm -2 . When the to change scan cyclic voltammetry detection rate, Mn-07/Au modified electrode redox peak potential remained basically unchanged, the redox peak current increases with increasing scan rate and showed a good linear relationship, that Mn-07 on a gold electrode surface to form dense self-assembled monolayer. The results are further confirmed this conclusion by X-ray photoelectron spectroscopy (XPS) Mn-07/Au modified electrode characterization. 4. Xanthine - xanthine oxidase system to produce O 2 - , macrocyclic polyamine complexes containing α-lipoic acid head groups Mn-07/Au molecular assembly system with O 2 - of interaction, the results show that these proposed enzyme molecules assembled system has obvious catalytic superoxide anion radical disproportionation and possible reaction mechanism of the catalytic disproportionation process. Macrocyclic polyamine complexes can not be directly assembled on the gold electrode surface, the selection of Mn-02, of Mn-04, Mn-06, represented by the SOD-like activity were measured with classic orthophthalic three autoxidation method get their inhibition rates were 14.75%, 9.01% and 0.82% respectively.

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CLC: > Mathematical sciences and chemical > Chemistry > Physical Chemistry ( theoretical chemistry ),chemical physics > Structural Chemistry > Complex chemistry ( coordination chemistry )
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