LUF 5834Potent adenosine A2A and A2B receptor partial agonist CAS# 333962-91-7 |
- HG-10-102-01
Catalog No.:BCC4271
CAS No.:1351758-81-0
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 333962-91-7 | SDF | Download SDF |
| PubChem ID | 10066330 | Appearance | Powder |
| Formula | C17H12N6OS | M.Wt | 348.38 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 100 mM in DMSO | ||
| Chemical Name | 2-amino-6-(1H-imidazol-2-ylmethylsulfanyl)-4-(4-oxocyclohexa-2,5-dien-1-ylidene)-1H-pyridine-3,5-dicarbonitrile | ||
| SMILES | C1=CC(=O)C=CC1=C2C(=C(NC(=C2C#N)SCC3=NC=CN3)N)C#N | ||
| Standard InChIKey | LOLJUQOCQBYBGT-UHFFFAOYSA-N | ||
| Standard InChI | 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/h1-6,23H,9,20H2,(H,21,22) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Potent A2A and A2B adenosine receptor partial agonist ( Ki = 2.6 nM and EC50 = 12 nM respectively). Also exhibits selectivity for A1 over A3 (Ki values are 2.6 and 538 nM respectively). |
LUF 5834 Dilution Calculator
LUF 5834 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.8704 mL | 14.3521 mL | 28.7043 mL | 57.4086 mL | 71.7607 mL |
| 5 mM | 0.5741 mL | 2.8704 mL | 5.7409 mL | 11.4817 mL | 14.3521 mL |
| 10 mM | 0.287 mL | 1.4352 mL | 2.8704 mL | 5.7409 mL | 7.1761 mL |
| 50 mM | 0.0574 mL | 0.287 mL | 0.5741 mL | 1.1482 mL | 1.4352 mL |
| 100 mM | 0.0287 mL | 0.1435 mL | 0.287 mL | 0.5741 mL | 0.7176 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
- Gartanin
Catalog No.:BCN5256
CAS No.:33390-42-0
- 8-Deoxygartanin
Catalog No.:BCN5255
CAS No.:33390-41-9
- Z-Asp(OtBu)-OSu
Catalog No.:BCC2787
CAS No.:3338-32-7
- 9-O-Methyl-4-hydroxyboeravinone B
Catalog No.:BCN4063
CAS No.:333798-10-0
- Theaflavine-3,3'-digallate
Catalog No.:BCN5420
CAS No.:33377-72-9
- Gliquidone
Catalog No.:BCC5003
CAS No.:33342-05-1
- Trianthenol
Catalog No.:BCN7802
CAS No.:333361-85-6
- NBD-556
Catalog No.:BCC1790
CAS No.:333353-44-9
- NBD-557
Catalog No.:BCC1791
CAS No.:333352-59-3
- Boc-Phe(4-NO2)-OH
Catalog No.:BCC3275
CAS No.:33305-77-0
- Dipsacoside B
Catalog No.:BCN5940
CAS No.:33289-85-9
- Gummiferin
Catalog No.:BCN8381
CAS No.:33286-30-5
- (E)-2-Decenoic acid
Catalog No.:BCC1292
CAS No.:334-49-6
- Spermidine trihydrochloride
Catalog No.:BCC6865
CAS No.:334-50-9
- 3-Hydroxy-3-acetonyloxindole
Catalog No.:BCN4069
CAS No.:33417-17-3
- Etoposide
Catalog No.:BCC1151
CAS No.:33419-42-0
- Quercetin 3,4'-dimethyl ether
Catalog No.:BCN5257
CAS No.:33429-83-3
- 2-Pyridylethylamine dihydrochloride
Catalog No.:BCC7379
CAS No.:3343-39-3
- 3,3'-Bilawsone
Catalog No.:BCN7912
CAS No.:33440-64-1
- Alnustone
Catalog No.:BCN2761
CAS No.:33457-62-4
- Evonine
Catalog No.:BCN3087
CAS No.:33458-82-1
- AH 6809
Catalog No.:BCC1332
CAS No.:33458-93-4
- 3-Aminopiperidine dihydrochloride
Catalog No.:BCC8619
CAS No.:334618-23-4
- Tracheloside
Catalog No.:BCN2738
CAS No.:33464-71-0
A novel nonribose agonist, LUF5834, engages residues that are distinct from those of adenosine-like ligands to activate the adenosine A(2a) receptor.[Pubmed:22188926]
Mol Pharmacol. 2012 Mar;81(3):475-87.
The recent publication of both the antagonist- and agonist-bound structures of the adenosine A(2A) receptor have revealed much about how a ligand may bind to a receptor and cause the conformational changes associated with agonist-mediated activation. In particular, the agonist-bound structure revealed key interactions between the ribose group of adenosine-derived agonists and amino acids in the receptor binding pocket that lead to receptor activation. However, agonists without a ribose group also exist, and we wondered whether such compounds occupy the same agonist binding site. Therefore we used a mutagenesis approach in this study to investigate the mode of binding of 2-amino-4-(4-hydroxyphenyl)- 6-(1H-imidazol-2-ylmethylsulfanyl)pyridine-3,5-dicarbonitrile (LUF5834), a potent partial agonist without a ribose moiety, compared with the adenosine-derived reference agonist 2-[p-(2-carboxyethyl)phenyl-ethylamino]-5'-N-ethylcarboxamidoadenosine (CGS21680). Mutation of the orthosteric residue Phe168 to alanine abrogated the function of both agonists. However, mutation to alanine of residues Thr88 and Ser277 shown by the crystal structures to interact with the ribose group of adenosine-like ligands had no effect on the potency of LUF5834. Furthermore, alanine mutation of Asn253, which makes a hydrogen-bonding interaction with the exocyclic nitrogen of the adenine ring, had minimal effect on LUF5834 affinity but removed agonist activity of this ligand. Mutation of other residues, such as the highly conserved Trp246 or Glu13, had significant deleterious effects on the function of CGS21680 but little effect on LUF5834. In summary, our findings suggest that this class of agonist interacts with distinct residues to activate the receptor compared with classic adenosine derived agonists.
New, non-adenosine, high-potency agonists for the human adenosine A2B receptor with an improved selectivity profile compared to the reference agonist N-ethylcarboxamidoadenosine.[Pubmed:15239649]
J Med Chem. 2004 Jul 15;47(15):3707-9.
The adenosine A(2B) receptor is the least well characterized of the four known adenosine receptor subtypes because of the absence of potent, selective agonists. Here, we present five non-adenosine agonists. Among them, 2-amino-4-(4-hydroxyphenyl)-6-(1H-imidazol-2-ylmethylsulfanyl)pyridine-3,5-dicarb onitrile, 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. Compound 18, LUF5835, the 3-hydroxyphenyl analogue, is a full agonist with EC(50) = 10 nM.
