1874-54-0 Usage
Uses
Used in Pharmaceutical Industry:
Psicofuranine is used as an antibiotic and antitumor agent for its ability to inhibit xanthosine monophosphate aminase, which results in guanine deficiency in enteric bacteria. This property makes it a potential candidate for the development of treatments targeting bacterial infections and cancer cells.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 1874-54-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,7 and 4 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1874-54:
(6*1)+(5*8)+(4*7)+(3*4)+(2*5)+(1*4)=100
100 % 10 = 0
So 1874-54-0 is a valid CAS Registry Number.
InChI:InChI=1/C11H15N5O5/c12-9-6-10(14-3-13-9)16(4-15-6)11(2-18)8(20)7(19)5(1-17)21-11/h3-5,7-8,17-20H,1-2H2,(H2,12,13,14)
