Angustmycin A | CAS# 2004-04-8 | Antibiotic

MedKoo Cat#: 571027 | Name: Angustmycin A

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Angustmycin A is a nucleoside-analog inhibitor of GMPS (guanosine monophosphate synthase) produced by Streptomyces hygroscopius that efficiently suppresses melanoma cell invasion in vitro and tumorigenicity in immunocompromised mice. Angustmycin A may be used as an anti-melanoma agent when considering GMPS as a driver of melanoma.

Chemical Structure

Angustmycin A

CAS#2004-04-8

Theoretical Analysis

MedKoo Cat#: 571027

Name: Angustmycin A

CAS#: 2004-04-8

Chemical Formula: C11H13N5O4

Exact Mass: 279.0968

Molecular Weight: 279.26

Elemental Analysis: C, 47.31; H, 4.69; N, 25.08; O, 22.92

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 90.00	Ready to ship
5mg	USD 350.00	Ready to ship

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Synonym

Angustmycin A; Antibiotic A 14; Decoyinine; Decoyinin; 5,6-Psicofuranosenyladenine;

IUPAC/Chemical Name

(2R,3R,4S)-2-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-5-methylenetetrahydrofuran-3,4-diol

InChi Key

UZSSGAOAYPICBZ-SOCHQFKDSA-N

InChi Code

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

SMILES Code

OC[C@](OC1=C)(N2C(N=CN=C3N)=C3N=C2)[C@@H]([C@@H]1O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C9R11B13

QC Data

View QC data: current batch, Lot#C9R11B13

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

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

In vitro activity:

Whether GMPS inhibition via angustmycin A may inhibit melanoma cells invasion was investigated. Treatment of SK-Mel-28 and SK-Mel103 cells with 2 mM of Angustmycin A (maximum concentration not affecting proliferation of studied cells) reduced their invasion by ~30% compared with vehicle-treated cells (Figure 4a), mirroring the phenotype caused by GMPS depletion (Figure 1b). Furthermore, as observed with GMPS depletion, supplementation with 100 μM of guanosine negated the effect of angustmycin A (Figure 4a). Thus, pharmacological inhibition of GMPS phenocopies the effects of GMPS genetic inhibition on melanoma cells invasive ability and its guanosine dependence. Reference: Cell Death Differ. 2015 Nov;22(11):1858-64. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648332/

In vivo activity:

The anti-melanoma efficacy of angustmycin A was investigated in a preclinical mouse model. SK-Mel-103 and SK-Mel-28 cells were inoculated subcutaneously in both flanks of SCID mice (18 mice/cell line). Once tumors volume reached approximately 100 mm3, mice were randomly assigned to a group and treated with daily i.p. injections of angustmycin A (120 mg/kg) or vehicle. In SK-Mel-103 cells, angustmycin A treatment resulted in a 36% reduction of xenografts volume compared with vehicle, (Figure 4b). In SK-Mel-28 cells, the xenograft volume reduction caused by angustmycin A was of 62% (Figure 4b). Reference: Cell Death Differ. 2015 Nov;22(11):1858-64. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648332/

Preparing Stock Solutions

The following data is based on the product molecular weight 279.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Bianchi-Smiraglia A, Wawrzyniak JA, Bagati A, Marvin EK, Ackroyd J, Moparthy S, Bshara W, Fink EE, Foley CE, Morozevich GE, Berman AE, Shewach DS, Nikiforov MA. 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.

In vitro protocol:

In vivo protocol:

