Cas No.: | 36945-98-9 |
Chemical Name: | ICILLIN |
Synonyms: | 2(1H)-Pyrimidinone,3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-;3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one;Icilin;AG 3-5;AG-3-5;1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyrimidin-2-one;3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one;Icilin(AG 3-5);2(1H)-Pyrimidinone, 3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-;ICILLIN;CS70PZQ4QJ;C16H13N3O4;3,6-Dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-2(1H)-pyrimidinone;3,4-Dihydro-3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-(1H)-pyrimidin-2-one;1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyrimidine-2-one;SMR000299977 |
SMILES: | O=C1N([H])C(C2C([H])=C([H])C([H])=C(C=2[H])[N+](=O)[O-])=C([H])C([H])([H])N1C1=C([H])C([H])=C([H])C([H])=C1O[H] |
Formula: | C16H13N3O4 |
M.Wt: | 311.2921 |
Purity: | >98% |
Sotrage: | 2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO |
Description: | Icilin(AG 3-5) is a synthetic super-agonist of TRPM8 ion channel.IC50 value:Target: TRPM8in vitro: icilin, a super-cooling agent, down-regulated the expression of cell cycle signature genes and caused G1 arrest in PC-3 prostate cancer cells. icilin affected cell cycle-related transcriptional modules and identified E2F1 transcription factor as a target master regulator of icilin. icilin reduced the activity and expression levels of E2F1 [1]. Icilin concentration-response curves were significantly shifted to the right when pH was lowered from 7.3 to 6.9, whereas those with menthol were unaltered in solutions of pH 6.1 [2]. Icilin modulated the expression level of various cell cycle regulators at transcription or post-translational levels. In addition, icilin activated JNK and p38 kinase pathways, but not ERK [4].in vivo: Rats injected with icilin (0.5, 1, 2.5, 5mg/kg, i.p.) displayed dose-related WDS that were inhibited by pretreatment with a fixed dose of clonidine (0.15 mg/kg, s.c.). Shaking behavior caused by a fixed dose (2.5mg/kg) of icilin was also inhibited in a dose-related manner by clonidine pretreatment (0.03-0.15 mg/kg, s.c.) and reduced by clonidine posttreatment (0.15 mg/kg, s.c.) [3]. |
References: | [1]. Lee S, et al. Icilin inhibits E2F1-mediated cell cycle regulatory programs in prostate cancer. Biochem Biophys Res Commun. 2013 Nov 29;441(4):1005-10. [2]. Andersson DA, et al. TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH. J Neurosci. 2004 Jun 9;24(23):5364-9. [3]. Kim J, et al. Icilin-evoked behavioral stimulation is attenuated by alpha-adrenoceptor activation. Brain Res. 2011 Apr 12;1384:110-7. [4]. Kim SH, et al. Icilin induces G1 arrest through activating JNK and p38 kinase in a TRPM8-independent manner. Biochem Biophys Res Commun. 2011 Mar 4;406(1):30-5. |