(-)-Nutlin-3 (CAS 675576-98-4) | Cayman Chemical
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(−)-Nutlin-3

Item № 18585
CAS № 675576-98-4
Purity ≥98%
product image
                (CAS 675576-98-4)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $75.00 0.00
     5 mg $188.00 0.00
     10 mg $338.00 0.00
     25 mg $750.00 0.00

Pricing updated 2019-01-16. Prices are subject to change without notice.

Description
Synonyms
  • Nutlin 3a

The protein p53, often called the ‘guardian of the genome,’ is a transcription factor that is activated in response to cellular stress (low oxygen levels, heat shock, DNA damage, etc.) and acts to prevent further proliferation of the stressed cell by promoting cell cycle arrest or apoptosis.1,2 Its role as a tumor suppressor is evident by the observation that approximately 50% of human tumors have mutated or non-functional p53. MDM2, a key negative regulator of p53, which is over-expressed in many human tumors, functions by binding to and targeting p53 for proteasomal degradation. Nutlin-3 is a potent inhibitor of p53-MDM2 interaction.3 (−)-Nutlin-3 is arbitrarily referred to as enantiomer a because it appears as the first peak from chiral purification of racemic nutlin-3 and its absolute stereocenter assignment is not known. It potently inhibits MDM2-p53 binding with an IC50 value of 0.09 µM, induces the expression of p53-regulated genes, and exhibits potent antiproliferative activity in cells with functional p53, but not in cells with mutated p53.3 (−)-Nutlin-3 inhibits the proliferation of exponentially growing human skin and murine fibroblasts with IC50 values of 2.2 and 1.3 µM, respectively3, and induces substantial tumor shrinkage in mice expressing LnCaP, 22Rv1 or MHM cancer cell lines when treated orally with a 200 mg/kg dose twice daily for two weeks.4

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Technical Information
Formal Name
4-[[(4S,5R)-4,5-bis(4-chlorophenyl)-4,5-dihydro-2-[4-methoxy-2-(1-methylethoxy)phenyl]-1H-imidazol-1-yl]carbonyl]-2-piperazinone
CAS Number
675576-98-4
Synonyms
  • Nutlin 3a
Molecular Formula
C30H30Cl2N4O4
Formula Weight
581.5
Purity
≥98%
Formulation
A crystalline solid
SMILES
ClC1=CC=C([C@@H]2[C@H](C3=CC=C(Cl)C=C3)N=C(C4=CC=C(OC)C=C4OC(C)C)N2C(N5CCN([H])C(C5)=O)=O)C=C1
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+/m0/s1
InChI Key
BDUHCSBCVGXTJM-WUFINQPMSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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References & Product Citations
Product Description References

1. El-Deiry, W.S. The p53 pathway and cancer therapy Cancer Journal 11, 229-236 (1998).

2. Lane, D.P., and Hupp, T.R. Drug discovery and p53 Drug Discovery Today 8(8), 347-355 (2003).

3. Vassilev, L.T., Vu, B.T., Graves, B., et al. In vivo activation of the p53 pathway by small-molecule antagonists of MDM2 Science 303, 844-848 (2004).

4. Tovar, C., Rosinski, J., Filipovic, Z., et al. Small-molecule MDM2 antagonists reveal aberrant p53 signaling in cancer: Implications for therapy Proceedings of the National Academy of Sciences of the United States of America 103(6), 1888-1893 (2006).

Product Citations

Jewett, K.A., Christian, C.A., Bacos, J.T., et al. Feedback modulation of neural network synchrony and seizure susceptibility by Mdm2-p53-Nedd4-2 signaling Mol. Brain 9(32), (2016).

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