YM-254890

Specifications / Handling

More Information
Product Details
Synonyms	QS 3666A
Product Type	Chemical
Properties
Formula	C₄₆H₆₉N₇O₁₅
MW	960.1
CAS	568580-02-9
Source/Host Chemicals	Isolated from Chromobacterium sp. QS3666 strain.
Purity Chemicals	≥95% (HPLC)
Appearance	Off-white solid.
Solubility	Soluble in DMSO (10mg/ml).
Identity	Determined by ¹H-NMR.
Declaration	Not sold in Japan
InChi Key	QVYLWCAYZGFGNF-WBWCVGBTSA-N
Smiles	O=C(N(C)C(C(N[C@H](C(N(C)[C@H](C(N[C@@H]([C@@H](C(C)C)OC([C@@H](NC(C)=O)[C@@H](C(C)C)O)=O)C1=O)=O)C)=O)C)=O)=C)[C@H](OC([C@@H](NC(C)=O)[C@@H](C)OC([C@@H](N1C)[C@@H](C)OC)=O)=O)CC2=CC=CC=C2
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

Cyclic depsipeptide composed of unique amino acids differing from normal amino acids.
Membrane permeable, potent and selective Gα_q family inhibitor. Acts in both in vivo and in vitro systems.
Inhibits the signal transduction of Gα_q, Gα₁₁ and Gα₁₄ (IC₅₀=0.095μM) by blocking the exchange of GDP for GTP, preventing the activation of the G protein.
Inhibits platelet aggregation induced by ADP.
Shown to inhibit Gα_q-coupled GPCR signaling by inhibiting calcium mobilization and to have antithrombotic and thrombolytic effects.
Might be used as a starting point for new approaches in cancer drug discovery.
Gα_q signaling has been shown to regulate brown/beige adipocytes using the structurally similar specific Gα_q family inhibitor FR900359. It is suggested that inhibition of this pathway may be a novel therapeutic approach to combat obesity.
The closely related compounds YM-254890 and FR900359 (UBO-QIC) are both potent and selective Gα_q family inhibitors and were for long time only restricted accessible. The commercial availability of YM-254890 might give further insights into Gα_q family signaling processes.

Product References

Structure of YM-254890, a Novel Gq/11 Inhibitor from Chromobacterium sp. QS3666: M. Taniguchi, et al.; Tetrahedron 59, 4533 (2003)
YM-254890, a novel platelet aggregation inhibitor produced by Chromobacterium sp. QS3666: M. Taniguchi, et al.; J. Antibiot. 56, 358 (2003)
A novel Galphaq/11-selective inhibitor: J. Takasaki, et al.; J. Biol. Chem. 279, 47438 (2004)
Pharmacological properties of YM-254890, a specific G(alpha)q/11 inhibitor, on thrombosis and neointima formation in mice: T. Kawasaki, et al.; Thromb. Haemost. 94, 184 (2005)
Effect of YM-254890, a specific G(alpha)q/11 inhibitor, on experimental peripheral arterial disease in rats: T. Uemura, et al.; Eur. J. Pharmacol. 536, 154 (2006)
Structural basis for the specific inhibition of heterotrimeric Gq protein by a small molecule: A. Nishimura, et al.; PNAS 107, 13666 (2010)
Structure, Function, Pharmacology, and Therapeutic Potential of the G Protein, Gα/q,11: D. Kamato, et al.; Front. Cardiovasc. Med. 2, 14 (2015) (Review)
Total synthesis of the cyclic depsipeptide YM-280193, a platelet aggregation inhibitor: H. Kaur, et al.; Org. Lett. 17, 492 (2015)
Total synthesis and structure-activity relationship studies of a series of selective G protein inhibitors: X.F. Xiong, et al.; Nat. Chem. 8, 1035 (2016)
The Gq signalling pathway inhibits brown and beige adipose tissue: K. Klepac, et al.; Nat. Commun. 7, 10895 (2016)
Gaq proteins: molecular pharmacology and therapeutic potential: D. Kamato, et al.; Cell. Mol. Life Sci. 74, 1379 (2017) (Review)
Functional characterization of uveal melanoma oncogenes: J. Ma, et al.; Oncogene, ahead of print (2020)
Exploring pharmacological inhibition of G q/11 as an analgesic strategy: S. Marwari, et al.; Br. J. Pharmacol. ahead of print (2022)

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