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(Synonyms: 肾上腺酮盐酸盐) 目录号 : GC13814

Decoyinine (Angustmycin A), a specific inhibitor of bacterial GMPS, has been isolated from Streptomyces .

Adrenalone HCl Chemical Structure

Cas No.:62-13-5

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Sample solution is provided at 25 µL, 10mM.

Description

Decoyinine (Angustmycin A), a specific inhibitor of bacterial GMPS, has been isolated from Streptomyces hygroscopius as a potential antibiotic with sporulation-inducing activity in Bacillus subtilis[1-3]. Angustmycin A was also recently found to be a promising cytokinin that induces adventitious root or bud differentiation[5].

With 2 mM of Angustmycin A treatment of SK-Mel-28 and SK-Mel103 cells reduced their invasion by ~30% compared with vehicle-treated cells[4]. Decoyinine (Angustmycin A) (>1mM) enabled the S. griseus IFO 13189 cells to develop aerial mycelia in the suppressed cultures at concentrations which only partially inhibited growth[6].

Decoyinine (Angustmycin A)(120 mg/kg; i.p., 10days) treatment resulted in a 36% reduction of xenografts volume while MMF caused only 19% volume reduction in SK-Mel-103 mcie. In SK-Mel-28 mcie, the xenograft volume reduction caused by angustmycin A(120 mg/kg; i.p., 27days) and MMF were of 62% and 30%, respectively[4].

References:
[1]. Vasantha N, Freese E. Enzyme changes during Bacillus subtilis sporulation caused by deprivation of guanine nucleotides. J Bacteriol. 1980 Dec;144(3):1119-25. doi: 10.1128/jb.144.3.1119-1125.1980. PMID: 6777366; PMCID: PMC294778.
[2]. Ikehara K, Okamoto M, et,al. Induction of Bacillus subtilis sporulation by decoyinine and the concomitant disappearance of ppGpp in vegetative cells. J Biochem 1982; 91: 1089-1092.
[3]. Mitani T, Heinze JE, et,al. Induction of sporulation in Bacillus subtilis by decoyinine or hadacidin. Biochem Biophys Res Commun 1977; 77: 1118-1125.
[4]. Bianchi-Smiraglia A, Wawrzyniak JA, et,al.Pharmacological targeting of guanosine monophosphate synthase suppresses melanoma cell invasion and tumorigenicity. Cell Death Differ. 2015 Nov;22(11):1858-64. doi: 10.1038/cdd.2015.47. Epub 2015 Apr 24. PMID: 25909885; PMCID: PMC4648332.
[5]. Hong-Yuan, X., Hong-Zhang, X., et,al. in Biotechnology and Sustainable Agriculture 2006 and Beyond (eds. Xu, Z., Li, J., Xue, Y. & Yang, W.) 97-101 (Springer Netherlands, 2010).
[6]. Ochi K. 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. 1987 Aug;169(8):3608-16. doi: 10.1128/jb.169.8.3608-3616.1987. PMID: 3112126; PMCID: PMC212439.

实验参考方法

Cell experiment [1]:

Cell lines

SK-Mel-28 and SK-Mel103 cells

Preparation Method

Cells were incubated with 2 mM Decoyinine (Angustmycin A) for 24h before invasion assay. Where indicated, cells were supplemented with 100 µM guanosine. Control cells were treated with equal volumes of DMSO. Drug treatments were maintained throughout the experimental procedure.

Reaction Conditions

2 mM;24h

Applications

Treatment of SK-Mel-28 and SK-Mel103 cells with 2 mM of Decoyinine(Angustmycin A) reduced their invasion by ~30% compared with vehicle-treated cells.

Animal experiment [2]:

Animal models

4-6-week-old female SCID mice

Preparation Method

SK-Mel-103 and SK-Mel-28 cells were inoculated into both flanks of SCID mice. When tumors reached 100 mm3 in size, mice were randomly assigned to different treatment groups and treated with daily i.p. injection of Decoyinine (Angustmycin A) (120 mg/kg in 10% DMSO in PBS), Mycophenolate Mofetil, or the correspondent vehicle control.

Dosage form

120 mg/kg; i.p., 10-27days

Applications

In SK-Mel-103 cells mcie, Decoyinine (Angustmycin A) treatment resulted in a 36% reduction of xenografts volume while MMF caused only 19% volume reduction. In SK-Mel-28 cells mcie, the xenograft volume reduction caused by Decoyinine (Angustmycin A) and MMF were of 62% and 30%, respectively.

References:

[1]. Bianchi-Smiraglia A, Wawrzyniak JA, et,al.Pharmacological targeting of guanosine monophosphate synthase suppresses melanoma cell invasion and tumorigenicity. Cell Death Differ. 2015 Nov;22(11):1858-64. doi: 10.1038/cdd.2015.47. Epub 2015 Apr 24. PMID: 25909885; PMCID: PMC4648332.

化学性质

Cas No. 62-13-5 SDF
别名 肾上腺酮盐酸盐
化学名 1-(3,4-dihydroxyphenyl)-2-(methylamino)ethanone;hydrochloride
Canonical SMILES CNCC(=O)C1=CC(=C(C=C1)O)O.Cl
分子式 C9H11NO3.HCl 分子量 217.65
溶解度 ≥ 10.88mg/mL in DMSO 储存条件 Store at -20°C,unstable in solution, ready to use.
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1 mM 4.5945 mL 22.9727 mL 45.9453 mL
5 mM 0.9189 mL 4.5945 mL 9.1891 mL
10 mM 0.4595 mL 2.2973 mL 4.5945 mL
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