Synonym
LUF6000; LUF 6000; LUF-6000.
IUPAC/Chemical Name
2-cyclohexyl-N-(3,4-dichlorophenyl)-3H-imidazo[4,5-c]quinolin-4-amine
InChi Key
UWJVRSIGHHSDSJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H20Cl2N4/c23-16-11-10-14(12-17(16)24)25-22-20-19(15-8-4-5-9-18(15)26-22)27-21(28-20)13-6-2-1-3-7-13/h4-5,8-13H,1-3,6-7H2,(H,25,26)(H,27,28)
SMILES Code
ClC1=CC=C(NC2=NC3=CC=CC=C3C4=C2NC(C5CCCCC5)=N4)C=C1Cl
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:
LUF6000 is an orally active allosteric modulator of the A3 adenosine receptor.
In vitro activity:
Most prominently, compound 43 (LUF6000) was found to enhance agonist efficacy in a functional assay by 45% and decrease dissociation rate similarly without influencing agonist potency.
Reference: J Med Chem. 2006 Jun 1;49(11):3354-61. https://pubmed.ncbi.nlm.nih.gov/16722654/
In vivo activity:
LUF6000 administration induced anti-inflammatory effect in 3 experimental animal models of rat adjuvant induced arthritis, monoiodoacetate induced osteoarthritis, and concanavalin A induced liver inflammation in mice.
Reference: Mediators Inflamm. 2014;2014:708746. https://pubmed.ncbi.nlm.nih.gov/25374446/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
14.3 |
34.74 |
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
411.33
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. Gao ZG, Verzijl D, Zweemer A, Ye K, Göblyös A, Ijzerman AP, Jacobson KA. Functionally biased modulation of A(3) adenosine receptor agonist efficacy and potency by imidazoquinolinamine allosteric enhancers. Biochem Pharmacol. 2011 Sep 15;82(6):658-68. doi: 10.1016/j.bcp.2011.06.017. Epub 2011 Jun 21. PMID: 21718691; PMCID: PMC3152598.
2. Göblyös A, Gao ZG, Brussee J, Connestari R, Santiago SN, Ye K, Ijzerman AP, Jacobson KA. Structure-activity relationships of new 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric enhancers of the A3 adenosine receptor. J Med Chem. 2006 Jun 1;49(11):3354-61. doi: 10.1021/jm060086s. PMID: 16722654; PMCID: PMC2547348.
3. Cohen S, Barer F, Bar-Yehuda S, IJzerman AP, Jacobson KA, Fishman P. A₃ adenosine receptor allosteric modulator induces an anti-inflammatory effect: in vivo studies and molecular mechanism of action. Mediators Inflamm. 2014;2014:708746. doi: 10.1155/2014/708746. Epub 2014 Oct 13. PMID: 25374446; PMCID: PMC4211160.
In vitro protocol:
1. Gao ZG, Verzijl D, Zweemer A, Ye K, Göblyös A, Ijzerman AP, Jacobson KA. Functionally biased modulation of A(3) adenosine receptor agonist efficacy and potency by imidazoquinolinamine allosteric enhancers. Biochem Pharmacol. 2011 Sep 15;82(6):658-68. doi: 10.1016/j.bcp.2011.06.017. Epub 2011 Jun 21. PMID: 21718691; PMCID: PMC3152598.
2. Göblyös A, Gao ZG, Brussee J, Connestari R, Santiago SN, Ye K, Ijzerman AP, Jacobson KA. Structure-activity relationships of new 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric enhancers of the A3 adenosine receptor. J Med Chem. 2006 Jun 1;49(11):3354-61. doi: 10.1021/jm060086s. PMID: 16722654; PMCID: PMC2547348.
In vivo protocol:
1. Cohen S, Barer F, Bar-Yehuda S, IJzerman AP, Jacobson KA, Fishman P. A₃ adenosine receptor allosteric modulator induces an anti-inflammatory effect: in vivo studies and molecular mechanism of action. Mediators Inflamm. 2014;2014:708746. doi: 10.1155/2014/708746. Epub 2014 Oct 13. PMID: 25374446; PMCID: PMC4211160.
1: Jacobson KA, Müller CE. Medicinal chemistry of adenosine, P2Y and P2X receptors. Neuropharmacology. 2016 May;104:31-49. doi: 10.1016/j.neuropharm.2015.12.001. Epub 2015 Dec 12. Review. PubMed PMID: 26686393; PubMed Central PMCID: PMC4871727.
2: Deganutti G, Cuzzolin A, Ciancetta A, Moro S. Understanding allosteric interactions in G protein-coupled receptors using Supervised Molecular Dynamics: A prototype study analysing the human A3 adenosine receptor positive allosteric modulator LUF6000. Bioorg Med Chem. 2015 Jul 15;23(14):4065-71. doi: 10.1016/j.bmc.2015.03.039. Epub 2015 Mar 20. PubMed PMID: 25868747.
3: Cohen S, Barer F, Bar-Yehuda S, IJzerman AP, Jacobson KA, Fishman P. A₃ adenosine receptor allosteric modulator induces an anti-inflammatory effect: in vivo studies and molecular mechanism of action. Mediators Inflamm. 2014;2014:708746. doi: 10.1155/2014/708746. Epub 2014 Oct 13. PubMed PMID: 25374446; PubMed Central PMCID: PMC4211160.
4: Gao ZG, Verzijl D, Zweemer A, Ye K, Göblyös A, Ijzerman AP, Jacobson KA. Functionally biased modulation of A(3) adenosine receptor agonist efficacy and potency by imidazoquinolinamine allosteric enhancers. Biochem Pharmacol. 2011 Sep 15;82(6):658-68. doi: 10.1016/j.bcp.2011.06.017. Epub 2011 Jun 21. PubMed PMID: 21718691; PubMed Central PMCID: PMC3152598.
5: Szentmiklósi AJ, Cseppento A, Harmati G, Nánási PP. Novel trends in the treatment of cardiovascular disorders: site- and event- selective adenosinergic drugs. Curr Med Chem. 2011;18(8):1164-87. Review. PubMed PMID: 21291368.
6: Heitman LH, Göblyös A, Zweemer AM, Bakker R, Mulder-Krieger T, van Veldhoven JP, de Vries H, Brussee J, Ijzerman AP. A series of 2,4-disubstituted quinolines as a new class of allosteric enhancers of the adenosine A3 receptor. J Med Chem. 2009 Feb 26;52(4):926-31. doi: 10.1021/jm8014052. PubMed PMID: 19161279.
7: Gao ZG, Ye K, Göblyös A, Ijzerman AP, Jacobson KA. Flexible modulation of agonist efficacy at the human A3 adenosine receptor by the imidazoquinoline allosteric enhancer LUF6000. BMC Pharmacol. 2008 Dec 12;8:20. doi: 10.1186/1471-2210-8-20. PubMed PMID: 19077268; PubMed Central PMCID: PMC2625337.
8: Göblyös A, Gao ZG, Brussee J, Connestari R, Santiago SN, Ye K, Ijzerman AP, Jacobson KA. Structure-activity relationships of new 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric enhancers of the A3 adenosine receptor. J Med Chem. 2006 Jun 1;49(11):3354-61. PubMed PMID: 16722654; PubMed Central PMCID: PMC2547348.
