KRIBB3 is novel and potent microtubule inhibitor with potential anticancer activity. KRIBB3 has anti-migratory and anti-invasive activities in MDA-MB-231 cells. KRIBB3 inhibits tumor cell migration and invasion by blocking protein kinase C-dependent phosphorylation of Hsp27 through its direct binding to Hsp27.

MedKoo Cat#: 406512 Name: KRIBB3 CAS#: 129414-88-6 Chemical Formula: C19H19NO4 Exact Mass: 325.13141 Molecular Weight: 325.36 Elemental Analysis: C, 70.14; H, 5.89; N, 4.31; O, 19.67

Synonym: KRIBB3; KRIBB-3; KRIBB 3.

IUPAC/Chemical Name: 4-ethyl-5-methoxy-2-(4-(4-methoxyphenyl)isoxazol-5-yl)phenol

InChi Key: BNBHIGLOMVMJDB-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H19NO4/c1-4-12-9-15(17(21)10-18(12)23-3)19-16(11-20-24-19)13-5-7-14(22-2)8-6-13/h5-11,21H,4H2,1-3H3

SMILES Code: OC1=CC(OC)=C(CC)C=C1C2=C(C3=CC=C(OC)C=C3)C=NO2

Technical Data

Appearance: white 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, not in water

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).

Harmonized System Code: 293490

Additional Information

        

References

1: Qi S, Xin Y, Qi Z, Xu Y, Diao Y, Lan L, Luo L, Yin Z. HSP27 phosphorylation modulates TRAIL-induced activation of Src-Akt/ERK signaling through interaction with β-arrestin2. Cell Signal. 2014 Mar;26(3):594-602. doi: 10.1016/j.cellsig.2013.11.033. Epub 2013 Dec 2. PubMed PMID: 24308965.

2: Kaigorodova EV, Ryazantseva NV, Novitskii VV, Maroshkina AN, Belkina MV. Effects of HSP27 chaperone on THP-1 tumor cell apoptosis. Bull Exp Biol Med. 2012 Nov;154(1):77-9. PubMed PMID: 23330095.

3: Li J, Hu W, Lan Q. The apoptosis-resistance in t-AUCB-treated glioblastoma cells depends on activation of Hsp27. J Neurooncol. 2012 Nov;110(2):187-94. doi: 10.1007/s11060-012-0963-8. Epub 2012 Aug 18. PubMed PMID: 22903412.

4: Lee S, Kim JN, Lee HK, Yoon KS, Shin KD, Kwon BM, Han DC. Biological evaluation of KRIBB3 analogs as a microtubule polymerization inhibitor. Bioorg Med Chem Lett. 2011 Feb 1;21(3):977-9. doi: 10.1016/j.bmcl.2010.12.044. Epub 2010 Dec 13. PubMed PMID: 21215627.

5: Shin KD, Yoon YJ, Kang YR, Son KH, Kim HM, Kwon BM, Han DC. KRIBB3, a novel microtubule inhibitor, induces mitotic arrest and apoptosis in human cancer cells. Biochem Pharmacol. 2008 Jan 15;75(2):383-94. Epub 2007 Aug 30. PubMed PMID: 17915194.

6: Shin KD, Lee MY, Shin DS, Lee S, Son KH, Koh S, Paik YK, Kwon BM, Han DC. Blocking tumor cell migration and invasion with biphenyl isoxazole derivative KRIBB3, a synthetic molecule that inhibits Hsp27 phosphorylation. J Biol Chem. 2005 Dec 16;280(50):41439-48. Epub 2005 Oct 18. PubMed PMID: 16234246.