Sparsomycin

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

MedKoo CAT#: 584391

CAS#: 1404-64-4

Description: Sparsomycin is an antitumor antibiotic produced by Streptomyces sparsogenes. It inhibits protein synthesis in 70S and 80S ribosomal systems.

Chemical Structure

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Sparsomycin
CAS# 1404-64-4
Instruction

Theoretical Analysis

MedKoo Cat#: 584391
Name: Sparsomycin
CAS#: 1404-64-4
Chemical Formula: C13H19N3O5S2
Exact Mass: 361.08
Molecular Weight: 361.431
Elemental Analysis: C, 43.20; H, 5.30; N, 11.63; O, 22.13; S, 17.74

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Sparsomycin; U 19183; U-19183; U19183; B 120121L19; B120121L19; Esparsomicina

IUPAC/Chemical Name: 2-Propenamide, N-(1-(hydroxymethyl)-2-(((methylthio)methyl)sulfinyl)ethyl)-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinyl)-, (S-(E))-

InChi Key: XKLZIVIOZDNKEQ-RVUDUMFNSA-N

InChi Code: InChI=1S/C13H19N3O5S2/c1-8-10(12(19)16-13(20)14-8)3-4-11(18)15-9(5-17)6-23(21)7-22-2/h3-4,9,17H,5-7H2,1-2H3,(H,15,18)(H2,14,16,19,20)/b4-3+/t9-,23?/m0/s1

SMILES Code: O=C(N[C@@H](CO)CS(CSC)=O)/C=C/C1=C(C)NC(NC1=O)=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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 361.43 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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

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1: Miyauchi K, Komano J, Myint L, Futahashi Y, Urano E, Matsuda Z, Chiba T, Miura H, Sugiura W, Yamamoto N. Rapid propagation of low-fitness drug-resistant mutants of human immunodeficiency virus type 1 by a streptococcal metabolite sparsomycin. Antivir Chem Chemother. 2006;17(4):167-74. PubMed PMID: 17066895.

2: Ge X, Roux B. Absolute binding free energy calculations of sparsomycin analogs to the bacterial ribosome. J Phys Chem B. 2010 Jul 29;114(29):9525-39. doi: 10.1021/jp100579y. PubMed PMID: 20608691.

3: Li S, Cheng X, Zhou Y, Xi Z. Sparsomycin-linezolid conjugates can promote ribosomal translocation. Chembiochem. 2011 Dec 16;12(18):2801-6. doi: 10.1002/cbic.201100508. Epub 2011 Oct 28. PubMed PMID: 22038852.

4: Ge X, Roux B. Calculation of the standard binding free energy of sparsomycin to the ribosomal peptidyl-transferase P-site using molecular dynamics simulations with restraining potentials. J Mol Recognit. 2010 Mar-Apr;23(2):128-41. doi: 10.1002/jmr.996. PubMed PMID: 20151411.

5: Ottenheijm HC, van den Broek LA, Ballesta JP, Zylicz Z. Chemical and biological aspects of sparsomycin, an antibiotic from Streptomyces. Prog Med Chem. 1986;23:219-68. Review. PubMed PMID: 3310108.

6: Nakajima N, Enomoto T, Matsuura N, Ubukata M. Synthesis and morphological reversion activity on srctsNRK cells of pyrimidinylpropanamide antibiotics, sparsomycin, sparoxomycin A1, A2, and their analogues. Bioorg Med Chem Lett. 1998 Dec 1;8(23):3331-4. PubMed PMID: 9873729.

7: Lazaro E, van den Broek LA, San Felix A, Ottenheijm HC, Ballesta JP. Biochemical and kinetic characteristics of the interaction of the antitumor antibiotic sparsomycin with prokaryotic and eukaryotic ribosomes. Biochemistry. 1991 Oct 8;30(40):9642-8. PubMed PMID: 1911750.

8: Kallia-Raftopoulos S, Synetos D, Ottenheijm HC, van den Broek LA, Coutsogeorgopoulos C. Sparsomycin and its analogues: a new approach for evaluating their potency as inhibitors of peptide bond formation. Mol Pharmacol. 1996 Jun;49(6):1085-91. PubMed PMID: 8649347.

