CU-CPT9a

CU-CPT9a
Identifiers
	IUPAC name 4-(7-methoxyquinolin-4-yl)-2-methylphenol;
CAS Number	2165340-32-7;
PubChem CID	135567383;
ChemSpider	65323639;
Chemical and physical data
Formula	C17H15NO2
Molar mass	265.312 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C=CC(=C1)C2=C3C=CC(=CC3=NC=C2)OC)O;
	InChI InChI=1S/C17H15NO2/c1-11-9-12(3-6-17(11)19)14-7-8-18-16-10-13(20-2)4-5-15(14)16/h3-10,19H,1-2H3; Key:HNYBTVKYLVLWCB-UHFFFAOYSA-N;

CU-CPT9a is a drug which acts as a potent and selective antagonist of Toll-like receptor 8 (TLR8), with an IC₅₀ of 0.5nM. Activation of toll-like receptors triggers release of cytokines and other signalling factors, leading to inflammation. This is an essential part of the immune system's response to infection, but chronic activation of TLR signalling is thought to be involved in various inflammatory and autoimmune disorders. CU-CPT9a has immunosuppressant properties, and may have applications in the treatment of autoimmune disorders, as well as being used in scientific research into the function of TLR8.^[1]^[2]^[3]^[4]^[5]

References

^ Zhang S, Hu Z, Tanji H, Jiang S, Das N, Li J, et al. (January 2018). "Small-molecule inhibition of TLR8 through stabilization of its resting state". Nature Chemical Biology. 14 (1): 58–64. doi:10.1038/nchembio.2518. PMC 5726935. PMID 29155428.
^ Hu Z, Tanji H, Jiang S, Zhang S, Koo K, Chan J, et al. (October 2018). "Small-Molecule TLR8 Antagonists via Structure-Based Rational Design". Cell Chemical Biology. 25 (10): 1286–1291.e3. doi:10.1016/j.chembiol.2018.07.004. PMC 6195466. PMID 30100350.
^ Yang J, Lan J, Du H, Zhang X, Li A, Zhang X, et al. (March 2019). "Icariside II induces cell cycle arrest and differentiation via TLR8/MyD88/p38 pathway in acute myeloid leukemia cells". European Journal of Pharmacology. 846: 12–22. doi:10.1016/j.ejphar.2018.12.026. PMID 30579933. S2CID 58567568.
^ Venegas FA, Köllisch G, Mark K, Diederich WE, Kaufmann A, Bauer S, et al. (September 2019). "The Bacterial Product Violacein Exerts an Immunostimulatory Effect Via TLR8". Scientific Reports. 9 (1): 13661. Bibcode:2019NatSR...913661V. doi:10.1038/s41598-019-50038-x. PMC 6754391. PMID 31541142.
^ Ehrnström B, Kojen JF, Giambelluca M, Ryan L, Moen SH, Hu Z, et al. (April 2020). "TLR8 and complement C5 induce cytokine release and thrombin activation in human whole blood challenged with Gram-positive bacteria". Journal of Leukocyte Biology. 107 (4): 673–683. doi:10.1002/JLB.3A0120-114R. hdl:11250/2644510. PMID 32083344.

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[1] Zhang S, Hu Z, Tanji H, Jiang S, Das N, Li J, et al. (January 2018). "Small-molecule inhibition of TLR8 through stabilization of its resting state". Nature Chemical Biology. 14 (1): 58–64. doi:10.1038/nchembio.2518. PMC 5726935. PMID 29155428.

[2] Hu Z, Tanji H, Jiang S, Zhang S, Koo K, Chan J, et al. (October 2018). "Small-Molecule TLR8 Antagonists via Structure-Based Rational Design". Cell Chemical Biology. 25 (10): 1286–1291.e3. doi:10.1016/j.chembiol.2018.07.004. PMC 6195466. PMID 30100350.

[3] Yang J, Lan J, Du H, Zhang X, Li A, Zhang X, et al. (March 2019). "Icariside II induces cell cycle arrest and differentiation via TLR8/MyD88/p38 pathway in acute myeloid leukemia cells". European Journal of Pharmacology. 846: 12–22. doi:10.1016/j.ejphar.2018.12.026. PMID 30579933. S2CID 58567568.

[4] Venegas FA, Köllisch G, Mark K, Diederich WE, Kaufmann A, Bauer S, et al. (September 2019). "The Bacterial Product Violacein Exerts an Immunostimulatory Effect Via TLR8". Scientific Reports. 9 (1): 13661. Bibcode:2019NatSR...913661V. doi:10.1038/s41598-019-50038-x. PMC 6754391. PMID 31541142.

[5] Ehrnström B, Kojen JF, Giambelluca M, Ryan L, Moen SH, Hu Z, et al. (April 2020). "TLR8 and complement C5 induce cytokine release and thrombin activation in human whole blood challenged with Gram-positive bacteria". Journal of Leukocyte Biology. 107 (4): 673–683. doi:10.1002/JLB.3A0120-114R. hdl:11250/2644510. PMID 32083344.

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Identifiers

IUPAC name 4-(7-methoxyquinolin-4-yl)-2-methylphenol
CAS Number	2165340-32-7
PubChem CID	135567383
ChemSpider	65323639
Chemical and physical data
Formula	C₁₇H₁₅NO₂
Molar mass	265.312 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=C(C=CC(=C1)C2=C3C=CC(=CC3=NC=C2)OC)O
InChI InChI=1S/C17H15NO2/c1-11-9-12(3-6-17(11)19)14-7-8-18-16-10-13(20-2)4-5-15(14)16/h3-10,19H,1-2H3 Key:HNYBTVKYLVLWCB-UHFFFAOYSA-N

CU-CPT9a

See also

References