KCC009

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 407381

CAS#: 744198-19-4

Description: KCC009 is a potent and selective Transglutaminase 2 Inhibitor. KCC009 exhibits potent radiosensitization effects in human lung cancer cells expressing wild-type or mutant p53 with different mechanisms. KCC009 disrupts fibronectin assembly in the extracellular matrix and sensitizes orthotopic glioblastomas to chemotherapy. KCC009 decreased DDC-induced liver enlargement without affecting MB formation or extent of liver injury. KCC-009 significantly attenuated the damaging effects of warfarin on arterial tissue.


Chemical Structure

img
KCC009
CAS# 744198-19-4

Theoretical Analysis

MedKoo Cat#: 407381
Name: KCC009
CAS#: 744198-19-4
Chemical Formula: C21H22BrN3O5
Exact Mass: 475.07
Molecular Weight: 476.327
Elemental Analysis: C, 52.95; H, 4.66; Br, 16.78; N, 8.82; O, 16.79

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Related CAS #: 120244-89-5 (R-isomer)   744198-19-4 (KCC009)  

Synonym: KCC009; KCC-009; KCC 009.

IUPAC/Chemical Name: benzyl ((2S)-1-(((3-bromo-4,5-dihydroisoxazol-5-yl)methyl)amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamate

InChi Key: MRULUIQNANUWTK-ZVAWYAOSSA-N

InChi Code: InChI=1S/C21H22BrN3O5/c22-19-11-17(30-25-19)12-23-20(27)18(10-14-6-8-16(26)9-7-14)24-21(28)29-13-15-4-2-1-3-5-15/h1-9,17-18,26H,10-13H2,(H,23,27)(H,24,28)/t17?,18-/m0/s1

SMILES Code: O=C(OCC1=CC=CC=C1)N[C@@H](CC2=CC=C(O)C=C2)C(NCC3CC(Br)=NO3)=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

More Info: KCC009 S-isomer has CAS#120244-89-5 also called ERW 1095A, or RS 10823

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 476.33 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Huaying S, Dong Y, Chihong Z, Xiaoqian Q, Danying W, Jianguo F. Transglutaminase 2 Inhibitor KCC009 Induces p53-Independent Radiosensitization in Lung Adenocarcinoma Cells. Med Sci Monit. 2016 Dec 21;22:5041-5048. PubMed PMID: 28002389; PubMed Central PMCID: PMC5198751.

2: Yuan L, Siegel M, Choi K, Khosla C, Miller CR, Jackson EN, Piwnica-Worms D, Rich KM. Transglutaminase 2 inhibitor, KCC009, disrupts fibronectin assembly in the extracellular matrix and sensitizes orthotopic glioblastomas to chemotherapy. Oncogene. 2007 Apr 19;26(18):2563-73. PubMed PMID: 17099729.

3: Strnad P, Siegel M, Toivola DM, Choi K, Kosek JC, Khosla C, Omary MB. Pharmacologic transglutaminase inhibition attenuates drug-primed liver hypertrophy but not Mallory body formation. FEBS Lett. 2006 Apr 17;580(9):2351--2357. PubMed PMID: 16616523.

4: Konoplyannikov M, Nurminskaya M. New therapeutic approaches to arterial calcification via inhibition of transglutaminase and β-catenin signaling. Curr Pharm Des. 2014;20(37):5811-20. Review. PubMed PMID: 24533936.

5: Beazley KE, Banyard D, Lima F, Deasey SC, Nurminsky DI, Konoplyannikov M, Nurminskaya MV. Transglutaminase inhibitors attenuate vascular calcification in a preclinical model. Arterioscler Thromb Vasc Biol. 2013 Jan;33(1):43-51. doi: 10.1161/ATVBAHA.112.300260. PubMed PMID: 23117658; PubMed Central PMCID: PMC3544469.

6: Frese-Schaper M, Schardt JA, Sakai T, Carboni GL, Schmid RA, Frese S. Inhibition of tissue transglutaminase sensitizes TRAIL-resistant lung cancer cells through upregulation of death receptor 5. FEBS Lett. 2010 Jul 2;584(13):2867-71. doi: 10.1016/j.febslet.2010.04.072. PubMed PMID: 20450916.

