Indolactam V

Indolactam V is an activator of protein kinase C. It induces changes in muscarinic receptor functions.

Product information

CAS Number: 90365-57-4

Molecular Weight: 301.38

Formula: C17H23N3O2

Synonym:

Indolactam-V

(-)-Indolactam V

(-)-ILV

Chemical Name: (2S,5S)-1,2,4,5,6,8-Hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-3H-pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one

Smiles: CC(C)[C@H]1C(=O)N[C@@H](CC2=CNC3=CC=CC(=C23)N1C)CO

InChiKey: LUZOFMGZMUZSSK-LRDDRELGSA-N

InChi: 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

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

(-)-Indolactam V is a PKC activator, with Kis of 3.36 nM, 1.03 μM for η-CRD2 (PKCη surrogate peptide), γ-CRD2 (PKCγ surrogate peptide), and has antitumor activity. (-)-Indolactam V shows Kds of 5.5 nM (η-C1B), 7.7 nM (ε-C1B), 8.3 nM (δ-C1B), 18.9 nM (β-C1A-long), 20.8 nM (α-C1A-long), 137 nM (β-C1B), 138 nM (γ-C1A), 213 nM (γ-C1B), respectively. (-)-Indolactam V (20 nM-5 μM) dose-dependently affects multiple hESC lines, such as HUES 2, 4 and 8. (-)-Indolactam V also increases the mRNA levels of Pdx1, HNF6, PTF1A, SOX9, HB9 and PROX1. In addition, (-)-Indolactam V (300 nM) functions in both mouse and human cells and confirms that some signals for pancreatic development.

References:

1. Stein J, Stahn S, Neudörfl JM, Sperlich J, Schmalz HG, Teusch N. Synthetic Indolactam V Analogues as Inhibitors of PAR2-Induced Calcium Mobilization in Triple-Negative Breast Cancer Cells. ChemMedChem. 2018 Jan 22;13(2):147-154. doi: 10.1002/cmdc.201700640. Epub 2018 Jan 4. PubMed PMID: 29195005.
2. Scavuzzo MA, Yang D, Borowiak M. Organotypic pancreatoids with native mesenchyme develop Insulin producing endocrine cells. Sci Rep. 2017 Sep 7;7(1):10810. doi: 10.1038/s41598-017-11169-1. PubMed PMID: 28883507; PubMed Central PMCID: PMC5589819.
3. Haynes-Smith J, Diaz I, Billingsley KL. Modular Total Synthesis of Protein Kinase C Activator (-)-Indolactam V. Org Lett. 2016 May 6;18(9):2008-11. doi: 10.1021/acs.orglett.6b00614. Epub 2016 Apr 13. PubMed PMID: 27074538.
4. Mori T, Zhang L, Awakawa T, Hoshino S, Okada M, Morita H, Abe I. Manipulation of prenylation reactions by structure-based engineering of bacterial indolactam prenyltransferases. Nat Commun. 2016 Mar 8;7:10849. doi: 10.1038/ncomms10849. PubMed PMID: 26952246; PubMed Central PMCID: PMC4786772.
5. Glover KP, Chen Z, Markell LK, Han X. Synergistic Gene Expression Signature Observed in TK6 Cells upon Co-Exposure to UVC-Irradiation and Protein Kinase C-Activating Tumor Promoters. PLoS One. 2015 Oct 2;10(10):e0139850. doi: 10.1371/journal.pone.0139850. eCollection 2015. PubMed PMID: 26431317; PubMed Central PMCID: PMC4592187.

Products are for research use only. Not for human use.