LUF6000

LUF6000

Identifiers
IUPAC name 2-cyclohexyl-N-(3,4-dichlorophenyl)-3H-imidazo[4,5-c]quinolin-4-amine
CAS Number	890087-21-5
PubChem CID	11711282
IUPHAR/BPS	9446
ChemSpider	9886004
ChEMBL	ChEMBL475346
CompTox Dashboard (EPA)	DTXSID30470994
Chemical and physical data
Formula	C22H20Cl2N4
Molar mass	411.33 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CCC(CC1)C2=NC3=C(N2)C(=NC4=CC=CC=C43)NC5=CC(=C(C=C5)Cl)Cl
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) Key:UWJVRSIGHHSDSJ-UHFFFAOYSA-N

LUF6000 is an experimental drug which acts as a positive allosteric modulator of the adenosine A3 receptor. It has no effect on A3-mediated signalling by itself, but significantly enhances the effect of A3-selective agonists or partial agonists, and can even cause some adenosine A3 antagonists to produce agonist-like signalling. It has antiinflammatory effects in animal studies. ^{[1] [2] [3] [4] [5] [6]}

References

1. Göblyös A, Gao ZG, Brussee J, Connestari R, Santiago SN, Ye K, et al. (June 2006). "Structure-activity relationships of new 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric enhancers of the A3 adenosine receptor". Journal of Medicinal Chemistry. 49 (11): 3354–3361. doi:10.1021/jm060086s. PMC   2547348 . PMID   16722654.
2. Gao ZG, Ye K, Göblyös A, Ijzerman AP, Jacobson KA (December 2008). "Flexible modulation of agonist efficacy at the human A3 adenosine receptor by the imidazoquinoline allosteric enhancer LUF6000". BMC Pharmacology. 8: 20. doi: 10.1186/1471-2210-8-20 . PMC   2625337 . PMID   19077268.
3. Heitman LH, Göblyös A, Zweemer AM, Bakker R, Mulder-Krieger T, van Veldhoven JP, et al. (February 2009). "A series of 2,4-disubstituted quinolines as a new class of allosteric enhancers of the adenosine A3 receptor". Journal of Medicinal Chemistry. 52 (4): 926–931. doi:10.1021/jm8014052. PMID   19161279.
4. Gao ZG, Verzijl D, Zweemer A, Ye K, Göblyös A, Ijzerman AP, et al. (September 2011). "Functionally biased modulation of A(3) adenosine receptor agonist efficacy and potency by imidazoquinolinamine allosteric enhancers". Biochemical Pharmacology. 82 (6): 658–668. doi:10.1016/j.bcp.2011.06.017. PMC   3152598 . PMID   21718691.
5. Cohen S, Barer F, Bar-Yehuda S, IJzerman AP, Jacobson KA, Fishman P (2014). "A₃ adenosine receptor allosteric modulator induces an anti-inflammatory effect: in vivo studies and molecular mechanism of action". Mediators of Inflammation. 2014: 708746. doi: 10.1155/2014/708746 . PMC   4211160 . PMID   25374446.
6. Gao ZG, Chen W, Gao RR, Li J, Tosh DK, Hanover JA, et al. (October 2024). "Genetic and functional modulation by agonist MRS5698 and allosteric enhancer LUF6000 at the native A₃ adenosine receptor in HL-60 cells". Purinergic Signalling. 20 (5): 559–570. doi:10.1007/s11302-024-09992-z. PMC   11377395 . PMID   38416332.