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Water-soluble metalloporphyrins as models of hemoproteins and peroxynitrite decomposition catalysts.
紀錄類型:
書目-電子資源 : Monograph/item
正題名/作者:
Water-soluble metalloporphyrins as models of hemoproteins and peroxynitrite decomposition catalysts.
作者:
Zhou, Huchen.
面頁冊數:
155 p.
附註:
Adviser: John T. Groves.
附註:
Source: Dissertation Abstracts International, Volume: 64-08, Section: B, page: 3833.
Contained By:
Dissertation Abstracts International64-08B.
標題:
Chemistry, Organic.
電子資源:
http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3103024
ISBN:
0496505939
Water-soluble metalloporphyrins as models of hemoproteins and peroxynitrite decomposition catalysts.
Zhou, Huchen.
Water-soluble metalloporphyrins as models of hemoproteins and peroxynitrite decomposition catalysts.
[electronic resource] - 155 p.
Adviser: John T. Groves.
Thesis (Ph.D.)--Princeton University, 2003.
A highly sensitive fluorescent probe, 6A-N-dansyl-permethylated-beta-cyclodextrin, formed 2:1 complexes with manganese(III) meso-tetrakis(4-carboxyphenyl) porphyrin (Mn(III)TCPP), manganese(III) meso-tetrakis(4-sulfonatophenyl) porphyrin (Mn(III)TPPS) and manganese(III) meso-tetrakis(2,3,5,6-tetrafluoro-N,N,N-trimethyl-4-aniliniumyl) porphyrin with binding constants of 6.1 x 109 M-2, 7.1 x 1010 M-2 , and 1.6 x 1011 M-2 as determined by fluorescence titrations. This made possible the reliable measurement of weak binding constants. As shown by 1H-NMR and UV-Vis, a novel PEGylated cyclodextrin, Heptakis(2,3,6-tri-O-2-(2-(2-methoxyethoxy)ethoxy)ethyl)-beta-cyclodextrin formed 1:1 complexes with Mn(III)TCPP and H2TCPP (meso -tetrakis(4-carboxyphenyl) porphyrin) with binding constants of 1.2 x 106 M-1 and ≥108 M-1 that was the highest for a monomeric cyclodextrin. On the contrary, heptakis(2,6-di-O-methyl-3-O-2-(2-(2-methoxyethoxy)ethoxy)ethyl)-beta-cyclodextrin bound porphyrins with a 2:1 mode. Based on the successful control of binding mode, Hemodextrin, a self-assembled construct between Fe(III)TPPS and py-PPCD (2A-O-(3-pyridylmethyl)-perPEGylated beta-cyclodextrin) has been built. The binding constant was 2 x 106 M -1 and the pyridyl nitrogen of py-PPCD was shown to ligate to iron by 1H-NMR and UV-Vis. This hemodextrin ensemble has been shown to bind dioxygen reversibly and to form a stable ferryl species. This is the first self-assemble synthetic functional hemoprotein model compound.
ISBN: 0496505939Subjects--Topical Terms:
193634
Chemistry, Organic.
Water-soluble metalloporphyrins as models of hemoproteins and peroxynitrite decomposition catalysts.
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A highly sensitive fluorescent probe, 6A-N-dansyl-permethylated-beta-cyclodextrin, formed 2:1 complexes with manganese(III) meso-tetrakis(4-carboxyphenyl) porphyrin (Mn(III)TCPP), manganese(III) meso-tetrakis(4-sulfonatophenyl) porphyrin (Mn(III)TPPS) and manganese(III) meso-tetrakis(2,3,5,6-tetrafluoro-N,N,N-trimethyl-4-aniliniumyl) porphyrin with binding constants of 6.1 x 109 M-2, 7.1 x 1010 M-2 , and 1.6 x 1011 M-2 as determined by fluorescence titrations. This made possible the reliable measurement of weak binding constants. As shown by 1H-NMR and UV-Vis, a novel PEGylated cyclodextrin, Heptakis(2,3,6-tri-O-2-(2-(2-methoxyethoxy)ethoxy)ethyl)-beta-cyclodextrin formed 1:1 complexes with Mn(III)TCPP and H2TCPP (meso -tetrakis(4-carboxyphenyl) porphyrin) with binding constants of 1.2 x 106 M-1 and ≥108 M-1 that was the highest for a monomeric cyclodextrin. On the contrary, heptakis(2,6-di-O-methyl-3-O-2-(2-(2-methoxyethoxy)ethoxy)ethyl)-beta-cyclodextrin bound porphyrins with a 2:1 mode. Based on the successful control of binding mode, Hemodextrin, a self-assembled construct between Fe(III)TPPS and py-PPCD (2A-O-(3-pyridylmethyl)-perPEGylated beta-cyclodextrin) has been built. The binding constant was 2 x 106 M -1 and the pyridyl nitrogen of py-PPCD was shown to ligate to iron by 1H-NMR and UV-Vis. This hemodextrin ensemble has been shown to bind dioxygen reversibly and to form a stable ferryl species. This is the first self-assemble synthetic functional hemoprotein model compound.
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As a nitric oxide synthase model, iron(III) tetrakis(N-methyl-2-pyridyl)porphyrin (Fe(III)P) catalyzed the unprecedented aerobic oxidation of NG-Hydroxy-L-Arginine in buffers at 25°C. N-nitrosoarginine and Ndelta-cyanoornithine were produced at pH 7.4, while Ndelta-cyanoornithine and nitrite/nitrate were the major products at pH 11. At pH = 3 or 5, there was no significant reaction. A new species at 420 nm appeared upon mixing NHA with Fe(III)P at pH 9 or 11 and was tentatively assigned to Fe(III)P-NHA complex. The oxidation is proposed to be initiated by a homolytic cleavage of the Fe-O bond.
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The second generation of cationic porphyrinic peroxynitrite decay catalysts have been synthesized. The atropisomer-free iron(III) meso-tetrakis(N,N-di-(2-(2-methoxyethoxy)ethyl)-imidazol-2-yl)porphyrin and iron(III) meso-tetrakis(N,N-dicarboxymethyl)-imidazol-2-yl)porphyrin are of great pharmacological significance as potent peroxynitrite decomposition catalysts in vitro and in vivo.
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