It is well recognized that pH plays a significant regulatory role in most cellular processes. Increasingly, there is interest in transmembrane pH gradients, particularly with respect to tumor growth and response to therapy. NMR offers a non-invasive approach to monitoring cellular pH and detecting changes in response to interventions. This review will consider the strengths of various approaches to measuring pH with particular focus on the reporter molecules designed to interrogate the cellular milieu. In particular, fluorinated vitamin 86 derivatives (6-fluoropyridoxol and 6-fluoropyridoxamine) will be described, which for the first time provide a practical non-destructive method to measure simultaneously intra- and extracellular pH, i.e., the transmembrane pH gradient in animals in vivo based on a single reporter molecule. *In honor of the 75th birthday of Dr. John H. Mason, a lifelong advocate of non-destructive testing.

01 Aug 1994·FEBS LettersQ3 · BIOLOGY

6‐Fluoropyridoxol: A novel probe of cellular pH using ¹⁹F NMR spectroscopy

Q3 · BIOLOGY

Article

Author: Aravind, Sivasubramanian ; Antich, Peter P. ; Constantinescu, Anca ; Mason, Ralph P. ; Goomer, Naresh ; Kulkarni, Padmakar V. ; Mehta, Vimal D.

6‐Fluoropyridoxol was evaluated as an intracellular pH indicator. This molecule exhibits exceptional sensitivity to changes in pH (∼ 10 ppm acid/base shift) and a pKa ∼8.2 appropriate for physiological investigations. Using 19F NMR spectroscopy we determined both intra‐ and extracellular pH in whole blood and confirmed the measurements using traditional techniques: ion‐electrodes and 31P NMR spectroscopy.

01 Jun 1973·Journal of Medicinal ChemistryQ1 · MEDICINE

Chemistry and biology of vitamin B6. 31. Synthesis and physicochemical and biological properties of 6-halogen-substituted vitamin B6 analogs

Q1 · MEDICINE

Article

Author: Srivastava, S. C. ; Korytnyk, W.

The presence of a 6-halogen atom in vitamin B6 analogs radically changed their phys.-chem. properties, especially pKa values, resulting in a loss of zwitterionic character and assumption of a hydrophobic character.All 6-fluoro analogs inhibited growth in vitro of mouse mammary adenocarcinoma and sarcoma 180 cells, the most potent compound being 6-fluoropyridoxal oxime (I) [42242-38-6], but were ineffective in the presence of 10-5 M pyridoxal [66-72-8].I and 6-chloropyridoxol [15741-67-0] were potent convulsants in mice, causing 100% mortality at 50 and 100 mg/kg, resp.I was prepared from 6-aminopyridoxol [42242-40-0] by a modified Schiemann reaction yielding 6-fluoropyridoxol [42242-41-1], which was selectively oxidized with MnO2 to 6-fluoropyridoxal [42242-42-2] and treated with NH2OH.HCl.6-Chloropyridoxol, the intermediate in preparation of chlorinated derivatives, was prepared by chlorination of α4,α5-O-isopropylidenepyridoxol [948-00-5] with Me3COCl and acid hydrolysis.6-Fluoropyridoxamine phosphate [42242-44-4] was a potent inhibitor in vitro of pyridoxine phosphate oxidase [9029-21-4], the enzyme catalyzing formation of pyridoxal phosphate.

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