Individual pKa Values of Tobramycin, Kanamycin B, Amikacin, Sisomicin, and Netilmicin Determined by Multinuclear NMR Spectroscopy

被引:26
作者
Alkhzem, Abdulaziz H. [1 ]
Woodman, Timothy J. [1 ]
Blagbrough, Ian S. [1 ]
机构
[1] Univ Bath, Dept Pharm & Pharmacol, Bath BA2 7AY, Avon, England
关键词
AMINOGLYCOSIDES; ANTIBIOTICS; POLYAMINES; BASE; ACID;
D O I
10.1021/acsomega.0c02744
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
NMR spectroscopy is a powerful technique for separating and measuring each distinct pK(a) value of the amino groups around aminoglycoside antibiotics. Unambiguous assignments were made for each individual amine substituent on 2-deoxystreptamine, tobramycin, kanamycin B, amikacin, sisomicin, and netilmicin using variations in the NMR spectroscopic chemical shift (delta) with H-1, C-13, and N-15 HMBC; the individual pK(a) values of netilmicin are reported for the first time.
引用
收藏
页码:21094 / 21103
页数:10
相关论文
共 23 条
[1]  
Armstrong ES, 2012, ANTIBIOTIC DISCOVERY AND DEVELOPMENT, VOLS 1 AND 2, P229, DOI 10.1007/978-1-4614-1400-1_7
[2]  
Beale J. M., 2010, ORGANIC MED PHARM CH, P294
[3]  
Blagbrough IS, 2011, METHODS MOL BIOL, V720, P493, DOI 10.1007/978-1-61779-034-8_32
[4]   Biologically important conformations of aminoglycoside antibiotics bound to an aminoglycoside 3'-phosphotransferase as determined by transferred nuclear Overhauser effect spectroscopy [J].
Cox, JR ;
Serpersu, EH .
BIOCHEMISTRY, 1997, 36 (09) :2353-2359
[5]   N-15 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY - NEBRAMYCIN AMINOGLYCOSIDES [J].
DORMAN, DE ;
PASCHAL, JW ;
MERKEL, KE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (22) :6885-6888
[6]   Synthesis of cholesteryl polyamine carbamates:: pKa studies and condensation of calf thymus DNA [J].
Geall, AJ ;
Taylor, RJ ;
Earll, ME ;
Eaton, MAW ;
Blagbrough, IS .
BIOCONJUGATE CHEMISTRY, 2000, 11 (03) :314-326
[7]   PREPARATION, PHYSICOCHEMICAL CHARACTERIZATION, AND RELAXOMETRY STUDIES OF VARIOUS GADOLINIUM(III)-DTPA-BIS(AMIDE) DERIVATIVES AS POTENTIAL MAGNETIC-RESONANCE CONTRAST AGENTS [J].
GERALDES, CFGC ;
URBANO, AM ;
ALPOIM, MC ;
SHERRY, AD ;
KUAN, KT ;
RAJAGOPALAN, R ;
MATON, F ;
MULLER, RN .
MAGNETIC RESONANCE IMAGING, 1995, 13 (03) :401-420
[8]   USE OF GLASS ELECTRODES TO MEASURE ACIDITIES IN DEUTERIUM OXIDE [J].
GLASOE, PK ;
LONG, FA .
JOURNAL OF PHYSICAL CHEMISTRY, 1960, 64 (01) :188-190
[9]  
Gunther H., 1980, BER BUNSEN PHYS CHEM, P368
[10]   Schiff base formation and recognition of amino sugars, aminoglycosides and biological polyamines by 2-formyl phenylboronic acid in aqueous solution [J].
Gutierrez-Moreno, Nini J. ;
Medrano, Felipe ;
Yatsimirsky, Anatoly K. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (34) :6960-6972