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90365-57-4

90365-57-4 structure
90365-57-4 structure
  • Name: (-)-Indolactam V
  • Chemical Name: (-)-Indolactam V,(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
  • CAS Number: 90365-57-4
  • Molecular Formula: C17H23N3O2
  • Molecular Weight: 301.383
  • Catalog: Research Areas Cancer
  • Create Date: 2017-02-03 05:37:51
  • Modify Date: 2024-01-03 11:14:58
  • (-)-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 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), and has antitumor activity.

Name (-)-Indolactam V,(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
Synonyms (2S,5S)-5-(hydroxymethyl)-1-methyl-2-(propan-2-yl)-1,2,4,5,6,8-hexahydro-3H-[1,4]diazonino[7,6,5-cd]indol-3-one
3H-1,4-Diazonino[7,6,5-cd]indol-3-one, 1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-, (2S,5S)-
(-)-indolactam
Indolactam V
(2S,5S)-5-(Hydroxymethyl)-2-isopropyl-1-methyl-1,2,4,5,6,8-hexahydro-3H-[1,4]diazonino[7,6,5-cd]indol-3-one
Description (-)-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 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), and has antitumor activity.
Related Catalog
Target

PKCη-CRD2:3.36 nM (Ki)

PKCη-C1B:5.5 nM (Kd)

PKCε-C1B:7.7 nM (Kd)

PKCδ-C1B:8.3 nM (Kd)

PKCθ-C1B:8.7 nM (Kd)

PKCβ-C1A-long:18.9 nM (Kd)

PKCα-C1A-long:20.8 nM (Kd)

PKCβ-C1B:137 nM (Kd)

PKCγ-C1A:138 nM (Kd)

PKCγ-C1B:213 nM (Kd)

PKCγ-CRD2:1030 nM (Ki)

PKCδ-C1A:1900 nM (Kd)

PKCη-C1A:3770 nM (Kd)

PKCα-C1B-long:4000 nM (Kd)

PKCε-C1A:4110 nM (Kd)

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[1]. (-)-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[2]. (-)-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[3].
Cell Assay For induced differentiation to endocrine or exocrine cells, the (-)-Indolactam V (300 nM)-treated populations are cultured in DMEM/F12 supplemented with 1 N2, 2 mg/mL albumin fraction V and 10 ng/mL bovine FGF for the first 4 d. 10 mM nicotinamide is then added and maintained for an additional 8 d, changing the medium every 3 d[3].
References

[1]. Nakagawa Y, et al. Synthesis and biological activities of indolactone-V, the lactone analogue of the tumor promoter (-)-indolactam-V. Biosci Biotechnol Biochem. 1997 Aug;61(8):1415-7.

[2]. Masuda A, et al. Binding selectivity of conformationally restricted analogues of (-)-indolactam-V to the C1 domains of protein kinase C isozymes. Biosci Biotechnol Biochem. 2002 Jul;66(7):1615-7.

[3]. Chen S, et al. A small molecule that directs differentiation of human ESCs into the pancreatic lineage. Nat Chem Biol. 2009 Apr;5(4):258-65.

Density 1.2±0.1 g/cm3
Boiling Point 584.0±50.0 °C at 760 mmHg
Molecular Formula C17H23N3O2
Molecular Weight 301.383
Flash Point 307.0±30.1 °C
Exact Mass 301.179016
PSA 68.36000
LogP 0.75
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.590

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UY8547000
CHEMICAL NAME :
3H-Pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one, 1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1- methyl-2-(1-methylethyl)-, (2S-(2R*,5R*))-
CAS REGISTRY NUMBER :
90365-57-4
LAST UPDATED :
199612
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C17-H23-N3-O2
MOLECULAR WEIGHT :
301.43

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1250 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 44,1029,1991
RIDADR NONH for all modes of transport