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F7804

Sigma-Aldrich

Fascaplysin chloride hydrate

≥98% (HPLC), solid

Synonym(s):

12,13-Dihydro-13-oxopyrido[1,2-a:3,4-b′]diindol-5-ium chloride, Fascaplysine hydrate

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About This Item

Empirical Formula (Hill Notation):
C18H11ClN2O · xH2O
CAS Number:
114719-57-2
Molecular Weight:
306.75 (anhydrous basis)
MDL number:
MFCD09752600
UNSPSC Code:
12352200

assay

≥98% (HPLC)

form

solid

color

brick red

solubility

H2O: <2 mg/mL
DMSO: ~20 mg/mL

storage temp.

2-8°C

SMILES string

[Cl-].[H]O[H].O=C1c2ccccc2-[n+]3ccc4c([nH]c5ccccc45)c13

InChI

1S/C18H10N2O.ClH.H2O/c21-18-13-6-2-4-8-15(13)20-10-9-12-11-5-1-3-7-14(11)19-16(12)17(18)20;;/h1-10H;1H;1H2

InChI key

WPIOPGXRERNYSI-UHFFFAOYSA-N

Biochem/physiol Actions

Originally isolated from the marine sponge Thorectandra sp., fascaplysin chloride is a selective, potent inhibitor of cyclin dependent kinase 4/cyclin D1 (IC50 = 0.35 μM). It is significantly less selective for Cdk6/D1 (IC50 = 3.4 μM) and not selective for the other Cdks and tyrosine kinases.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Sachin Mahale et al.
Bioorganic chemistry, 34(5), 287-297 (2006-08-15)
Tryptamine derivatives, a new structural class of cyclin dependent kinase 4 inhibitors, have been identified during extensive biological screening of synthetic molecules. The molecules were synthesized based on the structure of fascaplysin, which is not only a specific inhibitor of
R Soni et al.
Biochemical and biophysical research communications, 275(3), 877-884 (2000-09-07)
Small chemical molecules that interfere with biological proteins could be useful for gaining insight into the complex biochemical processes in mammalian cells. Cdk4 is a key protein whose activity is required not only for emergence of cells from quiescence but
A M Popov et al.
Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic], 36(1), 12-14 (1991-01-01)
Various aspects of the physiological activity of fascaplysine, a pigment from tropic sea sponges, were studied. One of the fragments of the chemical structure of the pigment is the indole ring. Ehrlich tumor cells, murine lymphocytes and erythrocytes were used
Carine Aubry et al.
Chemical communications (Cambridge, England), (15)(15), 1696-1697 (2004-07-28)
The first biologically active non-planar analogues of the toxic anti-cancer agent, fascaplysin, have been produced; we present the design, synthesis and biological activity of three tryptamine derivatives.
Nicole M R Schmitz et al.
The American journal of pathology, 169(3), 1074-1079 (2006-08-29)
Cyclin-dependent kinases (CDKs) successively phosphorylate the retinoblastoma protein (RB) at the restriction point in G1 phase. Hyperphosphorylation results in functional inactivation of RB, activation of the E2F transcriptional program, and entry of cells into S phase. RB unphosphorylated at serine
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