AdipoGen Life Sciences

Siamycin I

CHF 110.00
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AG-CN2-0146-C250250 µgCHF 110.00
AG-CN2-0146-M0011 mgCHF 330.00
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Product Details
Synonyms MS-271; FR 901724; BMY 29304
Product Type Chemical
Properties
Formula

C97H131N23O26S4

MW 2163.5
Sequence

CLGVGSCNDFAGCGYAIVCFW

CAS 164802-68-0
Source/Host Chemicals Isolated from Streptomyces sp.
Purity Chemicals ≥85% (HPLC) (Mixture containing ≤15% Siamycin II)
Appearance White solid.
Solubility Soluble in DMSO or methanol.
InChi Key TXYRKTDGDMHVHR-NEKRQKPVSA-N
Smiles [H]OC(=O)[C@@]([H])(N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@@]1([H])N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@@]([H])(N([H])C(=O)C([H])([H])N([H])C(=O)[C@@]2([H])N([H])C(=O)C([H])([H])N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@@]3([H])N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@@]([H])(N([H])C(=O)C([H])([H])N([H])C(=O)[C@@]([H])(N([H])C(=O)C([H])([H])N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@@]([H])(N([H])C(=O)C3([H])[H])C([H])([H])SSC2([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])O[H])C([H])([H])SSC1([H])[H])C([H])([H])C(=O)N([H])[H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])[H])C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Antibiotic [1].
  • Lariat peptide antiviral [1].
  • Anti-HIV and anti-HSV (Herpes simplex virus) agent [4-6].
  • Fsr quorum sensing inhibitor [7-9].
  • Calmodulin-activated myosin light chain kinase (MLCK) inhibitor [2, 3].
Product References
  1. Siamycins I and II, new anti-HIV peptides: I. Fermentation, isolation, biological activity and initial characterization: M. Tsunakawa, et al.; J. Antibiot. 48, 433 (1995)
  2. MS-271, a novel inhibitor of calmodulin-activated myosin light chain kinase from Streptomyces sp.--I. Isolation, structural determination and biological properties of MS-271: K. Yano, et al.; Bioorg. Med. Chem. 4, 115 (1996)
  3. MS-271, A Novel Inhibitor of Calmodulin-Activated Myosin Light Chain Kinase from Streptomyces sp.--II. Solution Structure of MS-271: Characteristic Features of the 'Lasso' Structure: R. Katahira, et al.; Bioorg. & Med. Chem. 4, 121 (1996)
  4. FR901724, a novel anti-human immunodeficiency virus (HIV) peptide produced by Streptomyces, shows synergistic antiviral activities with HIV protease inhibitor and 2',3'-dideoxynucleosides: H. Nakashima, et al.; Biol. Pharm. Bull. 19, 405 (1996)
  5. Characterization of siamycin I, a human immunodeficiency virus fusion inhibitor: P.F. Lin, et al.; Antimicrob. Agents Chemother. 40, 133 (1996)
  6. Current Lead Natural Products for the Chemotherapy of Human Immunodeficiency Virus (HIV) Infection: E. De Clercq; Med. Res. Rev. 20, 323 (2000)
  7. Siamycin Attenuates fsr Quorum Sensing Mediated by a Gelatinase Biosynthesis-Activating Pheromone in Enterococcus faecalis: J. Nakayama, et al.; J. Bacteriol. 189, 1358 (2007)
  8. Two-component signal transduction as potential drug targets in pathogenic bacteria: Y. Gotoh, et al.; Curr. Opin. Microbiol. 13, 232 (2010)
  9. Anti-HIV siamycin I directly inhibits autophosphorylation activity of the bacterial FsrC quorum sensor and other ATP-dependent enzyme activities: P. Ma, et al.; FEBS Lett. 585, 2660 (2011)
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