Uses
Psicofuranine is a nucleoside antibiotic shown to inhibit xanthosine monophosphate aminase.
Uses
Psicofuranine is an antibiotic and antitumor compound that acts as an inhibitor of xanthosine monophosphate (XMP) aminase (IC50 = 67 μM), causing guanine deficiency in enteric bacteria.[Cayman Chemical]
Definition
ChEBI: Psicofuranin is a purine nucleoside and a psicose derivative.
Biological Activity
psicofuranine is an antibiotic that acts as an inhibitor of xanthosine 5’-phosphate (xmp) aminase with ic50 value of 67 μm [1][2][3].xanthosine 5’-phosphate (xmp) aminase is an enzyme essential for guanine nucleotide synthesis and possess catalytic activity with either glutamine or ammonia as a substrate [2][3].psicofuranine (9-n-psicofuranosy-6-aminopurine) is an antibiotic that acts as an inhibitor of xanthosine 5’-phosphate (xmp) aminase with ic50 value of 67 μm. in unfractionated preparations of both strains b-24 and b-35-2, 6.7 x 10-5m psicofuranin inhibited 50% xmp aminase after 2 minutes. psicofuranine caused a guanine deficiency in enteric bacteria by inhibition of xmp aminase [2]. psicofuranine-inhibited aminase couldn’t catalyze the aminolysis of the preformed intermediate to amp and gmp, nor could it condense atp and xmp to form the intermediate [3]. psicofuranine had good antibacterial activity in vivo and antitumor activity [1].
Enzyme inhibitor
This adenosine analogue (FW = 297.27 g/mol; CAS 1874-54-0), also known as 6-amino-9-D-psicofuranosylpurine, 9b-D-(psicofuranosyl)- adenine, and angustmycin C, is a nucleoside antibiotic isolated from Streptomyces hygroscopicus that also exhibits antitumor activity. Psicofuranine is soluble in water (8 mg/mL at 25°C) and has a lmax value of 261 nm in 10 mM base or 259 nm in 10 mM acid. Psicofuranine is an irreversible inhibitor of GMP synthetase that acts by preventing the release (or further reaction) of adenyl-XMP with water or ammonia; however, it does not suppress exchange reactions. Target(s): deoxycytidine kinase, weakly inhibited, Ki = 12 mM; GMP synthetase, or XMP aminase (2- 11); and NAD+ synthetase.
References
[1]. ladislav j. hanka. mechanism of action of psicofuranine. j bacteriol. 1960 jul; 80(1): 30–36.
[2]. udaka s, moyed hs. inhibition of parental and mutant xanthosine 5'-phosphate aminases by psicofuranine. j biol chem. 1963 aug;238:2797-803.
[3]. fukuyama tt. formation of an adenyl xanthosine monophosphate intermediate by xanthosine 5'-phosphate aminase and its inhibition by psicofuranine. j biol chem. 1966 oct 25;241(20):4745-9.