7: Yuan L, Behdad A, Siegel M, Khosla C, Higashikubo R, Rich KM. Tissue transgluaminase 2 expression in meningiomas. J Neurooncol. 2008 Nov;90(2):125-32. doi: 10.1007/s11060-008-9642-1. PubMed PMID: 18587533; PubMed Central PMCID: PMC3732188.

8: Cao L, Petrusca DN, Satpathy M, Nakshatri H, Petrache I, Matei D. Tissue transglutaminase protects epithelial ovarian cancer cells from cisplatin-induced apoptosis by promoting cell survival signaling. Carcinogenesis. 2008 Oct;29(10):1893-900. doi: 10.1093/carcin/bgn158. PubMed PMID: 18667446; PubMed Central PMCID: PMC2556973.

9: Yuan L, Holmes TC, Watts RE, Khosla C, Broekelmann TJ, Mecham R, Zheng H, Izaguirre EW, Rich KM. Novel chemo-sensitizing agent, ERW1227B, impairs cellular motility and enhances cell death in glioblastomas. J Neurooncol. 2011 Jun;103(2):207-19. doi: 10.1007/s11060-010-0379-2. PubMed PMID: 20824305; PubMed Central PMCID: PMC3732656.

10: Deasey S, Grichenko O, Du S, Nurminskaya M. Characterization of the transglutaminase gene family in zebrafish and in vivo analysis of transglutaminase-dependent bone mineralization. Amino Acids. 2012 Feb;42(2-3):1065-75. doi: 10.1007/s00726-011-1021-0. PubMed PMID: 21809079; PubMed Central PMCID: PMC3266987.

11: Deasey S, Shanmugasundaram S, Nurminskaya M. Tissue-specific responses to loss of transglutaminase 2. Amino Acids. 2013 Jan;44(1):179-87. doi: 10.1007/s00726-011-1183-9. PubMed PMID: 22194042; PubMed Central PMCID: PMC3536932.

12: Verhaar R, Jongenelen CA, Gerard M, Baekelandt V, Van Dam AM, Wilhelmus MM, Drukarch B. Blockade of enzyme activity inhibits tissue transglutaminase-mediated transamidation of α-synuclein in a cellular model of Parkinson's disease. Neurochem Int. 2011 Jun;58(7):785-93. doi: 10.1016/j.neuint.2011.03.004. PubMed PMID: 21440023.

13: van Strien ME, de Vries HE, Chrobok NL, Bol JG, Breve JJ, van der Pol SM, Kooij G, van Buul JD, Karpuj M, Steinman L, Wilhelmus MM, Sestito C, Drukarch B, Van Dam AM. Tissue Transglutaminase contributes to experimental multiple sclerosis pathogenesis and clinical outcome by promoting macrophage migration. Brain Behav Immun. 2015 Nov;50:141-54. doi: 10.1016/j.bbi.2015.06.023. PubMed PMID: 26133787.

14: Matic I, Sacchi A, Rinaldi A, Melino G, Khosla C, Falasca L, Piacentini M. Characterization of transglutaminase type II role in dendritic cell differentiation and function. J Leukoc Biol. 2010 Jul;88(1):181-8. doi: 10.1189/jlb.1009691. PubMed PMID: 20371597; PubMed Central PMCID: PMC3210574.

15: Lee JH, Jeong J, Jeong EM, Cho SY, Kang JW, Lim J, Heo J, Kang H, Kim IG, Shin DM. Endoplasmic reticulum stress activates transglutaminase 2 leading to protein aggregation. Int J Mol Med. 2014 Apr;33(4):849-55. doi: 10.3892/ijmm.2014.1640. PubMed PMID: 24481335; PubMed Central PMCID: PMC3976127.

16: Satpathy M, Shao M, Emerson R, Donner DB, Matei D. Tissue transglutaminase regulates matrix metalloproteinase-2 in ovarian cancer by modulating cAMP-response element-binding protein activity. J Biol Chem. 2009 Jun 5;284(23):15390-9. doi: 10.1074/jbc.M808331200. PubMed PMID: 19324884; PubMed Central PMCID: PMC2708835.

17: Yuan L, Choi K, Khosla C, Zheng X, Higashikubo R, Chicoine MR, Rich KM. Tissue transglutaminase 2 inhibition promotes cell death and chemosensitivity in glioblastomas. Mol Cancer Ther. 2005 Sep;4(9):1293-302. PubMed PMID: 16170020.