YM-254890

Product Code: AG-CN2-0509

Product Group: Natural Products and Extracts

Code	Size	Price

AG-CN2-0509-MC05

500 ug

£200.00

Quantity:

AG-CN2-0509-M001

1 mg

£330.00

Quantity:

Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO

Shipping:

Ambient

Storage:

-20°C

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1 / 1

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Documents

Further Information

Alternate Names/Synonyms:

QS 3666A

Appearance:

Off-white solid.

CAS:

568580-02-9

EClass:

32160000

Form (Short):

liquid

Handling Advice:

Keep cool and dry.

InChi:

InChI=1S/C46H69N7O15/c1-22(2)37(56)34(49-30(11)55)45(63)68-38(23(3)4)35-43(61)53(14)36(28(9)65-15)46(64)66-27(8)33(48-29(10)54)44(62)67-32(21-31-19-17-16-18-20-31)42(60)52(13)25(6)39(57)47-24(5)41(59)51(12)26(7)40(58)50-35/h16-20,22-24,26-28,32-38,56H,6,21H2,1-5,7-15H3,(H,47,57)(H,48,54)(H,49,55)(H,50,58)/t24-,26-,27+,28+,32+,33-,34-,35-,36-,37+,38+/m0/s1

InChiKey:

QVYLWCAYZGFGNF-WBWCVGBTSA-N

Long Description:

Chemical. CAS: 568580-02-9. Formula: C46H69N7O15. MW: 960.1. Cyclic depsipeptide composed of unique amino acids differing from normal amino acids. Membrane permeable, potent and selective Galphaq family inhibitor. Inhibits the signal transduction of Galphaq, Galpha11 and Galpha14 (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 Galphaq-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. Galphaq signaling has been shown to regulate brown/beige adipocytes using the structurally similar specific Galphaq 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 Galphaq family inhibitors and were for long time only restricted accessible. The commercial availablilty of YM-254890 might give further insights into Galphaq family singaling processes.

MDL:

MFCD09832722

Molecular Formula:

C46H69N7O15

Molecular Weight:

960.1

Package Type:

Plastic Vial

Product Description:

Cyclic depsipeptide composed of unique amino acids differing from normal amino acids. Membrane permeable, potent and selective Galphaq family inhibitor. Acts in both in vivo and in vitro systems. Inhibits the signal transduction of Galphaq, Galpha11 and Galpha14 (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 Galphaq-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. Galphaq signaling has been shown to regulate brown/beige adipocytes using the structurally similar specific Galphaq 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 Galphaq family inhibitors and were for long time only restricted accessible. The commercial availability of YM-254890 might give further insights into Galphaq family signaling processes.

Purity:

>95% (HPLC)

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

Solubility Chemicals:

Soluble in DMSO (10mg/ml).

Source / Host:

Isolated from Chromobacterium sp. QS3666 strain.

Transportation:

Non-hazardous

UNSPSC Category:

Natural Products/Extracts

UNSPSC Number:

12352200

Use & Stability:

Stable for at least 2 years after receipt when stored at -20°C.

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, Galpha/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)

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