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I0661

Sigma-Aldrich

(−)-Indolactam V

≥96% (HPLC)

Synonym(s):

(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

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About This Item

Empirical Formula (Hill Notation):
C17H23N3O2
CAS Number:
90365-57-4
Molecular Weight:
301.38
MDL number:
MFCD00151197
UNSPSC Code:
12352200
PubChem Substance ID:
329815323
NACRES:
NA.77

Assay

≥96% (HPLC)

form

powder

color

white

storage temp.

−20°C

SMILES string

CC(C)[C@@H]1N(C)c2cccc3[nH]cc(C[C@@H](CO)NC1=O)c23

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

InChI key

LUZOFMGZMUZSSK-LRDDRELGSA-N

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.
(−)-Indolactam V is naturally present in Streptoverticillium blastmyceticum. It serves as a precursor to the teleocidin class which are alkaloids. It is a the pharmacophore of lyngbyatoxin and teleocidins.

Features and Benefits

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yu Nakagawa et al.
Journal of the American Chemical Society, 127(16), 5746-5747 (2005-04-21)
The CH/pi interaction between the indole ring of indolactam-V (IL-V) and the hydrogen atom at position 4 of Pro-11 of the PKCdelta C1B domain was evaluated using the mutant peptide of the PKCdelta C1B domain, in which the CH/pi interaction
Ryo C Yanagita et al.
Journal of medicinal chemistry, 51(1), 46-56 (2007-12-13)
Conventional and novel protein kinase C (PKC) isozymes are the main targets of tumor promoters. We developed 1-hexylindolactam-V10 ( 5) as a selective activator for novel PKC isozymes that play important roles in various cellular processes related to tumor promotion
Kazuhiro Irie et al.
Current pharmaceutical design, 10(12), 1371-1385 (2004-05-12)
Protein kinase C (PKC) isozymes (alpha, betaI, betaII, gamma, delta, epsilon, eta, theta) are major receptors of tumor promoters and also play a crucial role in cellular signal transduction via the second messenger, 1,2-diacyl-sn-glycerol (DG). Each isozyme of PKC is
Synthesis of (-)-Epi-Indolactam V by an Intramolecular Buchwald-Hartwig C-N Coupling Cyclization Reaction
Mari M, et al.
The Journal of Organic Chemistry, 78(15), 7727-7734 (2013)
Kazuhiro Irie et al.
Chemical record (New York, N.Y.), 5(4), 185-195 (2005-07-26)
Tumor promoters such as phorbol esters bind strongly to protein kinase C (PKC) isozymes to induce their activation. Since each PKC isozyme is involved in diverse biological events in addition to tumor promotion, the isozymes serve as promising therapeutic targets.
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Protein Kinase C (PKC)

Protein kinase C (PKC) is an AGC kinase that phosphorylates serine and threonine residues in many target proteins.

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