MB-3 (drug)

MB-3 (drug)
Identifiers
	IUPAC name (2R,3S)-4-methylidene-5-oxo-2-propyloxolane-3-carboxylic acid;
CAS Number	778649-18-6;
PubChem CID	21579153;
ChemSpider	10190941;
ChEBI	CHEBI:190985;
ChEMBL	ChEMBL217676;
Chemical and physical data
Formula	C9H12O4
Molar mass	184.191 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC[C@@H]1[C@H](C(=C)C(=O)O1)C(=O)O;
	InChI InChI=1S/C9H12O4/c1-3-4-6-7(8(10)11)5(2)9(12)13-6/h6-7H,2-4H2,1H3,(H,10,11)/t6-,7+/m1/s1; Key:SRQUTZJZABSZRQ-RQJHMYQMSA-N;

MB-3 is a drug which acts as a potent and selective inhibitor of the histone acetyltransferase enzyme GCN5, which usually functions as a negative modulator of PGC-1α, and so MB-3 acts to indirectly activate PGC-1α. It is used in research into the role of the GCN5/PGC-1α pathway in the regulation of metabolism and cell differentiation.^[1]^[2]^[3]

References

^ Biel M, Kretsovali A, Karatzali E, Papamatheakis J, Giannis A (July 2004). "Design, synthesis, and biological evaluation of a small-molecule inhibitor of the histone acetyltransferase Gcn5". Angewandte Chemie. 43 (30): 3974–6. doi:10.1002/anie.200453879. PMID 15274229.
^ Mai A, Rotili D, Tarantino D, Ornaghi P, Tosi F, Vicidomini C, et al. (November 2006). "Small-molecule inhibitors of histone acetyltransferase activity: identification and biological properties". Journal of Medicinal Chemistry. 49 (23): 6897–907. doi:10.1021/jm060601m. PMID 17154519.
^ Xu H, Zhou Q, Yi Q, Tan B, Tian J, Chen X, et al. (February 2020). "Islet-1 synergizes with Gcn5 to promote MSC differentiation into cardiomyocytes". Scientific Reports. 10 (1): 1817. Bibcode:2020NatSR..10.1817X. doi:10.1038/s41598-020-58387-8. PMC 7000709. PMID 32019948.

This pharmacology-related article is a stub. You can help Wikipedia by expanding it.

[1] Biel M, Kretsovali A, Karatzali E, Papamatheakis J, Giannis A (July 2004). "Design, synthesis, and biological evaluation of a small-molecule inhibitor of the histone acetyltransferase Gcn5". Angewandte Chemie. 43 (30): 3974–6. doi:10.1002/anie.200453879. PMID 15274229.

[2] Mai A, Rotili D, Tarantino D, Ornaghi P, Tosi F, Vicidomini C, et al. (November 2006). "Small-molecule inhibitors of histone acetyltransferase activity: identification and biological properties". Journal of Medicinal Chemistry. 49 (23): 6897–907. doi:10.1021/jm060601m. PMID 17154519.

[3] Xu H, Zhou Q, Yi Q, Tan B, Tian J, Chen X, et al. (February 2020). "Islet-1 synergizes with Gcn5 to promote MSC differentiation into cardiomyocytes". Scientific Reports. 10 (1): 1817. Bibcode:2020NatSR..10.1817X. doi:10.1038/s41598-020-58387-8. PMC 7000709. PMID 32019948.

[1]

[2]

[3]

Identifiers

IUPAC name (2R,3S)-4-methylidene-5-oxo-2-propyloxolane-3-carboxylic acid
CAS Number	778649-18-6
PubChem CID	21579153
ChemSpider	10190941
ChEBI	CHEBI:190985
ChEMBL	ChEMBL217676
Chemical and physical data
Formula	C₉H₁₂O₄
Molar mass	184.191 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCC[C@@H]1[C@H](C(=C)C(=O)O1)C(=O)O
InChI InChI=1S/C9H12O4/c1-3-4-6-7(8(10)11)5(2)9(12)13-6/h6-7H,2-4H2,1H3,(H,10,11)/t6-,7+/m1/s1 Key:SRQUTZJZABSZRQ-RQJHMYQMSA-N

MB-3 (drug)

See also

References