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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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.
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
Zhenyu Lu et al.
Bioorganic & medicinal chemistry, 19(22), 6604-6607 (2011-06-24)
A new fascaplysin analogue, 3-bromohomofascaplysin A (1), along with two known analogues, homofascaplysin A (2) and fascaplysin (3), were isolated from a Fijian Didemnum sp. ascidian. The absolute configurations of 3-bromohomofascaplysin A (1) and homofascaplysin A (2) were determined via
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