Psicofuranine

Names

[ Name ]:
Psicofuranine

[Synonym ]:
Adenine,9beta-D-psicofuranosyl
6-Amino-9-D-psicofuranosylpurine
Psicofuranosyladenine
Angustmycin C
psicofuranine
angustmicine C

Biological Activity

[Description]:

Psicofuramine a nucleoside antibiotic and has the inhibition of xanthosine 5'-phosphate aminase. Psicofuranine also specifically inhibits GMP synthase, and interrupts parasite growth. Psicofuranine exhibits a dose-dependent inhibition of P. falciparum growth[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Xanthosine 5'-phosphate aminase[2] P. falciparum[1] E. coli[1]

[In Vitro]

Psicofuranine specifically inhibits bacterial GMP synthase as demonstrated by isolation of Psicofuranine-resistant Escherichia coli mutants with mutations in the gene encoding GMP synthase and inhibition of bacterial growth. Psicofuranine exhibits a dose-dependent inhibition of P. falciparum growth with an IC50 of 0.3 mM. The Psicofuranine inhibitory concentration is similar to that of E. coli[1].

[References]

[1]. cConkey GA. Plasmodium falciparum: isolation and characterisation of a gene encoding protozoan GMP synthase. Exp Parasitol. 2000 Jan;94(1):23-32.

[2]. UDAKA S, et al. INHIBITION OF PARENTAL AND MUTANT XANTHOSINE 5'-PHOSPHATE AMINASES BY PSICOFURANINE. J Biol Chem. 1963 Aug;238:2797-803.

Chemical & Physical Properties

[ Density]:
2.02g/cm3

[ Boiling Point ]:
720.1ºC at 760 mmHg

[ Molecular Formula ]:
C₁₁H₁₅N₅O₅

[ Molecular Weight ]:
297.26700

[ Flash Point ]:
389.3ºC

[ Exact Mass ]:
297.10700

[ PSA ]:
159.77000

[ Vapour Pressure ]:
9.24E-22mmHg at 25°C

[ Index of Refraction ]:
1.855

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AU7100000

CHEMICAL NAME :: Adenine, 9-beta-D-psicofuranosyl-

CAS REGISTRY NUMBER :: 1874-54-0

BEILSTEIN REFERENCE NO. :: 0095142

LAST UPDATED :: 199612

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C11-H15-N5-O5

MOLECULAR WEIGHT :: 297.31

WISWESSER LINE NOTATION :: T56 BN DN FN HNJ IZ D- BT5OTJ B1Q CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 gm/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

REFERENCE :: ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 9,675,1959

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 13 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,842,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1695 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: UPJOH* "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." (Kalamazoo, MI 49001) Volume(issue)/page/year: 2(6),-,1971

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,842,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: UPJOH* "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." (Kalamazoo, MI 49001) Volume(issue)/page/year: 2(6),-,1971 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 9800 mg/kg/28D-I

TOXIC EFFECTS :: Liver - other changes Blood - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 9,675,1959 *** REVIEWS *** TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 2,159,1973

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Related Compounds

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