WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 561769
CAS#: 105624-86-0
Description: 5HPP-33 is an antiproliferative and antimitotic microtubule-stabilizer.
MedKoo Cat#: 561769
Name: 5HPP-33
CAS#: 105624-86-0
Chemical Formula: C20H21NO3
Exact Mass: 323.1521
Molecular Weight: 323.39
Elemental Analysis: C, 74.28; H, 6.55; N, 4.33; O, 14.84
Synonym: 5HPP-33; 5HPP 33; 5HPP33;
IUPAC/Chemical Name: 2-[2,6-Di(propan-2-yl)phenyl]-5-hydroxyisoindole-1,3-dione
InChi Key: LAKWINYVWJPHQW-UHFFFAOYSA-N
InChi Code: 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
SMILES Code: O=C1N(C2=C(C(C)C)C=CC=C2C(C)C)C(C3=C1C=CC(O)=C3)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 323.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
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.
