Development of novel 19 F NMR pH indicators: synthesis and evaluation of a series of fluorinated vitamin B 6 analogues

S He, RP Mason, S Hunjan, VD Mehta, V Arora…

Index: He, Sha; Mason, Ralph P.; Hunjan, Sandeep; Mehta, Vimal D.; Arora, Veera; Katipally, Revathi; Kulkarni, Padmakar V.; Antich, Peter P. Bioorganic and Medicinal Chemistry, 1998 , vol. 6, # 9 p. 1631 - 1639

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Citation Number: 21

Abstract

We have synthesized a series of novel fluorinated vitamin B6 analogues (6-fluoropyridoxol derivatives) as potential 19F NMR pH indicators for use in vivo. Modifications included addition of aldehyde, carboxyl or aminomethyl groups at the 4-or 5-ring position, and examination of a trifluoromethyl moiety as an internal chemical shift standard. The variation in chemical shift with respect to acid–base titration showed pKa values in the range 7.05– ...