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SML1409

Sigma-Aldrich

Madrasin

≥98% (HPLC)

Synonym(s):

2-(7-Methoxy-4-methyl-quinazolin-2-ylamino)-5,6-dimethyl-3H-pyrimidin-4-one, 2-[(7-Methoxy-4-methyl-2-quinazolinyl)amino]-5,6-dimethyl-4(1H)-pyrimidinone (9CI), 4(1H)-Pyrimidinone, 2-[(7-methoxy-4-methyl-2-quinazolinyl)amino]-5,6-dimethyl-(9CI), 4(3H)-Pyrimidinone, 2-[(7-methoxy-4-methyl-2-quinazolinyl)amino]-5,6-dimethyl-, DDD00107587, RNAsplicing inhibitor

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About This Item

Empirical Formula (Hill Notation):
C16H17N5O2
CAS Number:
374913-63-0
Molecular Weight:
311.34
MDL number:
MFCD02233199
UNSPSC Code:
12352200
PubChem Substance ID:
329825856
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

, white to dark brown

solubility

DMSO: 0.5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

CC1=NC(NC(NC(C)=C2C)=NC2=O)=NC3=CC(OC)=CC=C31

InChI

1S/C16H17N5O2/c1-8-9(2)17-16(20-14(8)22)21-15-18-10(3)12-6-5-11(23-4)7-13(12)19-15/h5-7H,1-4H3,(H2,17,18,19,20,21,22)

InChI key

QQJIYKXTEMDJFM-UHFFFAOYSA-N

Application

Madrasin has been used as a spliceosome inhibitor to inhibit pre-mRNA processing in 3T3-L1 cells.

Biochem/physiol Actions

Madrasin is a potent and cell penetrant splicing inhibitor that interferes with the early stages of spliceosome assembly. Madrasin stalls spliceosome assembly at the A complex.
Madrasin is considered toxic to the cell at a higher concentration. At its minimal concentration, madrasin is known to induce subnuclear protein localization and cause cell cycle arrest.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

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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Andrea Pawellek et al.
The Journal of biological chemistry, 289(50), 34683-34698 (2014-10-05)
Eukaryotic pre-mRNA splicing is an essential step in gene expression for all genes that contain introns. In contrast to transcription and translation, few well characterized chemical inhibitors are available with which to dissect the splicing process, particularly in cells. Therefore
Andrey A Parkhitko et al.
PLoS genetics, 17(2), e1009354-e1009354 (2021-02-17)
The RB1 tumor suppressor is recurrently mutated in a variety of cancers including retinoblastomas, small cell lung cancers, triple-negative breast cancers, prostate cancers, and osteosarcomas. Finding new synthetic lethal (SL) interactions with RB1 could lead to new approaches to treating

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