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Decoyinine

Names

[ CAS No. ]:
2004-04-8

[ Name ]:
Decoyinine

[Synonym ]:
6-Amino-9H-purin-9-yl 5-deoxy-β-D-erythro-pent-4-enofuranoside
decoyinine
Decoyinin
Antibiotic A 14
U-7984
β-D-erythro-Pent-4-enofuranoside, 6-amino-9H-purin-9-yl 5-deoxy-
Angustmycin A
A 14

Biological Activity

[Description]:

Decoyinine is a selective inhibitor of GMP synthetase (GMPS).

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Cancer

[Target]

GMPS[1].


[In Vitro]

Decoyinine is an analog of adenosine which causes a decrease in intracellular GTP levels by inhibition of GMP synthetase. Decoyinine exerts a stimulatory effect on oaamylase synthesis only in the strain in which the catabolite repression component of a-amylase regulation has been rendered inoperable by the gra-10 mutation. The apparent stimnulation of a-amylase activity in WLN-11 by Decoyinine is not an artifactual effect exerted at the level of enzyme activity itself. It is observed that purine nucleotides, most notably GMP, exhibits a dramatic inhibitory effect on the activity of Bacillus circulans F-2 amylase and a less-pronounced inhibitory effect on B. subtilis aamylase. At the concentration used in the experiments (1.07 mM), Decoyinine has no effect in vitro on B. subtilis WLN-11 oaamylase activity. At the same concentration, GMP exerts a slight inhibitory effect on aamylase activity[2].

[In Vivo]

It is showed that Decoyinine (Angustmycin A) treatment hinders tumor growth in xenograft mouse model. Moreover, like GMPS activity, the effect of Decoyinine does not appear to be subtype specific as it impairs growth of xenografts from cells harboring NRASQ61R (SK-Mel-103) or BRAFV600E (SK-Mel-28) mutations[1].

[Cell Assay]

The isogenic strains WLN-4 (sacA321 amyRJ-amyE+) and WLN-11 (sacA321 gra-10-amyE+) are inoculated into minimal S7 medium, containing 2% (wt/vol) glucose, from washed exponential-phase seed cultures grown in the same medium. At mid-logarithmic growth phase, each culture is evenly subdivided into two flasks containing either 1/10 the culture volume of fresh S7 medium or a 1/10 volume of filter-sterilized S7 medium to which 2.5 mg of Decoyinine per ml has previously been dissolved (final Decoyinine concentration, 250 μg/mL). At regular intervals before and after the decoyinine addition, samples are removed from the cultures and the culture supernatants are assayed for a-amylase as described previously. At 16 h after the Decoyinine addition, the frequency of heatresistant spores in each culture is determined[2].

[Animal admin]

Mice[1] SK-Mel-103 and SK-Mel-28 cells are inoculated subcutaneously in both flanks of SCID mice (18 mice/cell line). Once tumors volume reach approximately 100 mm3, mice are randomly assigned to one of four groups and treated with daily i.p. injections of Decoyinine (120 mg/kg), MMF (30 mg/kg), or with respective vehicles. Tumor size is measured every other day with a caliper and mice are killed once tumor volume reach 1000 mm3 or the animals show signs of morbidity[1].

[References]

[1]. A Bianchi-Smiraglia, et al. Pharmacological targeting of guanosine monophosphate synthase suppresses melanoma cell invasion and tumorigenicity. Cell Death Differ. 2015 Nov; 22(11): 1858–1864.

[2]. W L Nicholson, et al. Effect of Decoyinine on the regulation of alpha-amylase synthesis in Bacillus subtilis. J Bacteriol. 1987 Dec; 169(12): 5867–5869.


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Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
580.3±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C11H13N5O4

[ Molecular Weight ]:
279.25

[ Flash Point ]:
304.7±32.9 °C

[ PSA ]:
128.54000

[ LogP ]:
-1.25

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.837

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AU6256000
CHEMICAL NAME :
Adenine, 9-(6-deoxy-beta-D-erythro-hex-5-enulofuranosyl)-
CAS REGISTRY NUMBER :
2004-04-8
LAST UPDATED :
199106
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C11-H13-N5-O4
MOLECULAR WEIGHT :
279.29

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>2500 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 :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1 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
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 5,294,1981

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ RIDADR ]:
NONH for all modes of transport

Articles

Metabolic initiation of differentiation and secondary metabolism by Streptomyces griseus: significance of the stringent response (ppGpp) and GTP content in relation to A factor.

J. Bacteriol. 169(8) , 3608-16, (1987)

I investigated the significance of the intracellular accumulation of guanosine 5'-diphosphate 3'-diphosphate (ppGpp) and of the coordinated decrease in the GTP pool for initiating morphological and ph...

DegS-DegU and ComP-ComA modulator-effector pairs control expression of the Bacillus subtilis pleiotropic regulatory gene degQ.

J. Bacteriol. 173(7) , 2366-77, (1991)

Production of a class of both secreted and intracellular degradative enzymes in Bacillus subtilis is regulated at the transcriptional level by a signal transduction pathway which includes the DegS-Deg...

Multiple regulatory sites in the Bacillus subtilis citB promoter region.

J. Bacteriol. 172(9) , 5408-15, (1990)

The aconitase (citB) gene of Bacillus subtilis is repressed during growth in a medium that contains a rapidly metabolizable carbon source and a source of 2-ketoglutarate. It is derepressed when either...


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