Nutlin-3b

• CAT Number: I004541
• CAS Number: 675576-97-3
• Molecular Formula: C₃₀H₃₀Cl₂N₄O₄
• Molecular Weight: 581.49
• Purity: ≥95%
• Target: MDM2
• Solubility: DMSO 100 mg/ml; Water <1 mg/ml
• Storage: Store at -20°C
• IC50: 13.6 μM
• IUPAC Name: 4-[(4R,5S)-4,5-bis(4-chlorophenyl)-2-(4-methoxy-2-propan-2-yloxyphenyl)-4,5-dihydroimidazole-1-carbonyl]piperazin-2-one
• InChI: 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
• InChIKey: BDUHCSBCVGXTJM-IZLXSDGUSA-N
• 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

Nutlin-3b（Cat No.:I004541）, also known as (+)-Nutlin-3, is a p53/MDM2 antagonist or inhibitor. It exhibits an IC50 value of 13.6 μM. Nutlin-3b is the (+)-enantiomer of Nutlin-3, while Nutlin-3a is the (-)-enantiomer. In vivo, studies have shown that Nutlin-3b is approximately 150 times less effective compared to Nutlin-3a. This difference in efficacy between the two enantiomers highlights the importance of stereochemistry in their interactions with the p53/MDM2 pathway.

Reference

[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.