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5.32813

UC2288

≥98% (HPLC), solid, p21 inhibitor, Calbiochem®

Synonym(s):

p21 Inhibitor, UC2288, 1-(4-Chloro-3-(trifluoromethyl)phenyl)-3-((1r,4r)-4-(5-(trifluoromethyl)pyridin-2-yloxy)cyclohexyl)urea, trans-1-(4-Chloro-3-trifluoromethyl-phenyl)-3-(4-hydroxy-cyclohexyl)-urea, p21/Cip1/CKI/Waf1 Inhibitor, t-CTTU; UC-2288

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Size/SKUAvailabilityPrice
10 mg
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$282.00

About This Item

Empirical Formula (Hill Notation):
C20H18ClF6N3O2
CAS Number:
1394011-91-6
Molecular Weight:
481.82
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD28139634
Assay:
≥98% (HPLC)
Form:
solid
Storage condition:
OK to freeze, protect from light

$282.00

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Product Name

p21 Inhibitor, UC2288,

assay

≥98% (HPLC)

Quality Segment

100

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

white

solubility

DMSO: 50 mg/mL

storage temp.

2-8°C

SMILES string

O=C(N[C@@H]1CC[C@@H](OC2=CC=C(C=N2)C(F)(F)F)CC1)NC3=CC(C(F)(F)F)=C(Cl)C=C3

InChI

1S/C20H18ClF6N3O2/c21-16-7-4-13(9-15(16)20(25,26)27)30-18(31)29-12-2-5-14(6-3-12)32-17-8-1-11(10-28-17)19(22,23)24/h1,4,7-10,12,14H,2-3,5-6H2,(H2,29,30,31)/t12-,14-

InChI key

ISPSOOYSNVVMMB-MQMHXKEQSA-N

General description

A cell-permeable compound that selectively downregulates the expression of p21 (~10 µM), independent of p53.expression, at either transcription or post-transcriptional level.
A cell-permeable phenylcyclohexyl-urea compound that downregulates cellular p21/Cip1/CKI/Waf1 protein level (by >95% in HCT116 cells after 24 h UC2288 treatment at 2.5 µM), presumably by means of a yet undetermined transcriptional or post-transcriptional regulation without affecting p21 cellular half-life or inhibiting the kinase activities of C-raf, B-rafV600E, or VEGFR2 (IC50 >10 µM). Dual telomerase and p21, but not p16 or p27 (gene = CDKN1A, CDKN2A, CDKN1B, respectively), knockdown/inhibition is demonstrated to effectively kill cancer cells both in vitro (% viability inhibition/% Annexin V+ cells induction = 20%/2% or 77%/55%, respectively, following telomerase inhibition by Imetelstat with or without 2.5 µM UC2288 for 24 h in HCT116 colon cancer cultures) and in mice in vivo (% tumor expansion suppression by UC2288 alone/Imetelstat alone/combined treatment = 13%/42%/90%/HCT116 and 4%/23%/92%/ACHN; 30 mg Imetelstat/kg via i.p. and/or 15 mg UC2288/kg via p.o. 3X/wk for 3 wk) by inducing p53- and E2F1-dependent PUMA expression, while p21 overexpression, p53 inactivation by mutation, shRNA-mediated E2F1 or PUMA downregulation abolishes such synergized cell killing. Likewise, reactivating mutant p53 activitiy by CP-31398 (Cat. No. 506166) treatment is reported to resensitize DLD1 (p53 S241F) and A375.S2 (p53 R273H & P309S) to p21 shRNA- & Imetelstat-induced apoptotic cell death and tumor growth inhibition.

Biochem/physiol Actions

Cell permeable: yes

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Use only fresh DMSO for reconstitution.

Other Notes

Gupta, R., et al. 2014. Proc. Natl. Acad. Sci. USA111, E3062.
Wettersten, H.I., et al. 2013. Cancer Biol. Ther.14, 278.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

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description

-

description

-

description

-

description

-

form

solid

form

solid

form

film

form

solid

assay

≥98% (HPLC)

assay

≥97% (HPLC)

assay

≥96% (HPLC)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: 50 mg/mL

solubility

water: 5 mg/mL, DMSO: 50 mg/mL

solubility

DMSO: 50 mg/mL

solubility

DMSO: 100 mg/mL

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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