Synonym
EMD534085; EMD;534085; EMD 534085.
IUPAC/Chemical Name
1-(2-(dimethylamino)ethyl)-3-(((2R,4aS,5R,10bS)-5-phenyl-9-(trifluoromethyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-2-yl)methyl)urea
InChi Key
MARIUIDCPUZLKZ-FUKQBSRTSA-N
InChi Code
InChI=1S/C25H31F3N4O2/c1-32(2)13-12-29-24(33)30-15-18-9-10-19-22(16-6-4-3-5-7-16)31-21-11-8-17(25(26,27)28)14-20(21)23(19)34-18/h3-8,11,14,18-19,22-23,31H,9-10,12-13,15H2,1-2H3,(H2,29,30,33)/t18-,19+,22+,23+/m1/s1
SMILES Code
O=C(NC[C@H]1CC[C@@]2([H])[C@H](C3=CC=CC=C3)NC4=C(C=C(C(F)(F)F)C=C4)[C@@]2([H])O1)NCCN(C)C
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
>5 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
Biological target:
EMD534085 is a potent and selective inhibitor of the mitotic kinesin-5 with an IC50 of 8 nM.
In vivo activity:
The antitumor activity of EMD 534085 was determined in vivo using the subcutaneously growing human xenograft Colo205 colon carcinoma model. Two doses of EMD 534085 (15 mg/kg and 30 mg/kg) were applied twice weekly by ip injection when tumors reached a mean size of approximately 70 mm3. EMD 534085 caused a dose-dependent antitumor effect, which was resulting in a complete growth inhibition for the 30 mg/kg dose group (T/C = 19, p <0.001 Anova test) and in a reduced growth rate for the lower dose group (T/C = 62). Both doses of EMD 534085 were well tolerated as no body weight loss was observed (Fig. 3).
Reference: Bioorg Med Chem Lett. 2010 Mar 1;20(5):1491-5. https://pubmed.ncbi.nlm.nih.gov/20149654/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
26.0 |
54.56 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
476.53
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 |
Formulation protocol:
1. Schiemann K, Finsinger D, Zenke F, Amendt C, Knöchel T, Bruge D, Buchstaller HP, Emde U, Stähle W, Anzali S. The discovery and optimization of hexahydro-2H-pyrano[3,2-c]quinolines (HHPQs) as potent and selective inhibitors of the mitotic kinesin-5. Bioorg Med Chem Lett. 2010 Mar 1;20(5):1491-5. doi: 10.1016/j.bmcl.2010.01.110. Epub 2010 Jan 25. PMID: 20149654.
In vivo protocol:
1. Schiemann K, Finsinger D, Zenke F, Amendt C, Knöchel T, Bruge D, Buchstaller HP, Emde U, Stähle W, Anzali S. The discovery and optimization of hexahydro-2H-pyrano[3,2-c]quinolines (HHPQs) as potent and selective inhibitors of the mitotic kinesin-5. Bioorg Med Chem Lett. 2010 Mar 1;20(5):1491-5. doi: 10.1016/j.bmcl.2010.01.110. Epub 2010 Jan 25. PMID: 20149654.
1: Orth JD, Loewer A, Lahav G, Mitchison TJ. Prolonged mitotic arrest triggers partial activation of apoptosis, resulting in DNA damage and p53 induction. Mol Biol Cell. 2012 Feb;23(4):567-76. doi: 10.1091/mbc.E11-09-0781. Epub 2011 Dec 14. PubMed PMID: 22171325; PubMed Central PMCID: PMC3279386.
2: Tang Y, Orth JD, Xie T, Mitchison TJ. Rapid induction of apoptosis during Kinesin-5 inhibitor-induced mitotic arrest in HL60 cells. Cancer Lett. 2011 Nov 1;310(1):15-24. doi: 10.1016/j.canlet.2011.05.024. Epub 2011 Jun 24. PubMed PMID: 21782324; PubMed Central PMCID: PMC3155259.
3: Schiemann K, Finsinger D, Zenke F, Amendt C, Knöchel T, Bruge D, Buchstaller HP, Emde U, Stähle W, Anzali S. The discovery and optimization of hexahydro-2H-pyrano[3,2-c]quinolines (HHPQs) as potent and selective inhibitors of the mitotic kinesin-5. Bioorg Med Chem Lett. 2010 Mar 1;20(5):1491-5. doi: 10.1016/j.bmcl.2010.01.110. Epub 2010 Jan 25. PubMed PMID: 20149654.
