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rdf:type |
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lifeskim:mentions |
umls-concept:C0002508,
umls-concept:C0021212,
umls-concept:C0024485,
umls-concept:C0034326,
umls-concept:C0042295,
umls-concept:C0205250,
umls-concept:C0205251,
umls-concept:C0220806,
umls-concept:C0330390,
umls-concept:C0332324,
umls-concept:C0333051,
umls-concept:C0456387,
umls-concept:C0542341,
umls-concept:C0870071,
umls-concept:C1407029,
umls-concept:C1553628,
umls-concept:C2003941
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pubmed:issue |
26
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pubmed:dateCreated |
2000-8-10
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pubmed:abstractText |
Fourteen linear and cyclic alpha- and beta-aminophosphonates in which the P-atom is substituted by alkoxy groups have been synthesized and evaluated as (31)P NMR pH markers in Krebs-Henseleit buffer. pK(a) values varied with substitution in the range 1.3-9.1, giving potentially access to a wide range of pH. Temperature had a weak influence on pH and a dramatic increase in ionic strength slightly modified the pK(a) of the pyrrolidine diethyl(2-methylpyrrolidin-2-yl)phosphonate (DEPMPH). All compounds displayed a 4-fold better NMR sensitivity than inorganic phosphate or other commonly used phosphonates, as assessed by differences delta(b)-delta(a) between the chemical shifts of the protonated and the unprotonated forms. In isolated perfused rat hearts, a non-toxic concentration window of 1.5-15 mm was determined for three representative compounds. Using empirical linear relationships, the experimental values of pK(a), delta(a), and delta(b) have been correlated with the two-dimensional structure, i.e. the chemical nature of substituents bonded to the secondary amine and P-atom. The data suggest that DEPMPH and its cyclic and linear variants are ideal versatile (31)P NMR probes for the study of tenuous pH changes in biological processes.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Jun
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pubmed:issn |
0021-9258
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
30
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pubmed:volume |
275
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
19505-12
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pubmed:dateRevised |
2009-11-3
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pubmed:meshHeading |
pubmed-meshheading:10748044-Amines,
pubmed-meshheading:10748044-Animals,
pubmed-meshheading:10748044-Dose-Response Relationship, Drug,
pubmed-meshheading:10748044-Heart,
pubmed-meshheading:10748044-Hydrogen-Ion Concentration,
pubmed-meshheading:10748044-Indicators and Reagents,
pubmed-meshheading:10748044-Kinetics,
pubmed-meshheading:10748044-Magnetic Resonance Spectroscopy,
pubmed-meshheading:10748044-Male,
pubmed-meshheading:10748044-Models, Statistical,
pubmed-meshheading:10748044-Myocardium,
pubmed-meshheading:10748044-Perfusion,
pubmed-meshheading:10748044-Phosphonic Acids,
pubmed-meshheading:10748044-Phosphorus Isotopes,
pubmed-meshheading:10748044-Phosphorylation,
pubmed-meshheading:10748044-Protein Conformation,
pubmed-meshheading:10748044-Protein Structure, Tertiary,
pubmed-meshheading:10748044-Pyrrolidines,
pubmed-meshheading:10748044-Rats,
pubmed-meshheading:10748044-Rats, Wistar,
pubmed-meshheading:10748044-Reproducibility of Results,
pubmed-meshheading:10748044-Sensitivity and Specificity,
pubmed-meshheading:10748044-Spin Labels,
pubmed-meshheading:10748044-Temperature
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pubmed:year |
2000
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pubmed:articleTitle |
alpha - and beta -phosphorylated amines and pyrrolidines, a new class of low toxic highly sensitive 31P NMR pH indicators. Modeling of pKa and chemical shift values as a function of substituents.
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pubmed:affiliation |
Structure et Réactivité des Espèces Paramagnétiques, CNRS-UMR 6517, France. pietri@srepir1.univ-mrs.fr
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pubmed:publicationType |
Journal Article
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