Tebuconazole is an agricultural azole fungicide. It can also inhibit CYP51 (IC50s: 0.9 and 1.3 μM for Candida albicans CYP51 and truncated Homo sapiens CYP51, respectively).
Images & Validation
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Key Properties
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CAS Number
107534-96-3
MW
307.82
Purity
>98% (HPLC)
Formula
C16H22ClN3O
SMILES
CC(C)(C)C(CCc(cc1)ccc1Cl)(Cn1ncnc1)O
Target
P450
Solubility
DMSO:50 mg/mL (162.43 mM)
Bioactivity
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In Vivo
Animal model: Male Wistar rats. Dosage: 10, 25, and 50 mg/kg. Administration: p.o. once daily for 28 days. Result: Induced CYP1A1/2, CYP2B1/2, CYP2E1, and CYP3A proteins in liver. Decreased glutathione content and increased glutathione S-transferase, superoxide dismutase, catalase, and glutathione peroxidase activities in liver. Increased superoxide dismutase activities in kidney and testis. Decreased glutathione S-transferase activity in testis. Decreased serum testosterone concentration and cauda epididymal sperm count. Animal model: Male and female Sprague-Dawley rats. Dosage: 25, 50, and 100 mg/kg. Administration: Oral gavage (p.o.), for 10 days. Result: Increased fetal serum testosterone and progesterone levels. Increased the number of fetal Leydig cells per testis without inducing cell aggregation. Up-regulated the expression levels of Star, Cyp11a1, Hsd17b3, and Fshr. Increased phosphorylation of AKT1, ERK1/2, and mTOR, the level of BCL2, as well as the decrease of Beclin1, LC3B, and BAX.
In Vitro
Western blot analysis. Cell line: HepG2 cells. Concentration: 20, 40, 80 μM. Incubation time: 1-12 hours. Result: Increased the nuclear translocation of peroxisome proliferator-activated receptors and the expression of cluster of differentiation 36, fatty acid transport protein (FATP) 2, FATP5, and carnitine palmitoyltransferase 1. Apoptosis Analysis Cell line: Bovine mammary gland epithelial cells (MAC-T cells. Concentration: 100, 150, 200, 250, 500, 750 μM. Incubation time: 24 hours. Result: Decreased cells viability and proliferation and activates apoptotic cell death via the upregulation of pro-apoptotic proteins, such as cleaved caspases 3 and 8 and BAX. Induced loss of mitochondrial membrane potential in MAC-T cells. Induced mitochondria-mediated apoptotic MAC-T cell death by activating ER stress. Induced endoplasmic reticulum (ER) stress via the upregulation of Bip/GRP78; PDI; ATF4; CHOP; and ERO1-Lα.
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