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Merck
CN

I0661

(−)-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
NACRES:
NA.77
PubChem Substance ID:
329815323
UNSPSC Code:
12352200
MDL number:
MFCD00151197

Key Documents

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InChI key

LUZOFMGZMUZSSK-LRDDRELGSA-N

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

assay

≥96% (HPLC)

form

powder

color

white

storage temp.

−20°C

Quality Level

100

Biochem/physiol Actions

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000388951
0000382449
0000382449
0000388951
0000130523

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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.
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)
Zhengren Xu et al.
Organic & biomolecular chemistry, 9(7), 2512-2517 (2011-02-23)
The total synthesis of protein kinase C activator (-)-indolactam V (IL-V) has been successfully completed with two separate approaches: From known 4-nitrotryptophan derivative 3 in 8 steps (49% overall yield) and from L-glutamic acid in 12 steps (18% overall yield)
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
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Articles

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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