Mechanistic Studies on the Reaction between R2N-NONOates and Aquacobalamin: Evidence for Direct Transfer of a Nitroxyl Group from R2N-NONOates to Cobalt(III) Centers

被引:36
作者
Hassanin, Hanaa A. [1 ,2 ,3 ]
Hannibal, Luciana [4 ,5 ]
Jacobsen, Donald W. [4 ,5 ]
El-Shahat, Mohamed F. [3 ]
Hamza, Mohamed S. A. [3 ]
Brasch, Nicola E. [1 ,2 ]
机构
[1] Kent State Univ, Dept Chem, Kent, OH 44242 USA
[2] Kent State Univ, Sch Biomed Sci, Kent, OH 44242 USA
[3] Ain Shams Univ, Fac Sci, Dept Chem, Cairo, Egypt
[4] Kent State Univ, Sch Biomed Sci, Kent, OH 44242 USA
[5] Cleveland Clin, Lerner Res Inst, Dept Cell Biol, Cleveland, OH 44195 USA
基金
美国国家科学基金会;
关键词
cobalamins; kinetics; nitroxyl complexes; N; O ligands; vitamins; NITRIC-OXIDE RELEASE; ANTILEUKEMIC ACTIVITY; ANTICANCER LEAD; NO; COMPLEXES; CHEMISTRY; KINETICS; PRODRUGS; ANALOGS; BINDING;
D O I
10.1002/anie.200904360
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tales of the unexpected: Transfer of a nitroxyl group from R2N-NONOates to aquacobalamin to form nitroxylcobaiamin does not proceed via H+-catalyzed R2NNONOate decomposition, but instead occurs via a probable NONOate-cobalamin intermediate (see scheme; r.d.s.=rate-determining step). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:8909 / 8913
页数:5
相关论文
共 38 条
[1]   Nitric oxide (NO) - Biogeneration, regulation, and relevence to human diseases [J].
Bian, K ;
Murad, F .
FRONTIERS IN BIOSCIENCE-LANDMARK, 2003, 8 :D264-D278
[2]   A simple, convenient and direct method for assessing the purity of cobalamins [J].
Brasch, NE ;
Finke, RG .
JOURNAL OF INORGANIC BIOCHEMISTRY, 1999, 73 (04) :215-219
[3]   Cell-Permeable Esters of Diazeniumdiolate-Based Nitric Oxide Prodrugs [J].
Chakrapani, Harinath ;
Maciag, Anna E. ;
Citro, Michael L. ;
Keefer, Larry K. ;
Saavedra, Joseph E. .
ORGANIC LETTERS, 2008, 10 (22) :5155-5158
[4]   Synthesis, nitric oxide release, and anti-leukemic activity of glutathione-activated nitric oxide prodrugs: Structural analogues of PABA/NO, an anti-cancer lead compound [J].
Chakrapani, Harinath ;
Wilde, Thomas C. ;
Citro, Michael L. ;
Goodblatt, Michael M. ;
Keefer, Larry K. ;
Saavedra, Joseph E. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (05) :2657-2664
[5]   Synthesis and in vitro anti-leukemic activity analogues of JS']JS-K, an anti-cancer lead of structural compound [J].
Chakrapani, Harinath ;
Goodblatt, Michael M. ;
Udupi, Vidya ;
Malaviya, Swati ;
Shami, Paul J. ;
Keefer, Larry K. ;
Saavedra, Joseph E. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (03) :950-953
[6]   Chemistry of the diazeniumdiolates. 2. Kinetics and mechanism of dissociation to nitric oxide in aqueous solution [J].
Davies, KM ;
Wink, DA ;
Saavedra, JE ;
Keefer, LK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (23) :5473-5481
[7]   BEITRAGE ZUR CHEMIE UND BIOCHEMIE DER COBALAMINE .2. UBER DEN ABBAU DER COBALAMINE MIT CER(III)-HYDROXYD 7-[D-RIBOFURANOSIDO]-ADENIN EINABBAUPRODUKT DES PSEUDOVITAMINS-B12 [J].
FRIEDRICH, W ;
BERNHAUER, K .
CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (11) :2507-2512
[8]  
Hannibal L., 2007, ANGEW CHEM, V119, P5232
[9]   Nitroxylcob (III) alamin: Synthesis and X-ray structural characterization [J].
Hannibal, Luciana ;
Smith, Clyde A. ;
Jacobsen, Donald W. ;
Brasch, Nicola E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) :5140-5143
[10]   Release of nitric oxide from novel diazeniumdiolates monitored by laser magnetic resonance spectroscopy [J].
Horstmann, A ;
Menzel, L ;
Gäbler, R ;
Jentsch, A ;
Urban, W ;
Lehmann, J .
NITRIC OXIDE-BIOLOGY AND CHEMISTRY, 2002, 6 (02) :135-141