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N-dodecanoyl-L-Homoserine lactone Sale

(Synonyms: 十二烷酰-L-高丝氨酸内酯,C12-HSL) 目录号 : GC44355

C12 quorum-sensing lactone

N-dodecanoyl-L-Homoserine lactone Chemical Structure

Cas No.:137173-46-7

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5mg
¥546.00
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10mg
¥1,036.00
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25mg
¥2,394.00
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50mg
¥3,990.00
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Sample solution is provided at 25 µL, 10mM.

Description

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-dodecanoyl-L-Homoserine lactone (C12-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria. [1][2][3] In addition to regulating bacterial functions, C12-HSL activates NF-κB in RAW 264.7 macrophages, increasing the expression of TNF-α, interleukin-1β (IL-1β), and IL-8, while other lactones do not.[4] In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells. It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-Homoserine lactone which is produced at different times in biofilm development[6] and has different cellular effects.[5]

Reference:
[1]. Kuo, A., Blough, N.V., and Dunlap, P.V. Multiple N-acyl-L-homoserine lactone autoinducers of luminescence in the marine symbiotic bacterium Vibrio fischeri. Journal of Bacteriology 176(24), 7558-7565 (1994).
[2]. Lithgow, J.K., Wilkinson, A., Hardman, A., et al. The regulatory locus cinRI in Rhizobium leguminosarum controls a network of quorum-sensing loci. Molecular Microbiology 37(1), 81-97 (2000).
[3]. McClean, K.H., Winson, M.K., Fish, L., et al. Quorum-sensing and Chromobacterium violaceum: Exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiology 143, 3703-3711 (1997).
[4]. Gomi, K., Kikuchi, T., Tokue, Y., et al. Mouse and human cell activation by N-dodecanoyl-DL-homoserine lactone, a Chromobacterium violaceum autoinducer. Infection and Immunity 74(12), 7029-7031 (2006).
[5]. Kristiansen, S., Bjarnsholt, T., Adeltoft, D., et al. The Pseudomonas aeruginosa autoinducer dodecanoyl-homoserine lactone inhibits the putrescine synthesis in human cells. Acta Pathologica, Microbiologica, et Immunologica Scandinavica 116, 361-371 (2008).
[6]. Huang, Y.L., Ki, J.S., Lee, O.O., et al. Evidence for the dynamics of acyl homoserine lactone and AHL-producing bacteria during subtidal biofilm formation. ISME Journal 1-9 (2008).

化学性质

Cas No. 137173-46-7 SDF
别名 十二烷酰-L-高丝氨酸内酯,C12-HSL
化学名 N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide
Canonical SMILES CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
分子式 C16H29NO3 分子量 283.4
溶解度 30mg/ml in DMSO, or in DMF 储存条件 Store at -20°C
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
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1 mg 5 mg 10 mg
1 mM 3.5286 mL 17.6429 mL 35.2858 mL
5 mM 0.7057 mL 3.5286 mL 7.0572 mL
10 mM 0.3529 mL 1.7643 mL 3.5286 mL
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