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

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

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[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.

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