Synonym
LUF5834; LUF-5834; LUF 5834;
IUPAC/Chemical Name
2-Amino-4-(4-hydroxyphenyl)- 6-(1H-imidazol-2-ylmethylsulfanyl)pyridine-3,5-dicarbonitrile
InChi Key
OFHKDLYFKPBXER-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H12N6OS/c18-7-12-15(10-1-3-11(24)4-2-10)13(8-19)17(23-16(12)20)25-9-14-21-5-6-22-14/h1-6,24H,9H2,(H2,20,23)(H,21,22)
SMILES Code
N#CC1=C(C2=CC=C(O)C=C2)C(C#N)=C(SCC3=NC=CN3)N=C1N
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:
LUF5834 is a potent nonribose agonist, activating A2A and A2B adenosine receptor.
In vitro activity:
Among them, 2-amino-4-(4-hydroxyphenyl)-6-(1H-imidazol-2-ylmethylsulfanyl)pyridine-3,5-dicarbonitrile, 17, LUF5834, is a high-efficacy partial agonist with EC(50) = 12 nM and 45-fold selectivity over the adenosine A(3) receptor but lacking selectivity versus the A(1) and A(2A) subtypes.
Reference: J Med Chem. 2004 Jul 15;47(15):3707-9. https://pubmed.ncbi.nlm.nih.gov/15239649/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
34.8 |
100.00 |
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
348.38
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. Lane JR, Klaasse E, Lin J, van Bruchem J, Beukers MW, Ijzerman AP. Characterization of [3H]LUF5834: A novel non-ribose high-affinity agonist radioligand for the adenosine A1 receptor. Biochem Pharmacol. 2010 Oct 15;80(8):1180-9. doi: 10.1016/j.bcp.2010.06.041. Epub 2010 Jun 30. PMID: 20599769.
2. Beukers MW, Chang LC, von Frijtag Drabbe Künzel JK, Mulder-Krieger T, Spanjersberg RF, Brussee J, IJzerman AP. New, non-adenosine, high-potency agonists for the human adenosine A2B receptor with an improved selectivity profile compared to the reference agonist N-ethylcarboxamidoadenosine. J Med Chem. 2004 Jul 15;47(15):3707-9. doi: 10.1021/jm049947s. PMID: 15239649.
In vitro protocol:
1. Lane JR, Klaasse E, Lin J, van Bruchem J, Beukers MW, Ijzerman AP. Characterization of [3H]LUF5834: A novel non-ribose high-affinity agonist radioligand for the adenosine A1 receptor. Biochem Pharmacol. 2010 Oct 15;80(8):1180-9. doi: 10.1016/j.bcp.2010.06.041. Epub 2010 Jun 30. PMID: 20599769.
2. Beukers MW, Chang LC, von Frijtag Drabbe Künzel JK, Mulder-Krieger T, Spanjersberg RF, Brussee J, IJzerman AP. New, non-adenosine, high-potency agonists for the human adenosine A2B receptor with an improved selectivity profile compared to the reference agonist N-ethylcarboxamidoadenosine. J Med Chem. 2004 Jul 15;47(15):3707-9. doi: 10.1021/jm049947s. PMID: 15239649.
1: Noël F, do Monte FM. Validation of a Na(+)-shift binding assay for estimation of the intrinsic efficacy of ligands at the A(2A) adenosine receptor. J Pharmacol Toxicol Methods. 2017 Mar - Apr;84:51-56. doi: 10.1016/j.vascn.2016.10.009. Epub 2016 Nov 1. PubMed PMID: 27810394.
2: Ye L, Van Eps N, Zimmer M, Ernst OP, Prosser RS. Activation of the A2A adenosine G-protein-coupled receptor by conformational selection. Nature. 2016 May 12;533(7602):265-8. doi: 10.1038/nature17668. Epub 2016 May 4. PubMed PMID: 27144352.
3: Lane JR, Klein Herenbrink C, van Westen GJ, Spoorendonk JA, Hoffmann C, IJzerman AP. A novel nonribose agonist, LUF5834, engages residues that are distinct from those of adenosine-like ligands to activate the adenosine A(2a) receptor. Mol Pharmacol. 2012 Mar;81(3):475-87. doi: 10.1124/mol.111.075937. Epub 2011 Dec 21. PubMed PMID: 22188926.
4: Lane JR, Klaasse E, Lin J, van Bruchem J, Beukers MW, Ijzerman AP. Characterization of [3H]LUF5834: A novel non-ribose high-affinity agonist radioligand for the adenosine A1 receptor. Biochem Pharmacol. 2010 Oct 15;80(8):1180-9. doi: 10.1016/j.bcp.2010.06.041. Epub 2010 Jun 30. PubMed PMID: 20599769.
5: Urmaliya VB, Church JE, Coupar IM, Rose'Meyer RB, Pouton CW, White PJ. Cardioprotection induced by adenosine A1 receptor agonists in a cardiac cell ischemia model involves cooperative activation of adenosine A2A and A2B receptors by endogenous adenosine. J Cardiovasc Pharmacol. 2009 May;53(5):424-33. doi: 10.1097/FJC.0b013e3181a443e2. PubMed PMID: 19333129.
6: Beukers MW, Chang LC, von Frijtag Drabbe Künzel JK, Mulder-Krieger T, Spanjersberg RF, Brussee J, IJzerman AP. New, non-adenosine, high-potency agonists for the human adenosine A2B receptor with an improved selectivity profile compared to the reference agonist N-ethylcarboxamidoadenosine. J Med Chem. 2004 Jul 15;47(15):3707-9. PubMed PMID: 15239649.
