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MedKoo Cat#: 591122 | Name: Psicofuranine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Psicofuranine is an antibiotic and antitumor compound. Psicofuranine specifically inhibits GMP synthase and interrupts parasite growth.

Chemical Structure

Psicofuranine
Psicofuranine
CAS# 1874-54-0

Theoretical Analysis

MedKoo Cat#: 591122

Name: Psicofuranine

CAS#: 1874-54-0

Chemical Formula: C11H5N5O5

Exact Mass: 297.1073

Molecular Weight: 297.27

Elemental Analysis: C, 44.44; H, 5.09; N, 23.56; O, 26.91

Price and Availability

Size Price Availability Quantity
1mg USD 500.00 2 weeks
5mg USD 1,025.00 2 weeks
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Related CAS #
No Data
Synonym
Psicofuranine; NSC 53104; NSC-53104; NSC53104; Angustmycin C
IUPAC/Chemical Name
Adenine, 9-beta-D-psicofuranosyl-
InChi Key
BNZYRKVSCLSXSJ-IOSLPCCCSA-N
InChi Code
InChI=1S/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)/t5-,7-,8-,11-/m1/s1
SMILES Code
NC1=C2C(N([C@@]3(CO)[C@@H]([C@@H]([C@@H](CO)O3)O)O)C=N2)=NC=N1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Psicofuranine acts as an inhibitor of xanthosine monophosphate (XMP) aminase (IC50 = 67 µM), causing guanine deficiency in enteric bacteria.
In vitro activity:
Psicofuranine disrupted Plasmodium falciparum growth by targeting GMP synthase, which plays a crucial role in guanylate nucleotide biosynthesis. Psicofuranine has potential as an inhibitor of purine salvage in malaria parasites. Reference: Exp Parasitol. 2000 Jan;94(1):23-32. https://pubmed.ncbi.nlm.nih.gov/10631077/
In vivo activity:
To be determined
Solvent mg/mL mM
Solubility
DMSO 50.0 168.20
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 297.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. McConkey GA. Plasmodium falciparum: isolation and characterisation of a gene encoding protozoan GMP synthase. Exp Parasitol. 2000 Jan;94(1):23-32. doi: 10.1006/expr.1999.4467. PMID: 10631077. 2. Rohlman CE, Matthews RG. Role of purine biosynthetic intermediates in response to folate stress in Escherichia coli. J Bacteriol. 1990 Dec;172(12):7200-10. doi: 10.1128/jb.172.12.7200-7210.1990. PMID: 2254281; PMCID: PMC210845.
In vitro protocol:
1. McConkey GA. Plasmodium falciparum: isolation and characterisation of a gene encoding protozoan GMP synthase. Exp Parasitol. 2000 Jan;94(1):23-32. doi: 10.1006/expr.1999.4467. PMID: 10631077. 2. Rohlman CE, Matthews RG. Role of purine biosynthetic intermediates in response to folate stress in Escherichia coli. J Bacteriol. 1990 Dec;172(12):7200-10. doi: 10.1128/jb.172.12.7200-7210.1990. PMID: 2254281; PMCID: PMC210845.
In vivo protocol:
To be determined
1: Shi Y, Pan X, Wu X, Xu J, Xiang W, Zheng Y, Dong F, Wang X. Uptake and Biotransformation of Guvermectin in Three Crops after In Vivo and In Vitro Exposure. J Agric Food Chem. 2024 May 15;72(19):10842-10852. doi: 10.1021/acs.jafc.4c01320. Epub 2024 May 6. PMID: 38708761. 2: Liu C, Wang Z, Chen Y, Yan Y, Li L, Wang YJ, Bai L, Li S, Zhang Y, Wang X, Huang SX, Xiang W. Guvermectin Biosynthesis Revealing the Key Role of a Phosphoribohydrolase and Structural Insight into the Active Glutamate of a Noncanonical Adenine Phosphoribosyltransferase. ACS Chem Biol. 2023 Jan 20;18(1):102-111. doi: 10.1021/acschembio.2c00739. Epub 2023 Jan 9. PMID: 36623177. 