Synonym
TC-O 9311, TC-O-9311, TC-O9311, TCO 9311, TCO-9311, TCO9311
IUPAC/Chemical Name
3,5-dimethoxy-benzoic acid, 2-[(1-naphthalenylamino)carbonyl]hydrazide
InChi Key
KPTMSQHTGZMEFU-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H19N3O4/c1-26-15-10-14(11-16(12-15)27-2)19(24)22-23-20(25)21-18-9-5-7-13-6-3-4-8-17(13)18/h3-12H,1-2H3,(H,22,24)(H2,21,23,25)
SMILES Code
O=C(NNC(NC1=C2C=CC=CC2=CC=C1)=O)C3=CC(OC)=CC(OC)=C3
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
Biological target:
TC-O 9311 is a potent GPR139 agonist
In vivo activity:
A screening campaign identified compound 1a as a high potency GPR139 agonist with an EC50 = 39 nM in a calcium mobilization assay in CHO-K1 cells stably expressing the GPR139 receptor. In the absence of a known endogenous ligand, the maximum effect was set as 100% for 1a. Screening against 90 diverse targets revealed no cross-reactivity issues. Assessment of the pharmacokinetic properties showed limited utility as in vivo tool compound in rat with a poor whole brain exposure of 61 ng/g and a brain/plasma (b/p) ratio of 0.03. Attempts to identify a more suitable analogue identified the des-nitrogen analogue 1s with a reduced polar surface area of 76.7 Å(2) and an improved b/p ratio of 2.8. The whole brain exposure remained low at 95 ng/g due to a low plasma exposure.
Reference: Shi et al (2011) Discovery and SAR of a series of agonists at orphan G protein-coupled receptor 139. ACS Med.Chem.Lett. 2 303
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
14.0 |
38.32 |
| DMF |
11.0 |
30.10 |
| Ethanol |
14.0 |
38.32 |
| PBS (pH 7.2) |
5.0 |
13.68 |
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
365.39
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 |
Formulation protocol:
TBD
In vivo protocol:
Shi et al (2011) Discovery and SAR of a series of agonists at orphan G protein-coupled receptor 139. ACS Med.Chem.Lett. 2 303
Nepomuceno, D., Kuei, C., Dvorak, C., Lovenberg, T., Liu, C., & Bonaventure, P. (2018). Re-evaluation of adrenocorticotropic hormone and melanocyte stimulating hormone activation of GPR139 in vitro. Frontiers in Pharmacology, 9, 157.
Liu, C., Bonaventure, P., Lee, G., Nepomuceno, D., Kuei, C., Wu, J., ... & Lovenberg, T. W. (2015). GPR139, an orphan receptor highly enriched in the habenula and septum, is activated by the essential amino acids L-tryptophan and L-phenylalanine. Molecular Pharmacology, 88(5), 911-925.
