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SML0569

Sigma-Aldrich

RO-3306

≥98% (HPLC)

Synonym(s):

(5Z)-5-Quinolin-6-ylmethylene-2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one, 5-(6-Quinolinylmethylene)-2-[(2-thienylmethyl)amino]-4(5H)-thiazolone

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About This Item

Empirical Formula (Hill Notation):
C18H13N3OS2
CAS Number:
872573-93-8
Molecular Weight:
351.45
MDL number:
MFCD17392573
UNSPSC Code:
12352200
PubChem Substance ID:
329825559
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

off-white to brown

solubility

DMSO: 5 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C1N=C(NCC2=CC=CS2)S/C1=C\C3=CC4=C(C=C3)N=CC=C4

InChI

1S/C18H13N3OS2/c22-17-16(24-18(21-17)20-11-14-4-2-8-23-14)10-12-5-6-15-13(9-12)3-1-7-19-15/h1-10H,11H2,(H,20,21,22)/b16-10-

InChI key

XOLMRFUGOINFDQ-YBEGLDIGSA-N

Application

RO-3306 has been used:
  • To study the significance of CA4-mediated cytotoxicity in mitotic arrest
  • In cell cycle synchronization to conduct a study on proteomics
  • As a CDK1 inhibitor, to prevent early mitotic entry

Biochem/physiol Actions

CDK1 (cyclin dependent kinase 1) is considered to be the “master switch” in cell division, which maintains the mitotic state of cells.
RO-3306 is a selective ATP-competitive inhibitor of CDK1. It inhibites CDK1 cyclin B1 activity with Ki of 35 nM, nearly 10-fold selectivity relative to CDK2/cyclin E and over 50-fold relative to CDK4/cyclin D. RO-3306 has been used to cause cell cycle arrest at the G2/M boundary.

Features and Benefits

This compound is featured on the CDKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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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Visualization of human karyopherin beta-1/importin beta-1 interactions with protein partners in mitotic cells by co-immunoprecipitation and proximity ligation assays.
Francesco L, et al.
Scientific Reports, 8(1), 1850-1850 (2018)
Tamara B Garcia et al.
Leukemia research, 64, 30-33 (2017-11-28)
Inhibition of WEE1 is emerging as a promising chemosensitization strategy in many cancers including acute leukemia. Our lab and others have demonstrated that a small-molecule inhibitor of WEE1, AZD1775, sensitizes acute leukemia cells to cytarabine; however, a mechanism of combinatorial
Selective small-molecule inhibitor reveals critical mitotic functions of human CDK1.
Vassilev L T, et al.
Proceedings of the National Academy of Sciences of the USA, 103(28), 10660-10665 (2006)
Structurally simplified biphenyl combretastatin A4 derivatives retain in vitro anti-cancer activity dependent on mitotic arrest.
Tarade D, et al.
PLoS ONE, 12(3), e0171806-e0171806 (2017)
BRCA2 suppresses replication stress-induced mitotic and G1 abnormalities through homologous recombination.
Feng W and Jasin M
Nature Communications, 8(1), 525-525 (2017)
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Articles

Cyclin-dependent Kinases (CDKs)

Cyclin dependent kinases (CDKs) are typical serine/threonine kinases that display the 11 subdomains shared by all kinases. The complete sequence of the Homo sapiens genome shows that among the ~30,000 predicted genes, there are 13 CDKs and 25 cyclins. Eleven CDKS and their associated cyclins have been characterized in man.

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