Synonym
ML-193; ML 193; ML193; CID 1261822; CID-1261822; CID1261822.
IUPAC/Chemical Name
N-[4-[[(3,4-Dimethyl-5-isoxazolyl)amino]sulfonyl]phenyl]-6,8-dimethyl-2-(2-pyridinyl)-4-quinolinecarboxamide
InChi Key
HTSLEZOTMYUPLU-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H25N5O4S/c1-16-13-17(2)26-22(14-16)23(15-25(31-26)24-7-5-6-12-29-24)27(34)30-20-8-10-21(11-9-20)38(35,36)33-28-18(3)19(4)32-37-28/h5-15,33H,1-4H3,(H,30,34)
SMILES Code
O=C(C1=CC(C2=NC=CC=C2)=NC3=C(C)C=C(C)C=C13)NC4=CC=C(S(=O)(NC5=C(C)C(C)=NO5)=O)C=C4
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:
ML-193 (CID 1261822) is a potent and selective antagonist of GPR55, with an IC50 of 221 nM.
In vitro activity:
The effects of GPR55 agonists (LPI, O-1602, ML184) on human (h) NSC (neural stem cell) proliferation in vitro were assessed by flow cytometry. Activation of GPR55 significantly increased proliferation rates of hNSCs in vitro. These effects were attenuated by ML193, a selective GPR55 antagonist. ML184 significantly promoted neuronal differentiation in vitro while ML193 reduced differentiation rates as compared to vehicle treatment.
Reference: Br J Pharmacol. 2018 Aug;175(16):3407-3421. https://pubmed.ncbi.nlm.nih.gov/29888782/
In vivo activity:
Experimental Parkinson was induced by unilateral intra-striatal administration of 6-hydroxydopamine (6-OHDA, 10 µg/rat). L-α-lysophosphatidylinositol (LPI, 1 and 5 µg/rat), an endogenous GPR55 agonist, and ML193 (1 and 5 µg/rat), a selective GPR55 antagonist, were injected into the striatum of 6-OHDA-lesioned rats. Intra-striatal administration of ML193 also increased time on the rotarod, decreased latency to remove the label and slip steps in 6-OHDA-lesioned rats mostly at the dose of 1 µg/rat.
Reference: Acta Neuropsychiatr. 2021 Feb;33(1):15-21. https://pubmed.ncbi.nlm.nih.gov/32967746/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
52.8 |
100.00 |
|
| DMF |
3.0 |
5.69 |
|
| DMF:PBS (pH 7.2) (1:4) |
0.2 |
0.38 |
|
| Ethanol |
0.1 |
0.19 |
|
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
527.60
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. Hill JD, Zuluaga-Ramirez V, Gajghate S, Winfield M, Persidsky Y. Activation of GPR55 increases neural stem cell proliferation and promotes early adult hippocampal neurogenesis. Br J Pharmacol. 2018 Aug;175(16):3407-3421. doi: 10.1111/bph.14387. Epub 2018 Jul 4. PMID: 29888782; PMCID: PMC6057896.
2. Deliu E, Sperow M, Console-Bram L, Carter RL, Tilley DG, Kalamarides DJ, Kirby LG, Brailoiu GC, Brailoiu E, Benamar K, Abood ME. The Lysophosphatidylinositol Receptor GPR55 Modulates Pain Perception in the Periaqueductal Gray. Mol Pharmacol. 2015 Aug;88(2):265-72. doi: 10.1124/mol.115.099333. Epub 2015 May 13. PMID: 25972448; PMCID: PMC4518086.
3. Fatemi I, Abdollahi A, Shamsizadeh A, Allahtavakoli M, Roohbakhsh A. The effect of intra-striatal administration of GPR55 agonist (LPI) and antagonist (ML193) on sensorimotor and motor functions in a Parkinson's disease rat model. Acta Neuropsychiatr. 2021 Feb;33(1):15-21. doi: 10.1017/neu.2020.30. Epub 2020 Sep 24. PMID: 32967746.
4. Rahimi A, Hajizadeh Moghaddam A, Roohbakhsh A. Central administration of GPR55 receptor agonist and antagonist modulates anxiety-related behaviors in rats. Fundam Clin Pharmacol. 2015 Apr;29(2):185-90. doi: 10.1111/fcp.12099. Epub 2015 Mar 11. PMID: 25620584.
In vitro protocol:
1. Hill JD, Zuluaga-Ramirez V, Gajghate S, Winfield M, Persidsky Y. Activation of GPR55 increases neural stem cell proliferation and promotes early adult hippocampal neurogenesis. Br J Pharmacol. 2018 Aug;175(16):3407-3421. doi: 10.1111/bph.14387. Epub 2018 Jul 4. PMID: 29888782; PMCID: PMC6057896.
2. Deliu E, Sperow M, Console-Bram L, Carter RL, Tilley DG, Kalamarides DJ, Kirby LG, Brailoiu GC, Brailoiu E, Benamar K, Abood ME. The Lysophosphatidylinositol Receptor GPR55 Modulates Pain Perception in the Periaqueductal Gray. Mol Pharmacol. 2015 Aug;88(2):265-72. doi: 10.1124/mol.115.099333. Epub 2015 May 13. PMID: 25972448; PMCID: PMC4518086.
In vivo protocol:
1. Fatemi I, Abdollahi A, Shamsizadeh A, Allahtavakoli M, Roohbakhsh A. The effect of intra-striatal administration of GPR55 agonist (LPI) and antagonist (ML193) on sensorimotor and motor functions in a Parkinson's disease rat model. Acta Neuropsychiatr. 2021 Feb;33(1):15-21. doi: 10.1017/neu.2020.30. Epub 2020 Sep 24. PMID: 32967746.
2. Rahimi A, Hajizadeh Moghaddam A, Roohbakhsh A. Central administration of GPR55 receptor agonist and antagonist modulates anxiety-related behaviors in rats. Fundam Clin Pharmacol. 2015 Apr;29(2):185-90. doi: 10.1111/fcp.12099. Epub 2015 Mar 11. PMID: 25620584.
1: Leo LM, Familusi B, Hoang M, Smith R, Lindenau K, Sporici KT, Brailoiu E, Abood ME, Brailoiu GC. GPR55-mediated effects on brain microvascular endothelial cells and the blood-brain barrier. Neuroscience. 2019 Aug 21;414:88-98. doi: 10.1016/j.neuroscience.2019.06.039. Epub 2019 Jul 4. PMID: 31279825; PMCID: PMC6684354.
2: Deliu E, Sperow M, Console-Bram L, Carter RL, Tilley DG, Kalamarides DJ, Kirby LG, Brailoiu GC, Brailoiu E, Benamar K, Abood ME. The Lysophosphatidylinositol Receptor GPR55 Modulates Pain Perception in the Periaqueductal Gray. Mol Pharmacol. 2015 Aug;88(2):265-72. doi: 10.1124/mol.115.099333. Epub 2015 May 13. PMID: 25972448; PMCID: PMC4518086..
