[Study of the stability of pyrimido-[5,4-e]-1,2,4-triazine antibiotics in acid-base media by NMR spectroscopy].
A comparative study of the NMR 1H and 13C spectra of reumycin, fervenulin and xanthothricin in aqueous acid-base media showed that at pH or pD ranging from 8.0 to 1.0 the antibiotics were chemically stable. By the ratio of the 1H and 13C chemical shifts of reumycin at pH 4.0-10.0 the pKa values of this antibiotic were determined: 6.7 in aqueous (D2O) solution and 8.76 in dimethylsulfoxide media. Alkalization of the solutions of reumycin (pH 12.0), fervenulin (pH 9.0) and xanthothricin (pH 8.0) resulted in irreversible chemical transformation of the antibiotics. The analysis of the chemical shifts in the PMR spectra of the transformation products revealed transformation of the uracil ring in reumycin and uracil and triazine rings in fervenulin and xanthothricin. Alkalization of the xanthothricin solutions resulted also in demethylation with formation of reumycin.
D000900:Anti-Bacterial Agents / Q000032:analysis*; D055598:Chemical Phenomena; D002621:Chemistry; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D011744:Pyrimidinones / Q000032:analysis; D013057:Spectrum Analysis; D014227:Triazines / Q000032:analysis
D000900:Anti-Bacterial Agents; D011744:Pyrimidinones; D014227:Triazines; C007721:fervenulin; C009169:reumycin; C009570:toxoflavin
Izuchenie ustoĭchivosti pirimido-[5,4-e]-1,2,4-triazinovykh antibiotikov v kislotno-osnovnykh sredakh metodom spektroskopii IaMR.