Synonym
KMUP-3; KMUP 3; KMUP3;
IUPAC/Chemical Name
1,3-dimethyl-7-(2-(4-(4-nitrophenyl)piperazin-1-yl)ethyl)-3,7-dihydro-1H-purine-2,6-dione
InChi Key
WUNWRZDRKZFAHV-UHFFFAOYSA-N
InChi Code
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
SMILES Code
CN1C(N(C)C(N=CN2CCN3CCN(C4=CC=C([N+]([O-])=O)C=C4)CC3)=C2C1=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
413.43
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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.
