FICZ

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Chemical Structure| 172922-91-7 同义名 : 6-Formylindolo[3,2-b]carbazole
CAS号 : 172922-91-7
货号 : A296079
分子式 : C19H12N2O
纯度 : 98%
分子量 : 284.31
MDL号 : MFCD09879259
存储条件：

Pure form Inert atmosphere, 2-8°C

In solvent -20°C:3-6个月-80°C:12个月
溶解度 :

DMSO: 9 mg/mL(31.66 mM)，配合低频超声，并水浴加热至45℃助溶，注意：DMSO长时间开封后，会吸水并导致溶解能力下降，请避免使用长期开封的DMSO
动物实验配方：
生物活性
描述 The aryl hydrocarbon receptor (AHR) is a transcription factor that regulates gene expressions in response to endogenous and exogenous signals. FICZ is a high potency AHR agonist with a Kd value of 0.07 nM[3]. The 24-h treatment with 100 nM FICZ significantly induced EROD activity in wild-type mouse hepatoma Hepa-1 cells. FICZ at the concentration of 1 nM increased the mRNA level of CYP1A1 in wild-type cells, but the induction was transient and declined 3h after the treatment. In c37 cells, FICA-induced CYP1A1 mRNA expression was sustained[4]. In human liver microsomes, a 20-min preincubation with a mixture of CYP1A1/1A2 and CYP1B1 antibodies almost completely blocked (93%) the NADPH-dependent FICZ metabolism. In HepG2 cells treated with 5 nM FICZ, the addition of 5 μM αNF attenuated the complete depletion of intracellular levels of FICZ as compared to non-αNF treated cells. CYP1A1 catalyzes the hydroxylation of FICZ with extremely high efficiency (Kcat/Km = 8.1 × 107M-1s-1[5]. In a mouse model of mite-induced chronic dermatitis, treatment with FICZ ointment at the dose of 10-3 mM for 2 weeks significantly improved the dermatitis compared to control mice[6].
实验方案
1mg 5mg 10mg

1 mM

5 mM

10 mM

3.52mL

0.70mL

0.35mL

17.59mL

3.52mL

1.76mL

35.17mL

7.03mL

3.52mL
参考文献

[1]Moura-Alves P, Fae K, et al. AhR sensing of bacterial pigments regulates antibacterial defence. Nature. 2014 Aug 28;512(7515):387-92.

[2]Wei YD, et al. Rapid and transient induction of CYP1A1 gene expression in human cells by the tryptophan photoproduct 6-formylindolo[3,2-b] carbazole. Chem Biol Interact. 1998 Mar 12;110(1-2):39-55.

[3]Rannug U, Rannug A, Sjöberg U, Li H, Westerholm R, Bergman J. Structure elucidation of two tryptophan-derived, high affinity Ah receptor ligands. Chem Biol. 1995 Dec;2(12):841-5. doi: 10.1016/1074-5521(95)90090-x. PMID: 8807817.

[4]Wei YD, Bergander L, Rannug U, Rannug A. Regulation of CYP1A1 transcription via the metabolism of the tryptophan-derived 6-formylindolo[3,2-b]carbazole. Arch Biochem Biophys. 2000 Nov 1;383(1):99-107. doi: 10.1006/abbi.2000.2037. PMID: 11097181.

[5]Wincent E, Amini N, Luecke S, Glatt H, Bergman J, Crescenzi C, Rannug A, Rannug U. The suggested physiologic aryl hydrocarbon receptor activator and cytochrome P4501 substrate 6-formylindolo[3,2-b]carbazole is present in humans. J Biol Chem. 2009 Jan 30;284(5):2690-2696. doi: 10.1074/jbc.M808321200. Epub 2008 Dec 2. PMID: 19054769.

[6]Kiyomatsu-Oda M, Uchi H, Morino-Koga S, Furue M. Protective role of 6-formylindolo[3,2-b]carbazole (FICZ), an endogenous ligand for arylhydrocarbon receptor, in chronic mite-induced dermatitis. J Dermatol Sci. 2018 Jun;90(3):284-294. doi: 10.1016/j.jdermsci.2018.02.014. Epub 2018 Feb 21. PMID: 29500077.