2004-04-8
2004-04-8 structure
- Name: Decoyinine
- Chemical Name: (2R,3R,4S)-2-(6-aminopurin-9-yl)-2-(hydroxymethyl)-5-methylideneoxolane-3,4-diol
- CAS Number: 2004-04-8
- Molecular Formula: C11H13N5O4
- Molecular Weight: 279.25
- Catalog: Research Areas Cancer
- Create Date: 2018-09-22 12:51:21
- Modify Date: 2024-01-11 17:06:48
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Decoyinine is a selective inhibitor of GMP synthetase (GMPS).
| Name | (2R,3R,4S)-2-(6-aminopurin-9-yl)-2-(hydroxymethyl)-5-methylideneoxolane-3,4-diol |
|---|---|
| Synonyms |
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 |
| Description | Decoyinine is a selective inhibitor of GMP synthetase (GMPS). |
|---|---|
| Related Catalog | |
| 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 |
| 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℃ |
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
|
| Symbol |
GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H315-H319-H335 |
| Precautionary Statements | P261-P305 + P351 + P338 |
| RIDADR | NONH for all modes of transport |