3: McConkey GA. Plasmodium falciparum: isolation and characterisation of a gene encoding protozoan GMP synthase. Exp Parasitol. 2000 Jan;94(1):23-32. doi: 10.1006/expr.1999.4467. PMID: 10631077. 4: Katagiri N, Nomura M, Sato H, Tameda C, Kurimoto A, Arai S, Toyota A, Kaneko C. Synthesis of purine bases having a di(hydroxymethyl)cyclopentenyl group by means of high-pressure reaction and their anti-HIV activity. Nucleic Acids Symp Ser. 1991;(25):5-6. PMID: 1842092. 5: Rohlman CE, Matthews RG. Role of purine biosynthetic intermediates in response to folate stress in Escherichia coli. J Bacteriol. 1990 Dec;172(12):7200-10. doi: 10.1128/jb.172.12.7200-7210.1990. PMID: 2254281; PMCID: PMC210845. 6: Marquez VE, Bodenteich M, Copp RR Jr, Lim BB. Synthesis and biological activity of novel carbocyclic nucleosides. Nucleic Acids Symp Ser. 1990;(22):35-6. PMID: 2101908. 7: von der Saal W, Crysler CS, Villafranca JJ. Positional isotope exchange and kinetic experiments with Escherichia coli guanosine-5'-monophosphate synthetase. Biochemistry. 1985 Sep 24;24(20):5343-50. doi: 10.1021/bi00341a011. PMID: 3907701. 8: Rosenthal A, Ratcliffe M. C4'-Branched-chain surgar nucleosides: synthesis of isomers of psicofuranine. Carbohydr Res. 1977 Mar;54(1):61-73. doi: 10.1016/s0008-6215(00)80556-x. PMID: 861968. 9: Patel N, Moyed HS, Kane JF. Xanthosine-5'-phosphate amidotransferase from Escherichia coli. J Biol Chem. 1975 Apr 10;250(7):2609-13. PMID: 235520. 10: 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. PMID: 5332732. 11: Forist AA. Biological half-life of psicofuranine in the human. J Pharm Sci. 1965 Jun;54(6):927. doi: 10.1002/jps.2600540630. PMID: 5847035. 12: SUGIMORI T, SUHADOLNIK RJ. THE BIOSYNTHESIS OF PSICOFURANINE. J Am Chem Soc. 1965 Mar 5;87:1136-7. doi: 10.1021/ja01083a038. PMID: 14284629. 13: UDAKA S, MOYED HS. INHIBITION OF PARENTAL AND MUTANT XANTHOSINE 5'-PHOSPHATE AMINASES BY PSICOFURANINE. J Biol Chem. 1963 Aug;238:2797-803. PMID: 14063305. 14: DESSI P, RIZZOLI C, CESTARI A. AZIONE DELLA PSICOFURANINA SUGLI ELEMENTI TUMORALI UMANI IN COLTURA PERENNE [ACTION OF PSICOFURANINE ON HUMAN TUMORAL ELEMENTS IN CONTINUOUS CULTURE]. Arch Ital Sci Farmacol. 1963 Apr;13:175-6. Italian. PMID: 14245136. 15: TALLEY RW, CARLSON RG. Polyserositis induced by psicofuranine in man and comparative toxicity in the rat, mouse, chicken, and monkey. Toxicol Appl Pharmacol. 1963 Mar;5:235-46. doi: 10.1016/0041-008x(63)90046-2. PMID: 13984785. 16: COSTA G, HOLLAND JF, PICKREN JW. Acute pericarditis produced by psicofuranine, a nucleoside analogue. N Engl J Med. 1961 Dec 7;265:1143-6. doi: 10.1056/NEJM196112072652305. PMID: 13881576. 17: MAGEE WE, EBERTS FS Jr. Studies with psicofuranine in the tumor-bearing rat. Cancer Res. 1961 Jun;21:611-9. PMID: 13765193. 18: SLECHTA L. Studies on the mode of action of psicofuranine. Biochem Pharmacol. 1960 Oct;5:96-107. doi: 10.1016/0006-2952(60)90013-7. PMID: 13913839. 19: GARRETT ER, THOMAS RC, WALLACH DP, ALWAY CD. Psicofuranine: kinetics and mechanisms in vivo with the application of the analog computer. J Pharmacol Exp Ther. 1960 Sep;130:106-18. PMID: 13703731. 20: HANKA LJ, BURCH MR. Improved assay for psicofuranine. Antibiot Chemother (Northfield). 1960 Aug;10:484-7. PMID: 13851898.