Hypothemycin

Specifications / Handling

More Information
Product Details
Product Type	Chemical
Properties
Formula	C₁₉H₂₂O₈
MW	378.4
CAS	76958-67-3
Source/Host Chemicals	Isolated from Phoma sp.
Purity Chemicals	≥98% (HPLC)
Appearance	White to off-white solid.
Solubility	Soluble in DMSO or acetone; insoluble in methanol or water.
Identity	Determined by ¹H-NMR.
Declaration	Manufactured by BioViotica.
InChi Key	SSNQAUBBJYCSMY-KNTMUCJRSA-N
Smiles	COC1=CC(O)=C2C(=C1)[C@H]1O[C@@H]1C[C@H](O)[C@H](O)C(=O)\C=C/C[C@H](C)OC2=O
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Use/Stability	Stable for at least 1 year after receipt when stored at -20°C. After reconstitution protect from light at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Antifungal.
Cytotoxic against some tumor cell lines, partly attributed to inhibition of Ras-inducible genes.
Inhibits proliferation of mouse and human T cells.
Modulates production of cytokines during T cell activation.
Facilitates the ubiquitinylation process of cyclin D1.
Potent and selective threonine/tyrosine-specific kinase, MEK and other protein kinases inhibitor in both in vitro and in vivo studies.

Product References

Metabolites of pyrenomycetes XIII: Structure of (+) hypothemycin, an antibiotic macrolide from hypomyces trichothecoides: M.S.R. Nair & S.T. Carey; Tetrahedron Lett. 21, 2011 (1980)
Metabolites of pyrenomycetes. XIV: Structure and partial stereochemistry of the antibiotic macrolides hypothemycin and dihydrohypothemycin: M.S.R. Nair, et al.; Tetrahedron 37, 2445 (1981)
Revised structure and stereochemistry of hypothemycin: T. Agatsuma et al.; Chem. Pharm. Bull. 41, 373 (1993)
Antitumor efficacy of hypothemycin, a new Ras-signaling inhibitor: H. Tanaka, et al.; Jpn. J. Cancer Res. 90, 1139 (1999)
Hypothemycin inhibits the proliferative response and modulates the production of cytokines during T cell activation: R. Camacho, et al.; Immunopharmacology 44, 255 (1999)
Resorcylic acid lactones: naturally occurring potent and selective inhibitors of MEK: A. Zhao, et al.; J. Antibiot. 52, 1086 (1999)
Suppression of oncogenic transformation by hypothemycin associated with accelerated cyclin D1 degradation through ubiquitin-proteasome pathway: H. Sonoda, et al.; Life Sci. 65, 381 (1999)
Targeted covalent inactivation of protein kinases by resorcylic acid lactone polyketides: A. Schirmer, et al.; PNAS 103, 4234 (2006)
Chemistry and biology of resorcylic acid lactones: N. Winssinger, et al.; Chem. Commun. (Camb). 1, 22 (2007), (Review)
The resorcyclic acid lactone Hypothemycin selectively inhibits the mitogen-activated protein kinase kinase-extracellular signal-regulated kinase pathway in cells: H. Fukazawa, et al.; Biol. Pharm. Bull. 33, 168 (2010)

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