Sinefungin
featured

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

MedKoo CAT#: 561331

CAS#: 58944-73-3

Description: Sinefungin is an inhibitor of DNA methyltransferase. Sinefungin is a nucleoside related to S-adenosylmethionine and has antifungal, antiviral, and antiparasitic activities.

Chemical Structure

img
Sinefungin
CAS# 58944-73-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 561331
Name: Sinefungin
CAS#: 58944-73-3
Chemical Formula: C15H23N7O5
Exact Mass: 381.18
Molecular Weight: 381.390
Elemental Analysis: C, 47.24; H, 6.08; N, 25.71; O, 20.97

Price and Availability

Size Price Availability Quantity
1mg USD 500 2 weeks
5mg USD 700 2 weeks
10mg USD 1050 2 Weeks
25mg USD 1900 2 Weeks
Bulk inquiry

Synonym: Sinefungin; Adenosylornithine; Antibiotic A 9145;Antibiotic A 9145; Antibiotic 32232RP; RP32232; RP-32232; RP 32232;

IUPAC/Chemical Name: (2S,5S)-2,5-Diamino-6-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid

InChi Key: LMXOHSDXUQEUSF-YECHIGJVSA-N

InChi Code: InChI=1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7-,8+,10+,11+,14+/m0/s1

SMILES Code: O=C(O)[C@@H](N)CC[C@H](N)C[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O

Appearance: Solid powder

Purity: >95% (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 water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in water

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
Instruction:
View handling instruction
Biological target: Sinefungin is a potent inhibitor of virion mRNA(guanine-7-)-methyltransferase, mRNA(nucleoside-2'-)-methyltransferase, and viral multiplication. Sinefungin ameliorates renal fibrosis by inhibiting H3K4 methylation.
In vitro activity: Sinefungin can potentially offer a highly effective treatment for feline herpesvirus type 1 (FHV-1). Sinefungin inhibited in vitro growth of FHV-1 most significantly over other animal viruses, such as feline infectious peritonitis virus, equine herpesvirus, pseudorabies virus and feline calicivirus. Sinefungin specifically suppressed the replication of FHV-1 after its adsorption to the host feline kidney cells in a dose-dependent manner, without obvious cytotoxicity to the host cells. Reference: J Antibiot (Tokyo). 2019 Dec;72(12):981-985. https://pubmed.ncbi.nlm.nih.gov/31534199/
In vivo activity: S-adenosylmethionine (SAM) inhibitors, such as sinefungin could be used as lead compounds for the development of novel antibiofilm agents against pneumococci. Sinefungin significantly reduced pneumococcal colonization in rat middle ear, decreases AI-2 production, and downregulates luxS, pfs, and speE gene expressions. Reference: Biomed Res Int. 2014;2014:156987. https://pubmed.ncbi.nlm.nih.gov/25050323/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 100.0 262.20

Preparing Stock Solutions

The following data is based on the product molecular weight 381.39 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: 1. Kuroda Y, Yamagata H, Nemoto M, Inagaki K, Tamura T, Maeda K. Antiviral effect of sinefungin on in vitro growth of feline herpesvirus type 1. J Antibiot (Tokyo). 2019 Dec;72(12):981-985. doi: 10.1038/s41429-019-0234-4. Epub 2019 Sep 18. PMID: 31534199. 2. Niitsuma M, Hashida J, Iwatsuki M, Mori M, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Matsumoto A, Takahashi Y, Yamada H, Otoguro K, Shiomi K, Omura S. Sinefungin VA and dehydrosinefungin V, new antitrypanosomal antibiotics produced by Streptomyces sp. K05-0178. J Antibiot (Tokyo). 2010 Nov;63(11):673-9. doi: 10.1038/ja.2010.102. Epub 2010 Sep 22. PMID: 20859291. 3. Sasaki K, Doi S, Nakashima A, Irifuku T, Yamada K, Kokoroishi K, Ueno T, Doi T, Hida E, Arihiro K, Kohno N, Masaki T. Inhibition of SET Domain-Containing Lysine Methyltransferase 7/9 Ameliorates Renal Fibrosis. J Am Soc Nephrol. 2016 Jan;27(1):203-15. doi: 10.1681/ASN.2014090850. Epub 2015 Jun 4. PMID: 26045091; PMCID: PMC4696564. 4. Yadav MK, Park SW, Chae SW, Song JJ. Sinefungin, a natural nucleoside analogue of S-adenosylmethionine, inhibits Streptococcus pneumoniae biofilm growth. Biomed Res Int. 2014;2014:156987. doi: 10.1155/2014/156987. Epub 2014 Jun 23. PMID: 25050323; PMCID: PMC4094849.
In vitro protocol: 1. Kuroda Y, Yamagata H, Nemoto M, Inagaki K, Tamura T, Maeda K. Antiviral effect of sinefungin on in vitro growth of feline herpesvirus type 1. J Antibiot (Tokyo). 2019 Dec;72(12):981-985. doi: 10.1038/s41429-019-0234-4. Epub 2019 Sep 18. PMID: 31534199. 2. Niitsuma M, Hashida J, Iwatsuki M, Mori M, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Matsumoto A, Takahashi Y, Yamada H, Otoguro K, Shiomi K, Omura S. Sinefungin VA and dehydrosinefungin V, new antitrypanosomal antibiotics produced by Streptomyces sp. K05-0178. J Antibiot (Tokyo). 2010 Nov;63(11):673-9. doi: 10.1038/ja.2010.102. Epub 2010 Sep 22. PMID: 20859291.
In vivo protocol: 1. Sasaki K, Doi S, Nakashima A, Irifuku T, Yamada K, Kokoroishi K, Ueno T, Doi T, Hida E, Arihiro K, Kohno N, Masaki T. Inhibition of SET Domain-Containing Lysine Methyltransferase 7/9 Ameliorates Renal Fibrosis. J Am Soc Nephrol. 2016 Jan;27(1):203-15. doi: 10.1681/ASN.2014090850. Epub 2015 Jun 4. PMID: 26045091; PMCID: PMC4696564. 2. Yadav MK, Park SW, Chae SW, Song JJ. Sinefungin, a natural nucleoside analogue of S-adenosylmethionine, inhibits Streptococcus pneumoniae biofilm growth. Biomed Res Int. 2014;2014:156987. doi: 10.1155/2014/156987. Epub 2014 Jun 23. PMID: 25050323; PMCID: PMC4094849.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Meshnick SR. Recent studies on inhibitors of macromolecular synthesis and function in trypanosomes. Pharmacol Ther. 1984;25(2):239-54. Review. PubMed PMID: 6209734.