Synthesis, structure, and X-band (9.5 GHz) EPR characterization of the new series of pH-sensitive spin probes: N,N-disubstituted 4-amino-2,2,5,5-tetramethyl-3-imidazoline 1-oxyls.
Synthesis, structure, and X-band (9.5 GHz) EPR characterization of the new series of pH-sensitive spin probes: N,N-disubstituted 4-amino-2,2,5,5-tetramethyl-3-imidazoline 1-oxyls.
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新系列 pH 敏感自旋探针的合成、结构和 X 波段 (9.5 GHz) EPR 表征:N,N-二取代 4-氨基-2,2,5,5-四甲基-3-咪唑啉 1-oxyls
DOI:
10.1021/jo0510890
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发表时间:
2005
期刊:
影响因子:
--
通讯作者:
Grigor'ev,IgorA
中科院分区:
文献类型:
--
作者:
Voinov,MaximA;Polienko,JulyaF;Schanding,Thomas;Bobko,AndreyA;Khramtsov,ValeryV;Gatilov,YuryV;Rybalova,TatyanaV;Smirnov,AlexI;Grigor'ev,IgorA
An approach to the synthesis of new imidazoline nitroxides bearing anN‘,N‘-disubstituted amidine group is reported. The approach is based on the alkylation of diamagnetic 4-R-amino-1,2,2,5,5-pentamethyl-3-imidazolines with bromoacetic acid ethyl ester; the products of alkylation are further oxidized to the corresponding nitroxides. The approach allows a variety of functional groups to be introduced into the nitroxide molecule structure. Alkylation with bromoacetic acid ethyl ester was found to proceed with high regioselectivity and afford the products ofexo-alkylation. The regiochemical assignment is made on the basis of13C NMR spectra and confirmed by X-ray diffraction study. All of the nitroxides synthesized here were shown to have pH-dependent EPR spectra with pKaranging from 3.5 to 6.2. For nitroxides13bearing the carboxylic group remote to the nitroxide moiety, the changes in isotropic magnetic parameters of EPR spectra due to reversible deprotonation of the carboxylic group were found to be small. For these nitroxides, we demonstrate an alternative approach for pKadetermination that is based on measuring the peak-to-peak line width of the EPR spectrum in the presence of the paramagnetic broadening agent potassium ferricyanide. The partition coefficients of nitroxides in octanol/H2O and octanol/phosphate buffer solution mixtures were measured to reveal a range of their lipophilicities.
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DOI:
10.1016/s0021-9258(17)39825-3
发表时间:
1984
期刊:
The Journal of biological chemistry
影响因子:
--
作者:
B. Tuana;D. Maclennan
通讯作者:
D. Maclennan
DOI:
10.1016/b978-0-12-152831-7.50007-x
发表时间:
1990
期刊:
Current topics in cellular regulation
影响因子:
--
作者:
Colbran,RJ;Soderling,TR
通讯作者:
Soderling,TR
影响因子:
2.8
作者:
W. Nayler;S. Panagiotopoulos;J. S. Elz;W. J. Sturrock
通讯作者:
W. J. Sturrock
DOI:
--
发表时间:
1986
期刊:
The Journal of thoracic and cardiovascular surgery
影响因子:
--
作者:
Otani,H;Engelman,RM;Breyer,RH;Rousou,JA;Lemeshow,S;Das,DK
通讯作者:
Das,DK
影响因子:
2.8
作者:
A. Katz;H. Reuter
通讯作者:
H. Reuter