1: Yu L, Zhou W, She Y, Ma H, Cai YS, Jiang M, Deng Z, Price NPJ, Chen W. Efficient biosynthesis of nucleoside cytokinin angustmycin A containing an unusual sugar system. Nat Commun. 2021 Nov 17;12(1):6633. doi: 10.1038/s41467-021-26928-y. PMID: 34789759; PMCID: PMC8599513. 2: Prisbe EJ, Smejkal J, Verheyden JP, Moffatt JG. Halo sugar nucleosides. 5. Synthesis of angustmycin A and some base analogues. J Org Chem. 1976 May 14;41(10):1836-46. doi: 10.1021/jo00872a034. PMID: 1262989. 3: Bianchi-Smiraglia A, Wawrzyniak JA, Bagati A, Marvin EK, Ackroyd J, Moparthy S, Bshara W, Fink EE, Foley CE, Morozevich GE, Berman AE, Shewach DS, Nikiforov MA. 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. 4: McCarthy JR Jr, Robins RK, Robins MJ. Purine nucleosides. XXII. The synthesis of angustmycin A (decoyinine) and related unsaturated nucleosides. J Am Chem Soc. 1968 Aug 28;90(18):4993-9. doi: 10.1021/ja01020a038. PMID: 5665542. 5: YUNTSEN H. On the studies of angustmycins. VI. Chemical structure of angustmycin A. J Antibiot (Tokyo). 1958 Mar;11(2):79-80. PMID: 13549347. 6: Someya A, Tanaka N. Interaction of aminoglycosides and other antibiotics with actin. J Antibiot (Tokyo). 1979 Feb;32(2):156-60. doi: 10.7164/antibiotics.32.156. PMID: 155669. 7: Slack FJ, Mueller JP, Strauch MA, Mathiopoulos C, Sonenshein AL. Transcriptional regulation of a Bacillus subtilis dipeptide transport operon. Mol Microbiol. 1991 Aug;5(8):1915-25. doi: 10.1111/j.1365-2958.1991.tb00815.x. PMID: 1766371. 8: Hasan A, Srivastava PC. Synthesis and biological studies of unsaturated acyclonucleoside analogues of S-adenosyl-L-homocysteine hydrolase inhibitors. J Med Chem. 1992 Apr 17;35(8):1435-9. doi: 10.1021/jm00086a012. PMID: 1573637. 9: Ochi K, Freese E. A decrease in S-adenosylmethionine synthetase activity increases the probability of spontaneous sporulation. J Bacteriol. 1982 Oct;152(1):400-10. doi: 10.1128/jb.152.1.400-410.1982. PMID: 6811558; PMCID: PMC221429. 10: 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. 11: Ochi K. A decrease in GTP content is associated with aerial mycelium formation in Streptomyces MA406-A-1. J Gen Microbiol. 1986 Feb;132(2):299-305. doi: 10.1099/00221287-132-2-299. PMID: 3711859. 12: Fouet A, Sonenshein AL. A target for carbon source-dependent negative regulation of the citB promoter of Bacillus subtilis. J Bacteriol. 1990 Feb;172(2):835-44. doi: 10.1128/jb.172.2.835-844.1990. PMID: 2105305; PMCID: PMC208513. 13: Saito N, Matsubara K, Watanabe M, Kato F, Ochi K. Genetic and biochemical characterization of EshA, a protein that forms large multimers and affects developmental processes in Streptomyces griseus. J Biol Chem. 2003 Feb 21;278(8):5902-11. doi: 10.1074/jbc.M208564200. Epub 2002 Dec 17. PMID: 12488450. 14: Andreis PG, Tortorella C, Malendowicz LK, Rebuffat P, Mazzocchi G, Neri G, Nussdorfer GG. Guanylin: a novel regulatory peptide possibly involved in the control of Ca2+-dependent agonist-stimulated aldosterone secretion in rats. Int J Mol Med. 1999 Jan;3(1):59-62. doi: 10.3892/ijmm.3.1.59. PMID: 9864386. 15: Mueller JP, Mathiopoulos C, Slack FJ, Sonenshein AL. Identification of Bacillus subtilis adaptive response genes by subtractive differential hybridization. Res Microbiol. 1991 Sep-Oct;142(7-8):805-13. doi: 10.1016/0923-2508(91)90059-j. PMID: 1784820. 16: Xu H, Meng A, Li C, Deng X, Yang M, Zhou Q, Huang C, Xu H. [Effects of angustmycin on callus occurrence and proliferation of Panax notogingseng in vitro]. Zhong Yao Cai. 2004 Jan;27(1):1-3. Chinese. PMID: 15179778. 17: Healy J, Weir J, Smith I, Losick R. Post-transcriptional control of a sporulation regulatory gene encoding transcription factor sigma H in Bacillus subtilis. Mol Microbiol. 1991 Feb;5(2):477-87. doi: 10.1111/j.1365-2958.1991.tb02131.x. PMID: 1904128. 18: Dingman DW, Rosenkrantz MS, Sonenshein AL. Relationship between aconitase gene expression and sporulation in Bacillus subtilis. J Bacteriol. 1987 Jul;169(7):3068-75. doi: 10.1128/jb.169.7.3068-3075.1987. PMID: 3110134; PMCID: PMC212350. 19: Fouet A, Jin SF, Raffel G, Sonenshein AL. Multiple regulatory sites in the Bacillus subtilis citB promoter region. J Bacteriol. 1990 Sep;172(9):5408-15. doi: 10.1128/jb.172.9.5408-5415.1990. PMID: 2118511; PMCID: PMC213206. 20: Parmagnani AS, Mannino G, Brillada C, Novero M, Dall'Osto L, Maffei ME. Biology of Two-Spotted Spider Mite (Tetranychus urticae): Ultrastructure, Photosynthesis, Guanine Transcriptomics, Carotenoids and Chlorophylls Metabolism, and Decoyinine as a Potential Acaricide. Int J Mol Sci. 2023 Jan 15;24(2):1715. doi: 10.3390/ijms24021715. PMID: 36675229; PMCID: PMC9864819.