WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H522353
CAS#: 215802-15-6
Description: SB269652 is the first drug-like allosteric modulator of the dopamine D2 receptor (D2R). SB269652 binds in a bitopic manner at one protomer of a D2R dimer and modulates the binding of dopamine at a second protomer. Dr. Roberto Maggio's group at University of L'Aquila first domonstrated the allosteric nature of SB269652. This drug potently (low nanomolar range) abolished specific binding of [(3)H]nemanopride and [(3)H]spiperone to Chinese hamster ovary-transfected D(3) receptors when radioligands were used at 0.2 and 0.5 nM, respectively.
Hodoodo Cat#: H522353
Name: SB269652
CAS#: 215802-15-6
Chemical Formula: C27H30N4O
Exact Mass: 426.24
Molecular Weight: 426.560
Elemental Analysis: C, 76.03; H, 7.09; N, 13.13; O, 3.75
Synonym: SB269652; SB-269652; SB2 69652; SB269,652; SB-269,652; SB 269,652.
IUPAC/Chemical Name: N-((1r,4r)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-indole-2-carboxamide
InChi Key: JGLGOAQPUQITLD-OGAOHHHESA-N
InChi Code: InChI=1S/C27H30N4O/c28-17-20-5-8-21-12-14-31(18-23(21)15-20)13-11-19-6-9-24(10-7-19)29-27(32)26-16-22-3-1-2-4-25(22)30-26/h1-5,8,15-16,19,24,30H,6-7,9-14,18H2,(H,29,32)/t19-,24-
SMILES Code: O=C(C(N1)=CC2=C1C=CC=C2)N[C@H]3CC[C@H](CCN4CC5=C(C=CC(C#N)=C5)CC4)CC3
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, not in water
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:
| Biological target: | |
| In vitro activity: | |
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The following data is based on the product molecular weight 426.56 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Silvano E, Millan MJ, Mannoury la Cour C, Han Y, Duan L, Griffin SA, Luedtke RR, Aloisi G, Rossi M, Zazzeroni F, Javitch JA, Maggio R. The tetrahydroisoquinoline derivative SB269,652 is an allosteric antagonist at dopamine D3 and D2 receptors. Mol Pharmacol. 2010 Nov;78(5):925-34. doi: 10.1124/mol.110.065755. PubMed PMID: 20702763; PubMed Central PMCID: PMC2981362.
2: Kumar V, Moritz AE, Keck TM, Bonifazi A, Ellenberger MP, Sibley CD, Free RB, Shi L, Lane JR, Sibley DR, Newman AH. Synthesis and Pharmacological Characterization of Novel trans-Cyclopropylmethyl-Linked Bivalent Ligands That Exhibit Selectivity and Allosteric Pharmacology at the Dopamine D(3) Receptor (D(3)R). J Med Chem. 2017 Feb 23;60(4):1478-1494. doi: 10.1021/acs.jmedchem.6b01688. PubMed PMID: 28186762; PubMed Central PMCID: PMC5325712.
3: Maggio R, Scarselli M, Capannolo M, Millan MJ. Novel dimensions of D3 receptor function: Focus on heterodimerisation, transactivation and allosteric modulation. Eur Neuropsychopharmacol. 2015 Sep;25(9):1470-9. doi: 10.1016/j.euroneuro.2014.09.016. Review. PubMed PMID: 25453482.
4: Millan MJ, Seguin L, Gobert A, Cussac D, Brocco M. The role of dopamine D3 compared with D2 receptors in the control of locomotor activity: a combined behavioural and neurochemical analysis with novel, selective antagonists in rats. Psychopharmacology (Berl). 2004 Jul;174(3):341-57. PubMed PMID: 14985929.
5: Shonberg J, Draper-Joyce C, Mistry SN, Christopoulos A, Scammells PJ, Lane JR, Capuano B. Structure-activity study of N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-ind ole-2-carboxamide (SB269652), a bitopic ligand that acts as a negative allosteric modulator of the dopamine D2 receptor. J Med Chem. 2015 Jul 9;58(13):5287-307. doi: 10.1021/acs.jmedchem.5b00581. PubMed PMID: 26052807.
6: Mistry SN, Shonberg J, Draper-Joyce CJ, Klein Herenbrink C, Michino M, Shi L, Christopoulos A, Capuano B, Scammells PJ, Lane JR. Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D2 Receptor Through Fragmentation of a Bitopic Ligand. J Med Chem. 2015 Sep 10;58(17):6819-43. doi: 10.1021/acs.jmedchem.5b00585. PubMed PMID: 26258690.
