5HPP-33

• CAT Number: I014011
• CAS Number: 105624-86-0
• Molecular Formula: C20H21NO3
• Molecular Weight: 323.39
• Purity: ≥95%
• Synonyms: 5HPP-33; 5HPP 33; 5HPP33;;2-[2,6-Di(propan-2-yl)phenyl]-5-hydroxyisoindole-1,3-dione
• Solubility: Soluble in DMSO
• InChI: InChI=1S/C20H21NO3/c1-11(2)14-6-5-7-15(12(3)4)18(14)21-19(23)16-9-8-13(22)10-17(16)20(21)24/h5-12,22H,1-4H3
• InChIKey: LAKWINYVWJPHQW-UHFFFAOYSA-N
• SMILES: O=C1N(C2=C(C(C)C)C=CC=C2C(C)C)C(C3=C1C=CC(O)=C3)=O

5HPP-33 is an antiproliferative and antimitotic microtubule-stabilizer.

Reference

1: Ellis-Hutchings RG, Settivari RS, McCoy AT, Kleinstreuer N, Franzosa J, Knudsen TB, Carney EW. Embryonic vascular disruption adverse outcomes: Linking high throughput signaling signatures with functional consequences. Reprod Toxicol. 2017 Jun;70:82-96. doi: 10.1016/j.reprotox.2017.05.005. Epub 2017 May 17. PubMed PMID: 28527947.2: Ellis-Hutchings RG, Settivari RS, McCoy AT, Kleinstreuer N, Franzosa J, Knudsen TB, Carney EW. Embryonic vascular disruption adverse outcomes: Linking high-throughput signaling signatures with functional consequences. Reprod Toxicol. 2017 Apr 13;71:16-31. doi: 10.1016/j.reprotox.2017.04.003. [Epub ahead of print] PubMed PMID: 28414088.3: Rashid A, Kuppa A, Kunwar A, Panda D. Thalidomide (5HPP-33) suppresses microtubule dynamics and depolymerizes the microtubule network by binding at the vinblastine binding site on tubulin. Biochemistry. 2015 Mar 31;54(12):2149-59. doi: 10.1021/bi501429j. Epub 2015 Mar 17. PubMed PMID: 25747795.4: Pandit B, Hu Z, Chettiar SN, Zink J, Xiao Z, Etter JP, Bhasin D, Li PK. Structure-activity relationship studies of thalidomide analogs with a taxol-like mode of action. Bioorg Med Chem Lett. 2013 Dec 15;23(24):6902-4. doi: 10.1016/j.bmcl.2013.09.084. Epub 2013 Oct 4. PubMed PMID: 24169233.5: Kleinstreuer N, Dix D, Rountree M, Baker N, Sipes N, Reif D, Spencer R, Knudsen T. A computational model predicting disruption of blood vessel development. PLoS Comput Biol. 2013 Apr;9(4):e1002996. doi: 10.1371/journal.pcbi.1002996. Epub 2013 Apr 4. PubMed PMID: 23592958; PubMed Central PMCID: PMC3616981.6: Shimura M, Yamamoto M, Fujii G, Takahashi M, Komiya M, Noma N, Tanuma S, Yanaka A, Mutoh M. Novel compound SK-1009 suppresses interleukin-6 expression through modulation of activation of nuclear factor-kappaB pathway. Biol Pharm Bull. 2012;35(12):2186-91. Epub 2012 Sep 27. PubMed PMID: 23018603.7: Kizaki M, Hashimoto Y. New tubulin polymerization inhibitor derived from thalidomide: implications for anti-myeloma therapy. Curr Med Chem. 2008;15(8):754-65. Review. PubMed PMID: 18393844.8: Iguchi T, Yachide-Noguchi T, Hashimoto Y, Nakazato S, Sagawa M, Ikeda Y, Kizaki M. Novel tubulin-polymerization inhibitor derived from thalidomide directly induces apoptosis in human multiple myeloma cells: possible anti-myeloma mechanism of thalidomide. Int J Mol Med. 2008 Feb;21(2):163-8. PubMed PMID: 18204782.9: de-Blanco EJ, Pandit B, Hu Z, Shi J, Lewis A, Li PK. Inhibitors of NF-kappaB derived from thalidomide. Bioorg Med Chem Lett. 2007 Nov 1;17(21):6031-5. Epub 2007 Feb 2. PubMed PMID: 17845850.10: Aoyama H, Noguchi T, Misawa T, Nakamura T, Miyachi H, Hashimoto Y, Kobayashi H. Development of tubulin-polymerization inhibitors based on the thalidomide skeleton. Chem Pharm Bull (Tokyo). 2007 Jun;55(6):944-9. PubMed PMID: 17541201.11: Li PK, Pandit B, Sackett DL, Hu Z, Zink J, Zhi J, Freeman D, Robey RW, Werbovetz K, Lewis A, Li C. A thalidomide analogue with in vitro antiproliferative, antimitotic, and microtubule-stabilizing activities. Mol Cancer Ther. 2006 Feb;5(2):450-6. PubMed PMID: 16505120.12: Noguchi T, Fujimoto H, Sano H, Miyajima A, Miyachi H, Hashimoto Y. Angiogenesis inhibitors derived from thalidomide. Bioorg Med Chem Lett. 2005 Dec 15;15(24):5509-13. Epub 2005 Sep 23. PubMed PMID: 16183272.13: Noguchi T, Miyachi H, Katayama R, Naito M, Hashimoto Y. Cell differentiation inducers derived from thalidomide. Bioorg Med Chem Lett. 2005 Jul 1;15(13):3212-5. PubMed PMID: 15936192.14: Inatsuki S, Noguchi T, Miyachi H, Oda S, Iguchi T, Kizaki M, Hashimoto Y, Kobayashi H. Tubulin-polymerization inhibitors derived from thalidomide. Bioorg Med Chem Lett. 2005 Jan 17;15(2):321-5. PubMed PMID: 15603947.