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C3249

Sigma-Aldrich

CR8

≥95% (HPLC)

Synonym(s):

(2R)-2-[[9-(1-Methylethyl)-6-[[[4-(2-pyridinyl)phenyl]methyl]amino]-9H-purin-2-yl]amino]-butanol-1, (R)-2-(1-Hydroxybut-2-ylamino)-6-[4-(2-pyridyl)phenylmethylamino]-9-iso-propylpurine, C&R8

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About This Item

Empirical Formula (Hill Notation):
C24H29N7O
CAS Number:
294646-77-8
Molecular Weight:
431.53
MDL number:
MFCD18785641
UNSPSC Code:
12352200
PubChem Substance ID:
329775030
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

off-white

solubility

DMSO: ≥10 mg/mL

storage temp.

2-8°C

SMILES string

CC[C@H](CO)Nc1nc(NCc2ccc(cc2)-c3ccccn3)c4ncn(C(C)C)c4n1

InChI

1S/C24H29N7O/c1-4-19(14-32)28-24-29-22(21-23(30-24)31(15-27-21)16(2)3)26-13-17-8-10-18(11-9-17)20-7-5-6-12-25-20/h5-12,15-16,19,32H,4,13-14H2,1-3H3,(H2,26,28,29,30)/t19-/m1/s1

InChI key

HOCBJBNQIQQQGT-LJQANCHMSA-N

Biochem/physiol Actions

CR8 is a potent and selective inhibitor of cyclin dependent kinase (CDK1, 2, 5, 7, and 9). CR8 is a more potent pyridyl analogue of roscovitine (Cat. No. R7772). In comparison to roscovirtine, the compound gains in potency toward CK1, which is involved in amyloid-β formation. The R-CR8 enantiomer is slightly more potent than S. CR8 is around 30 times more potent at cellular assay then roscovitine. Acts as a molecular glue to induce cyclin K degradation.

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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Andrey Shadrin et al.
Microbiology (Reading, England), 158(Pt 11), 2753-2764 (2012-09-15)
The Escherichia coli-infecting bacteriophage T7 encodes a 7 kDa protein, called Gp2, which is a potent inhibitor of the host RNA polymerase (RNAp). Gp2 is essential for T7 phage development. The interaction site for Gp2 on the E. coli RNAp
Dominic P Byrne et al.
The Biochemical journal, 478(4), 735-748 (2021-01-23)
Sulfated carbohydrate metabolism is a fundamental process, which occurs in all domains of life. Carbohydrate sulfatases are enzymes that remove sulfate groups from carbohydrates and are essential to the depolymerisation of complex polysaccharides. Despite their biological importance, carbohydrate sulfatases are
Junfang Wu et al.
Journal of neuroinflammation, 9, 169-169 (2012-07-13)
Traumatic spinal cord injury (SCI) induces secondary tissue damage that is associated with astrogliosis and inflammation. We previously reported that acute upregulation of a cluster of cell-cycle-related genes contributes to post-mitotic cell death and secondary damage after SCI. However, it
Jacob W Skovira et al.
Journal of neuroinflammation, 13(1), 299-299 (2016-12-03)
Traumatic brain injury (TBI) patients in military settings can be exposed to prolonged periods of hypobaria (HB) during aeromedical evacuation. Hypobaric exposure, even with supplemental oxygen to prevent hypoxia, worsens outcome after experimental TBI, in part by increasing neuroinflammation. Cell
Junfang Wu et al.
PloS one, 7(7), e42129-e42129 (2012-08-01)
Apoptosis of post-mitotic neurons plays a significant role in secondary tissue damage following traumatic spinal cord injury (SCI). Activation of E2F1-dependent transcription promotes expression of pro-apoptotic factors, including CDK1; this signal transduction pathway is believed to represent an important mechanism
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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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