CAS Number2004-04-8
Synonyms6-Amino-9H-purin-9-yl 5-deoxy-β-D-erythro-pent-4-enofuranoside; decoyinine; Decoyinin; Antibiotic A 14; U-7984; Angustmycin A; A 14
Molecular FormulaC11H13O4N5
Molecular Weight279.26
Purity95%
Density1.9±0.1 g/cm3
Boiling Point580.3±60.0 °C at 760 mmHg
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 2004-04-8 |
| Catalog No. | 2A-9093758 |
| Chinese Name | 德夸菌素 |
| Synonyms | 6-Amino-9H-purin-9-yl 5-deoxy-β-D-erythro-pent-4-enofuranoside; decoyinine; Decoyinin; Antibiotic A 14; U-7984; Angustmycin A; A 14 |
| Molecular Formula | C11H13O4N5 |
| Molecular Weight | 279.26 |
| Purity | 95 |
| Density | 1.9±0.1 g/cm3 |
| Boiling Point | 580.3±60.0 °C at 760 mmHg |
| Storage Condition | 2-8℃ |
| Application | Decoyinine is a selective inhibitor of GMP synthase. |
| PubChem ID | 804395 |
| MDL Number | MFCD31689304 |
| SMILES | C=C1OC(CO)(n2cnc3c(N)ncnc32)C(O)C1O |
| InChI | InChI=1S/C11H13N5O4/c1-5-7(18)8(19)11(2-17,20-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-4,7-8,17-19H,1-2H2,(H2,12,13,14)/t7-,8-,11-/m1/s1 |
| InChI Key | UZSSGAOAYPICBZ-SOCHQFKDSA-N |
| Hazard Symbols | transportation |
| MSDS | msds/93758_1_2004_04_8.pdf |
| Bioactivity | 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. 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 InChIKey UZSSGAOAYPICBZ-SOCHQFKDSA-N SMILES C=C1OC(CO)(n2cnc3c(N)ncnc32)C(O)C1O Storage condition 2-8℃ |
| Use of | Decoyinine is a selective inhibitor of GMP synthetase (GMPS). Properties Articles28 Name (2R,3R,4S)-2-(6-aminopurin-9-yl)-2-(hydroxymethyl)-5-methylideneoxolane-3,4-diol Synonym More Synonyms Decoyinine Biological Activity Description Decoyinine is a selective inhibitor of GMP synthetase (GMPS). Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Cancer 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]. 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. Chemical & Physical Properties Molecular Formula C11H13N5O4 PSA 128.54000 LogP -1.25 Index of Refraction 1.837 InChIKey UZSSGAOAYPICBZ-SOCHQFKDSA-N Storage condition 2-8℃ |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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