Psicofuranine | CAS# 1874-54-0 | bioactive chemical

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

MedKoo CAT#: 591122

CAS#: 1874-54-0

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

Chemical Structure

Psicofuranine

CAS# 1874-54-0

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 591122
Name: Psicofuranine
CAS#: 1874-54-0
Chemical Formula: C11H5N5O5
Exact Mass: 297.11
Molecular Weight: 297.270
Elemental Analysis: C, 44.44; H, 5.09; N, 23.56; O, 26.91

Price and Availability

Size	Price	Availability
1mg	USD 315	2 weeks
5mg	USD 850	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

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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

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	50.0	168.20

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.

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

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1: McConkey GA. Plasmodium falciparum: isolation and characterisation of a gene encoding protozoan GMP synthase. Exp Parasitol. 2000 Jan;94(1):23-32. PubMed PMID: 10631077.

2: 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. PubMed PMID: 1842092.

3: 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. PubMed PMID: 2254281; PubMed Central PMCID: PMC210845.

4: 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. PubMed PMID: 2101908.

5: 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. PubMed PMID: 3907701.

6: Rosenthal A, Ratcliffe M. C4'-Branched-chain surgar nucleosides: synthesis of isomers of psicofuranine. Carbohydr Res. 1977 Mar;54(1):61-73. PubMed PMID: 861968.

7: Patel N, Moyed HS, Kane JF. Xanthosine-5'-phosphate amidotransferase from Escherichia coli. J Biol Chem. 1975 Apr 10;250(7):2609-13. PubMed PMID: 235520.

8: 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. PubMed PMID: 5332732.

9: Forist AA. Biological half-life of psicofuranine in the human. J Pharm Sci. 1965 Jun;54(6):927. PubMed PMID: 5847035.

10: SUGIMORI T, SUHADOLNIK RJ. THE BIOSYNTHESIS OF PSICOFURANINE. J Am Chem Soc. 1965 Mar 5;87:1136-7. PubMed PMID: 14284629.

11: UDAKA S, MOYED HS. INHIBITION OF PARENTAL AND MUTANT XANTHOSINE 5'-PHOSPHATE AMINASES BY PSICOFURANINE. J Biol Chem. 1963 Aug;238:2797-803. PubMed PMID: 14063305.

12: DESSI P, RIZZOLI C, CESTARI A. [ACTION OF PSICOFURANINE ON HUMAN TUMORAL ELEMENTS IN CONTINUOUS CULTURE]. Arch Ital Sci Farmacol. 1963 Apr;13:175-6. Italian. PubMed PMID: 14245136.

13: 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. PubMed PMID: 13984785.

14: COSTA G, HOLLAND JF, PICKREN JW. Acute pericarditis produced by psicofuranine, a nucleoside analogue. N Engl J Med. 1961 Dec 7;265:1143-6. PubMed PMID: 13881576.

15: MAGEE WE, EBERTS FS Jr. Studies with psicofuranine in the tumor-bearing rat. Cancer Res. 1961 Jun;21:611-9. PubMed PMID: 13765193.

16: SLECHTA L. Studies on the mode of action of psicofuranine. Biochem Pharmacol. 1960 Oct;5:96-107. PubMed PMID: 13913839.

17: 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. PubMed PMID: 13703731.

18: HANKA LJ, BURCH MR. Improved assay for psicofuranine. Antibiot Chemother (Northfield). 1960 Aug;10:484-7. PubMed PMID: 13851898.

19: HANKA LJ. Mechanism of action of psicofuranine. J Bacteriol. 1960 Jul;80:30-6. PubMed PMID: 14399485; PubMed Central PMCID: PMC278812.

20: COSTA G, HOLLAND JF. Clinical studies with psicofuranine. Cancer Chemother Rep. 1960 Jul;8:33-5. PubMed PMID: 13849455.

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