Stauprimide

Stauprimide
Names
	Preferred IUPAC name N-[(12S,13R,14R,16R)-13-Methoxy-12-methyl-5,7-dioxo-6,7,13,14,15,16-hexahydro-5H,12H-17-oxa-11b,16a-diaza-12,16-methanocyclonona[jkl]cyclopenta[e]dibenzo[b,h]-as-indacen-14-yl]-N-methylbenzamide
Identifiers
CAS Number	154589-96-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	24606051;
PubChem CID	46245328;
UNII	T7R6VV8WUL ;
CompTox Dashboard (EPA)	DTXSID601029754 ;
	InChI InChI=1S/C35H28N4O5/c1-35-31(43-3)23(37(2)34(42)18-11-5-4-6-12-18)17-24(44-35)38-21-15-9-7-13-19(21)25-27-28(33(41)36-32(27)40)26-20-14-8-10-16-22(20)39(35)30(26)29(25)38/h4-16,23-24,31H,17H2,1-3H3,(H,36,40,41)/t23-,24-,31-,35+/m1/s1;
	SMILES C[C@@]12[C@@H]([C@@H](C[C@@H](O1)n3c4ccccc4c5c3c6n2c7ccccc7c6c8c5C(=O)NC8=O)N(C)C(=O)c9ccccc9)OC;
Properties
Chemical formula	C35H28N4O5
Molar mass	584.632 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Stauprimide is a semi-synthetic analog of the staurosporine family of indolocarbazoles. Stauprimide was first published in 1994 as part of an extensive structure-activity investigation to improve the selective inhibition of protein kinase C as a potential antitumor agent.^[1] More recently, stauprimide has been shown to increase the efficiency of the directed differentiation of mouse and human embryonic stem cells in synergy with defined extracellular signaling cues. Stauprimide interacts with NME2 (PUF) transcription factor to down-regulate c-Myc expression, leading to differentiation of stem cells.^[2]

References

^ Caravatti, Giorgio; Meyer, Thomas; Fredenhagen, Andreas; Trinks, Uwe; Mett, Helmut; Fabbro, Doriano (1994). "Inhibitory activity and selectivity of staurosporine derivatives towards protein kinase C". Bioorganic & Medicinal Chemistry Letters. 4 (3): 399–404. doi:10.1016/0960-894X(94)80004-9.
^ Zhu, S; Wurdak, H; Wang, J; Lyssiotis, CA; Peters, EC; Cho, CY; Wu, X; Schultz, PG (2009). "A small molecule primes embryonic stem cells for differentiation". Cell Stem Cell. 4 (5): 416–26. doi:10.1016/j.stem.2009.04.001. PMID 19427291.

[1] Caravatti, Giorgio; Meyer, Thomas; Fredenhagen, Andreas; Trinks, Uwe; Mett, Helmut; Fabbro, Doriano (1994). "Inhibitory activity and selectivity of staurosporine derivatives towards protein kinase C". Bioorganic & Medicinal Chemistry Letters. 4 (3): 399–404. doi:10.1016/0960-894X(94)80004-9.

[2] Zhu, S; Wurdak, H; Wang, J; Lyssiotis, CA; Peters, EC; Cho, CY; Wu, X; Schultz, PG (2009). "A small molecule primes embryonic stem cells for differentiation". Cell Stem Cell. 4 (5): 416–26. doi:10.1016/j.stem.2009.04.001. PMID 19427291.

[1]

[2]

See also

References