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

Product-specific References

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

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)
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)
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)
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)
Characterization of siamycin I, a human immunodeficiency virus fusion inhibitor: P.F. Lin, et al.; Antimicrob. Agents Chemother. 40, 133 (1996)
Current Lead Natural Products for the Chemotherapy of Human Immunodeficiency Virus (HIV) Infection: E. De Clercq; Med. Res. Rev. 20, 323 (2000)
Siamycin Attenuates fsr Quorum Sensing Mediated by a Gelatinase Biosynthesis-Activating Pheromone in Enterococcus faecalis: J. Nakayama, et al.; J. Bacteriol. 189, 1358 (2007)
Two-component signal transduction as potential drug targets in pathogenic bacteria: Y. Gotoh, et al.; Curr. Opin. Microbiol. 13, 232 (2010)
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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