Synonym
HR22C16; HR-22-C-16; HR 22 C 16;
IUPAC/Chemical Name
2-butyl-5-(3-hydroxyphenyl)-5,6,11,11a-tetrahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indole-1,3(2H)-dione
InChi Key
IDGCPAFIELNTPI-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H23N3O3/c1-2-3-11-25-22(28)19-13-17-16-9-4-5-10-18(16)24-20(17)21(26(19)23(25)29)14-7-6-8-15(27)12-14/h4-10,12,19,21,24,27H,2-3,11,13H2,1H3
SMILES Code
O=C(C1CC2=C(C(C3=CC=CC(O)=C3)N14)NC5=C2C=CC=C5)N(CCCC)C4=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
389.45
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: Shankaraiah N, Nekkanti S, Chudasama KJ, Senwar KR, Sharma P, Jeengar MK, Naidu VG, Srinivasulu V, Srinivasulu G, Kamal A. Design, synthesis and anticancer evaluation of tetrahydro-β-carboline-hydantoin hybrids. Bioorg Med Chem Lett. 2014 Dec 1;24(23):5413-7. PubMed PMID: 25453799.
2: Liu F, Yu LQ, Jiang C, Yang L, Wu WT, You QD. Discovery of tetrahydro-beta-carbolines as inhibitors of the mitotic kinesin KSP. Bioorg Med Chem. 2010 Jun 15;18(12):4167-77. doi: 10.1016/j.bmc.2010.05.024. Epub 2010 May 11. PubMed PMID: 20537544.
3: Jiang C, Chen Y, Wang X, You Q. Docking studies on kinesin spindle protein inhibitors: an important cooperative 'minor binding pocket' which increases the binding affinity significantly. J Mol Model. 2007 Sep;13(9):987-92. Epub 2007 Jun 23. PubMed PMID: 17588180.
4: Dastidar PG, Majumder S, Lohia A. Eh Klp5 is a divergent member of the kinesin 5 family that regulates genome content and microtubular assembly in Entamoeba histolytica. Cell Microbiol. 2007 Feb;9(2):316-28. Epub 2006 Aug 22. PubMed PMID: 16925786.
5: Sunder-Plassmann N, Sarli V, Gartner M, Utz M, Seiler J, Huemmer S, Mayer TU, Surrey T, Giannis A. Synthesis and biological evaluation of new tetrahydro-beta-carbolines as inhibitors of the mitotic kinesin Eg5. Bioorg Med Chem. 2005 Nov 15;13(22):6094-111. Epub 2005 Aug 3. PubMed PMID: 16084101.
6: Marcus AI, Peters U, Thomas SL, Garrett S, Zelnak A, Kapoor TM, Giannakakou P. Mitotic kinesin inhibitors induce mitotic arrest and cell death in Taxol-resistant and -sensitive cancer cells. J Biol Chem. 2005 Mar 25;280(12):11569-77. Epub 2005 Jan 13. PubMed PMID: 15653676; PubMed Central PMCID: PMC1861807.
7: Hotha S, Yarrow JC, Yang JG, Garrett S, Renduchintala KV, Mayer TU, Kapoor TM. HR22C16: a potent small-molecule probe for the dynamics of cell division. Angew Chem Int Ed Engl. 2003 May 30;42(21):2379-82. PubMed PMID: 12783501.
