(-)-Indolactam V

Product Name(-)-Indolactam V
CAS90365-57-4
MFC17H23N3O2
MW301.38
EINECS
MOL File90365-57-4.mol

Chemical Properties

Boiling point	584.0±50.0 °C(Predicted)
Density	1.166±0.06 g/cm3(Predicted)
storage temp.	-20°C
solubility	DMSO: >10mg/mL, clear
form	white powder
pka	14.39±0.10(Predicted)
color	White to light yellow
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
InChI	1S/C17H23N3O2/c1-10(2)16-17(22)19-12(9-21)7-11-8-18-13-5-4-6-14(15(11)13)20(16)3/h4-6,8,10,12,16,18,21H,7,9H2,1-3H3,(H,19,22)/t12-,16-/m0/s1
InChIKey	LUZOFMGZMUZSSK-LRDDRELGSA-N
SMILES	CC(C)[C@@H]1N(C)c2cccc3[nH]cc(C[C@@H](CO)NC1=O)c23

Safety Information

WGK Germany	3
RTECS	UY8547000
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Indolactam V (-) (90365-57-4) is a PKC activator acting at the phorbol ester binding site.1,2Directs differentiation of human and mouse ESCs to pancreatic cells.3 May be used, along with other agents, to differentiate human iPS cells into glucose-responsive insulin-secreting progeny.4Increases regulator of G protein signaling 2 (RGS2) protein levels, a protein that regulates GPCR signaling.5

Uses

(-)-Indolactam V is an indole alkaloid compound which activates protein kinase C (PKC). Weak tumor promoter. Also directs differentiation of human embryonic stem cells, potentially into pancreatic lineage allowing for an effective diabetes therapy.

Definition

ChEBI: (-)-indolactam V is a 9-membered ring that is a potent protein kinase C activator

Biological Activity

Protein kinase C activator. Exhibits tumor promoting activity. Directs differentiation of human embryonic stem cells (ESCs) into pancreatic progenitors.

Biochem/physiol Actions

(-)-Indolactam V is a PKC activator shown to effect differentiation in embryonic stem cells leading to development of pancreatic precursors. It is active in the mouse model.

storage

-20°C (desiccate)

References

[1] H. FUJIKI. Structure-activity studies on synthetic analogues (indolactams) of the tumor promoter teleocidin.[J]. Philosophia (Ramat-Gan, Israel), 1984, 7 1: 866-870. DOI:10.20772/cancersci1959.75.10\_866
[2] JARI HEIKKILÄ Karl E O Å. (−)-Indolactam V activates protein kinase C and induces changes in muscarinic receptor functions in SH-SY5Y human neuroblastoma cells[J]. Biochemical and biophysical research communications, 1989, 162 3: Pages 1207-1213. DOI:10.1016/0006-291x(89)90802-4
[3] SHUIBING CHEN. A small molecule that directs differentiation of human ESCs into the pancreatic lineage[J]. Nature chemical biology, 2009, 5 4: 258-265. DOI:10.1038/nchembio.154
[4] T THATAVA. Indolactam V/GLP-1-mediated differentiation of human iPS cells into glucose-responsive insulin-secreting progeny[J]. Gene Therapy, 2010, 18 3: 283-293. DOI:10.1038/gt.2010.145
[5] AVI RAVEH. Identification of protein kinase C activation as a novel mechanism for RGS2 protein upregulation through phenotypic screening of natural product extracts.[J]. Molecular Pharmacology, 2014, 86 4: 406-416. DOI:10.1124/mol.114.092403

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