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Nutlin-3b (675576-97-3)

Nutlin-3b is a p53/MDM2 antagonist or inhibitor with IC50 value of 13.6 μM, 150-fold less potent (+)-enantiomer of Nutlin-3 as in comparison with opposite (-)-enantiomer Nutlin-3a…

Not Intended for Therapeutic Use. For research use only.

CAS: 675576-97-3 Category

Nutlin-3b (675576-97-3) Description:

Nutlin-3b is a MDM2/p53 antagonist or inhibitor with IC50 of 13.6 μM.Nutlin-3b is a 150-fold less potent (+)-enantiomer of Nutlin-3 as p53 MDM2 antagonist or inhibitor, in comparison with more potent opposite (-)-enantiomer Nutlin-3a. It is useful as a negative control for non-Mdm2 related cellular activities. Nutlin-3b is useful as a negative control s for non-MDM2-related cellular activities. Nutlin-3a induces the expression of MDM2 and p21 (but not p53) only in cells with wild-type p53. Nutlin-3b has no effect regardless of the p53 status of the cells. Only the active enantiomer Nutlin-3a shows a potent antiproliferative activity and clear separation of potency between the cells harboring wild-type p53 and those harboring mutant p53. The potency of Nutlin-3b is much lower in the wild-type p53 cells and nearly identical to the potency of Nutlin-3a against the mutant p53 cells. After 48 hours of exposure to the Nutlin-3a, 45% of the cell population became TUNEL positive, but cells treated with the Nutlin-3b are indistinguishable from the untreated controls.

Nutlin-3b (675576-97-3) Specifications:

Product Name Nutlin-3b
Synonym Nutlin 3b; Nutlin (3b); Nutlin-3B; 675576-97-3
Chemical Name 4-[[(4R,5S)-4,5-bis(4-chlorophenyl)-4,5-dihydro-2-[4-methoxy-2-(1-methylethoxy)phenyl]-1H-imidazol-1-yl]carbonyl]-2-piperazinone
Drug Class Inhibitor
Purity ≥98% (HPLC)
CAS Number 675576-97-3
Molecular Formula C30H30Cl2N4O4
Molecular Weight 581.5
Monoisotopic Mass 580.164 g/mol
MDL number N/A
InChIKey BDUHCSBCVGXTJM-IZLXSDGUSA-N
InChi Code InChI=1S/C30H30Cl2N4O4/c1-18(2)40-25-16-23(39-3)12-13-24(25)29-34-27(19-4-8-21(31)9-5-19)28(20-6-10-22(32)11-7-20)36(29)30(38)35-15-14-33-26(37)17-35/h4-13,16,18,27-28H,14-15,17H2,1-3H3,(H,33,37)/t27-,28+/m1/s1
SMILES CC(C)OC1=C(C=CC(=C1)OC)C2=NC(C(N2C(=O)N3CCNC(=O)C3)C4=CC=C(C=C4)Cl)C5=CC=C(C=C5)Cl
Form Solid Powder
Color White to off-white
Solubility  Soluble in DMSO (>14 mg/ml)
Storage Temp.  -20°C
Shelf life >2 years if stored properly
Handling Protect from air and light
Application A potent inhibitor of p53-Mdm2 interaction

 


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RIDADR NONH for all modes of transport

References:

[1]. Ye F, Lattif AA, Xie J, Weinberg A, Gao S. Nutlin-3 induces apoptosis, disrupts viral latency and inhibits expression of angiopoietin-2 in Kaposi sarcoma tumor cells. Cell Cycle. 2012 Apr 1;11(7):1393-9. Epub 2012 Apr 1.

[2]. Shin JS, Ha JH, He F, Muto Y, Ryu KS, Yoon HS, Kang S, Park SG, Park BC, Choi SU, Chi SW. Structural insights into the dual-targeting mechanism of Nutlin-3. Biochem Biophys Res Commun. 2012 Mar 30;420(1):48-53.

[3]. Gasparini C, Tommasini A, Zauli G. The MDM2 inhibitor Nutlin-3 modulates dendritic cell-induced T cell proliferation. Hum Immunol. 2012 Apr;73(4):342-5.

[4]. Ma T, Yamada S, Ichwan SJ, Iseki S, Ohtani K, Otsu M, Ikeda MA. Inability of p53-reactivating compounds Nutlin-3 and RITA to overcome p53 resistance in tumor cells deficient in p53Ser46 phosphorylation. Biochem Biophys Res Commun. 2012 Jan 20;417(3):931-7.

[5]. Vatsyayan R, Singhal J, Nagaprashantha LD, Awasthi S, Singhal SS. Nutlin-3 enhances sorafenib efficacy in renal cell carcinoma. Mol Carcinog. 2011 Oct 17. doi: 10.1002/mc.20875.