LUF 6000 - CAS 890087-21-5
Catalog number:
890087-21-5
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C22H20Cl2N4
Molecular Weight:
411.33
COA:
Inquire
Targets:
Adenosine Receptor
Description:
LUF6000 is an allosteric modulator of the human A3 adenosine receptor (AR). It was found to be an allosteric enhancer of Emax. It exerted an Emax-enhancing effect at a concentration of 0.1 microM or higher. It was shown to increase the Emax of Cl-IB-MECA and other low-efficacy agonists to a larger extent than that of the high-efficacy agonist NECA. It converted a nucleoside A3 AR antagonist MRS542. It has anti-inflammatory effect.
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Purity:
>98 %
Appearance:
Solid powder
Synonyms:
LUF-6000;N-(3,4-Dichlorophenyl)-2-cyclohexyl-1H-imidazo[4,5-c]quinolin-4-amine;2-Cyclohexyl-N-(3,4-dichlorophenyl)-1H-imidazo[4,5-c]quinolin-4-amine
Solubility:
10 mM in DMSO
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
LUF6000 has anti-inflammatory effect.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Milligrams-Grams
Boiling Point:
650.5±55.0 °C | Condition: Press: 760 Torr
Melting Point:
237-240 °C | Condition: Solv: methanol (67-56-1); water (7732-18-5)
Density:
1.401±0.06 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
UWJVRSIGHHSDSJ-UHFFFAOYSA-N
InChI:
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)
Canonical SMILES:
C1CCC(CC1)C2=NC3=C(N2)C(=NC4=CC=CC=C43)NC5=CC(=C(C=C5)Cl)Cl
1.A₃ adenosine receptor allosteric modulator induces an anti-inflammatory effect: in vivo studies and molecular mechanism of action.
Cohen S1, Barer F1, Bar-Yehuda S1, IJzerman AP2, Jacobson KA3, Fishman P1. Mediators Inflamm. 2014;2014:708746. doi: 10.1155/2014/708746. Epub 2014 Oct 13.
The A3 adenosine receptor (A3AR) is overexpressed in inflammatory cells and in the peripheral blood mononuclear cells of individuals with inflammatory conditions. Agonists to the A3AR are known to induce specific anti-inflammatory effects upon chronic treatment. LUF6000 is an allosteric compound known to modulate the A3AR and render the endogenous ligand adenosine to bind to the receptor with higher affinity. The advantage of allosteric modulators is their capability to target specifically areas where adenosine levels are increased such as inflammatory and tumor sites, whereas normal body cells and tissues are refractory to the allosteric modulators due to low adenosine levels. 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. The molecular mechanism of action points to deregulation of signaling proteins including PI3K, IKK, IκB, Jak-2, and STAT-1, resulting in decreased levels of NF-κB, known to mediate inflammatory effects.
2.A series of 2,4-disubstituted quinolines as a new class of allosteric enhancers of the adenosine A3 receptor.
Heitman LH1, Göblyös A, Zweemer AM, Bakker R, Mulder-Krieger T, van Veldhoven JP, de Vries H, Brussee J, Ijzerman AP. J Med Chem. 2009 Feb 26;52(4):926-31. doi: 10.1021/jm8014052.
The adenosine receptor subfamily consists of the adenosine A(1), A(2A), A(2B), and A(3) receptors, which are localized in a variety of tissues throughout the human body. It is, therefore, a challenge to develop receptor specific ligands with improved tissue selectivity. Allosteric modulators could have these therapeutic advantages over orthosteric ligands. In the present study, a series of 2,4-disubstituted quinolines were synthesized on the basis of the structure of LUF6000 (34). Compound 27 (LUF6096) was able to allosterically enhance agonist binding to a similar extent as 34. In addition, this new compound showed low, if any, orthosteric affinity for any of the adenosine receptors. In a functional assay, compound 27 showed improved activity in comparison to 34, as it increased both the intrinsic efficacy and the potency of the reference agonist Cl-IB-MECA at the human adenosine A(3) receptor.
3.Structure-activity relationships of new 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric enhancers of the A3 adenosine receptor.
Göblyös A1, Gao ZG, Brussee J, Connestari R, Santiago SN, Ye K, Ijzerman AP, Jacobson KA. J Med Chem. 2006 Jun 1;49(11):3354-61.
1H-Imidazo[4,5-c]quinolin-4-amine derivatives have been synthesized as allosteric modulators of the human A3 adenosine receptor (AR). Structural modifications were made at the 4-amino and 2 positions. The compounds were tested in both binding and functional assays, and many were found to be allosteric enhancers of the action of A3AR agonists by several different criteria. First, a potentiation of the maximum efficacy of the agonist Cl-IB-MECA was observed for numerous derivatives. Also, a number of these compounds decreased the rate of dissociation of the agonist [125I]I-AB-MECA from the A3AR. 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. The structural requirements for allosteric enhancement at the A3AR were distinct from the requirements to inhibit equilibrium binding. Thus, we have prepared allosteric enhancers of the human A3AR that have an improved allosteric effect in comparison to the inhibition of equilibrium binding at the orthosteric site.
4.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.
Deganutti G1, Cuzzolin A1, Ciancetta A1, Moro S2. Bioorg Med Chem. 2015 Jul 15;23(14):4065-71. doi: 10.1016/j.bmc.2015.03.039. Epub 2015 Mar 20.
The search for G protein-coupled receptors (GPCRs) allosteric modulators represents an active research field in medicinal chemistry. Allosteric modulators usually exert their activity only in the presence of the orthosteric ligand by binding to protein sites topographically different from the orthosteric cleft. They therefore offer potentially therapeutic advantages by selectively influencing tissue responses only when the endogenous agonist is present. The prediction of putative allosteric site location, however, is a challenging task. In facts, they are usually located in regions showing more structural variation among the family members. In the present work, we applied the recently developed Supervised Molecular Dynamics (SuMD) methodology to interpret at the molecular level the positive allosteric modulation mediated by LUF6000 toward the human adenosine A3 receptor (hA3 AR). Our data suggest at least two possible mechanisms to explain the experimental data available.
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CAS 890087-21-5 LUF 6000

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