9: Ermolenko DN, Cornish PV, Ha T, Noller HF. Antibiotics that bind to the A site of the large ribosomal subunit can induce mRNA translocation. RNA. 2013 Feb;19(2):158-66. doi: 10.1261/rna.035964.112. Epub 2012 Dec 17. PubMed PMID: 23249745; PubMed Central PMCID: PMC3543091.

10: Lazaro E, San Felix A, van den Broek LA, Ottenheijm HC, Ballesta JP. Interaction of the antibiotic sparsomycin with the ribosome. Antimicrob Agents Chemother. 1991 Jan;35(1):10-3. PubMed PMID: 2014963; PubMed Central PMCID: PMC244933.

11: Hofs HP, Wagener DJ, De Vos D, Ottenheijm HC, Winkens HJ, Bovee PH, De Grip WJ. Antitumour activity and retinotoxicity of ethyldeshydroxy-sparsomycin in mice. Eur J Cancer. 1995;31A(9):1526-30. PubMed PMID: 7577083.

12: Tan GT, DeBlasio A, Mankin AS. Mutations in the peptidyl transferase center of 23 S rRNA reveal the site of action of sparsomycin, a universal inhibitor of translation. J Mol Biol. 1996 Aug 16;261(2):222-30. PubMed PMID: 8757289.

13: van den Broek LA, Liskamp RM, Colstee JH, Lelieveld P, Remacha M, Vázquez D, Ballesta JP, Ottenheijm HC. Structure-activity relationships of sparsomycin and its analogues. Inhibition of peptide bond formation in cell-free systems and of L1210 and bacterial cell growth. J Med Chem. 1987 Feb;30(2):325-33. PubMed PMID: 3543365.

14: Hofs HP, Wagener DJ, De Valk-Bakker V, Van Rennes H, Van Zeist AJ, Van Den Broek LA, Ottenheijm HC. Potentiation of cisplatin antitumour activity by Ethyldeshydroxy-Sparsomycin in L1210 leukemia. Anticancer Res. 1992 Jan-Feb;12(1):167-70. PubMed PMID: 1567164.

15: Hofs HP, Wagener TD, de Valk-Bakker V, van Rennes H, Doesburg WH, Ottenheijm HC, de Grip WJ. The effect of ethyldeshydroxy-sparsomycin and cisplatin on the intracellular glutathione level and glutathione S-transferase activity. Anticancer Drugs. 1997 Apr;8(4):349-57. PubMed PMID: 9180388.

16: Parry RJ, Hoyt JC. Purification and preliminary characterization of (E)-3-(2,4-dioxo-6-methyl-5-pyrimidinyl)acrylic acid synthase, an enzyme involved in biosynthesis of the antitumor agent sparsomycin. J Bacteriol. 1997 Feb;179(4):1385-92. PubMed PMID: 9023226; PubMed Central PMCID: PMC178840.

17: Lázaro E, Sanz E, Remacha M, Ballesta JP. Characterization of sparsomycin resistance in Streptomyces sparsogenes. Antimicrob Agents Chemother. 2002 Sep;46(9):2914-9. PubMed PMID: 12183247; PubMed Central PMCID: PMC127450.

18: Poehland BL, Chan JA. Direct broth assay for sparsomycin and related nucleoside antitumor antibiotics using reversed-phase high-performance liquid chromatography. J Chromatogr. 1988 May 20;439(2):459-65. PubMed PMID: 3403654.

19: Kanatomo S, Wada A, Hamaoka Y, Nagai S, Fukuda S, Tanaka M, Sasaki T. Sparsomycin analogs. V. Synthesis and antitumor activity of (E)-beta-(pyrimidin-5-yl)acrylamides. Chem Pharm Bull (Tokyo). 1988 Nov;36(11):4421-5. PubMed PMID: 3246010.

20: Zylicz Z, Wagener DJ, Garzotto M, Vree TB, van der Kleijn E, van den Broek LA, Ottenheijm HC. Preclinical pharmacokinetics of the antitumor antibiotic deshydroxy-sparsomycin in beagle dogs. Anticancer Res. 1988 Nov-Dec;8(6):1381-5. PubMed PMID: 3218972.