KMUP-3

• CAT Number: I030114
• CAS Number: 421556-16-3
• Molecular Formula: C19H23N7O4
• Molecular Weight: 413.43
• Purity: 98%
• Synonyms: KMUP-3; KMUP 3; KMUP3
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 1,3-dimethyl-7-(2-(4-(4-nitrophenyl)piperazin-1-yl)ethyl)-3,7-dihydro-1H-purine-2,6-dione
• InChI: InChI=1S/C19H23N7O4/c1-21-17-16(18(27)22(2)19(21)28)25(13-20-17)12-9-23-7-10-24(11-8-23)14-3-5-15(6-4-14)26(29)30/h3-6,13H,7-12H2,1-2H3
• InChIKey: WUNWRZDRKZFAHV-UHFFFAOYSA-N
• SMILES: CN1C(N(C)C(N=CN2CCN3CCN(C4=CC=C([N+]([O-])=O)C=C4)CC3)=C2C1=O)=O

KMUP-3 is an enhancer of cGMP activity. It also acts as an aortic smooth muscle relaxant.

Reference

1: Liu CP, Yeh JL, Liou SF, Wu BN, Chen IJ. Phosphodiesterase inhibitor KMUP-3 displays cardioprotection via protein kinase G and increases cardiac output via G-protein-coupled receptor agonist activity and Ca(2+) sensitization. Kaohsiung J Med Sci. 2016 Feb;32(2):55-67. doi: 10.1016/j.kjms.2016.01.005. Epub 2016 Feb 24. PubMed PMID: 26944323.
2: Winardi W, Wang CJ, Lin CL, Wu SC, Tsai HP, Kuo YH, Lee MY, Chen IJ, Kwan AL. Attenuation of cerebral vasospasm following experimental subarachnoid hemorrhage by the bronchodilator KMUP-3. Acta Neurochir Suppl. 2013;115:239-46. doi: 10.1007/978-3-7091-1192-5_43. PubMed PMID: 22890675.
3: Liu CP, Yeh JL, Wu BN, Chai CY, Chen IJ, Lai WT. KMUP-3 attenuates ventricular remodelling after myocardial infarction through eNOS enhancement and restoration of MMP-9/TIMP-1 balance. Br J Pharmacol. 2011 Jan;162(1):126-35. doi: 10.1111/j.1476-5381.2010.01024.x. PubMed PMID: 20840538; PubMed Central PMCID: PMC3012411.
4: Wu BN, Chen CW, Liou SF, Yeh JL, Chung HH, Chen IJ. Inhibition of proinflammatory tumor necrosis factor-{alpha}-induced inducible nitric-oxide synthase by xanthine-based 7-[2-[4-(2-chlorobenzene)piperazinyl]ethyl]-1,3-dimethylxanthine (KMUP-1) and 7-[2-[4-(4-nitrobenzene)piperazinyl]ethyl]-1, 3-dimethylxanthine (KMUP-3) in rat trachea: The involvement of soluble guanylate cyclase and protein kinase G. Mol Pharmacol. 2006 Sep;70(3):977-85. Epub 2006 Jun 5. PubMed PMID: 16754782.
5: Lin RJ, Wu BN, Lo YC, An LM, Dai ZK, Lin YT, Tang CS, Chen IJ. A xanthine-based epithelium-dependent airway relaxant KMUP-3 (7-[2-[4-(4-nitrobenzene)piperazinyl]ethyl]-1,3-dimethylxanthine) increases respiratory performance and protects against tumor necrosis factor-alpha-induced tracheal contraction, involving nitric oxide release and expression of cGMP and protein kinase G. J Pharmacol Exp Ther. 2006 Feb;316(2):709-17. Epub 2005 Oct 18. PubMed PMID: 16234412.
6: Wu BN, Chen IC, Lin RJ, Chiu CC, An LM, Chen IJ. Aortic smooth muscle relaxants KMUP-3 and KMUP-4, two nitrophenylpiperazine derivatives of xanthine, display cGMP-enhancing activity: roles of endothelium, phosphodiesterase, and K+ channel. J Cardiovasc Pharmacol. 2005 Nov;46(5):600-8. PubMed PMID: 16220066.