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SML0569

Sigma-Aldrich

RO-3306

≥98% (HPLC), powder, CDK1 inhibitor

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

product name

RO-3306, ≥98% (HPLC)

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 Code

11 - Combustible Solids

WGK

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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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)
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)
Alina Bluhm et al.
Nucleic acids research, 47(4), 1896-1907 (2019-01-11)
Telomeres are nucleoprotein structures at the ends of linear chromosomes and present an essential feature for genome integrity. Vertebrate telomeres usually consist of hexameric TTAGGG repeats, however, in cells that use the alternative lengthening of telomeres (ALT) mechanism, variant repeat
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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