D,L-2-aminohexadecanoic acid hydrochloride | 5440-52-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: D,L-2-aminohexadecanoic acid hydrochloride
• 英文别名: 2-amino-D,L-hexadecanoic acid hydrochloride；2-Aminohexadecanoic acid--hydrogen chloride (1/1)；2-aminohexadecanoic acid;hydrochloride
• CAS: 5440-52-8
• 化学式: C₁₆H₃₃NO₂*ClH
• 分子量: 307.904
• InChiKey: FLTOZILZLWBKNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-乙酰基-5,5-二甲基-1,3-环己二酮 、 D,L-2-aminohexadecanoic acid hydrochloride 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以55%的产率得到2-((1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl)amino)hexadecanoic acid
  参考文献：
  名称：

  Active immunisation of mice with GnRH lipopeptide vaccine candidates: Importance of T helper or multi-dimer GnRH epitope

  摘要：

  Active immunisation against gonadotropin releasing hormone (GnRH) is a potential alternative to surgical castration. This study focused on the development of a GnRH subunit lipopeptide vaccine. A library of vaccine candidates that contained one or more (up to eight) copies of monomeric or dimeric GnRH peptide antigen, an adjuvanting lipidic moiety based on lipoamino acids, and an additional T helper epitope, was synthesised by solid phase peptide synthesis. The candidates were evaluated in vivo in order to determine the minimal components of this vaccine necessary to induce a systemic immune response. BALB/c mice were immunised with GnRH lipopeptide conjugates, co-administered with or without Complete Freund's Adjuvant, followed by two additional immunisations. Significant GnRH-specific IgG titres were detected in sera obtained from mice immunised with four of the seven lipopeptides tested, with an increase in titres observed after successive immunisations. This study highlights the importance of for epitope optimisation and delivery system design when producing anti-hapten antibodies in vivo. The results of this study also contribute to the development of future clinical and veterinary immunocontraceptives.

  DOI：

  10.1016/j.bmc.2014.06.052
• 作为产物：
  描述：

  2-十四烷基-2-乙酰氨基丙二酸二乙酯 在 盐酸 作用下， 生成 D,L-2-aminohexadecanoic acid hydrochloride
  参考文献：
  名称：

  Pro-apoptotic activity of lipidic α-amino acids isolated from Protopalythoa variabilis

  摘要：

  Lipidic alpha-amino acids (LAAs) have been described as non-natural amino acids with long saturated or unsaturated aliphatic chains. In the continuing prospect to discover anticancer agents from marine sources, we have obtained a mixture of two cytotoxic LAAs (1a and 1b) from the zoanthid Protopalythoa variabilis. The anti-proliferative potential of 14 synthetic LAAs and 1a/1b were evaluated on four tumor cell lines (HCT-8, SF-295, MDA-MB-435, and HL-60). Five of the synthetic LAAs showed high percentage of tumor cell inhibition, while 1a/1b completely inhibited tumor cell growth. Additionally, apoptotic effects of 1a/1b were studied on HL-60 cell line. 1a/1b-treated cells showed apoptosis morphology, loss of mitochondrial potential, and DNA fragmentation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.027

文献信息

• Hair or skin conditioning composition comprising hydrophobically modified cationic thickening polymer
  申请人：The Procter & Gamble Company

  公开号：US20040247550A1

  公开（公告）日：2004-12-09

  Disclosed is a hair or skin conditioning composition comprising by weight: (a) from about 0.01% to about 5% of a hydrophobically modified cationic thickening polymer; (b) from about 0.05% to about 10% of a surfactant selected from the group consisting of cationic surfactant, nonionic surfactant, and mixtures thereof; and (c) from about 0.1% to about 10% of a hydrophobically modified silicone; and (d) an aqueous carrier. The conditioning composition of the present invention has a suitable rheology for conditioning compositions, and provides conditioning benefits. The composition is especially suitable for hair care products such as hair conditioning products for rinse-off use.

  本发明公开了一种头发或皮肤调理组合物，按重量计包括：（a）约 0.01%至约 5%的疏水改性阳离子增稠聚合物；（b）约 0.05%至约 10%的选自阳离子表面活性剂、非离子表面活性剂及其混合物组的表面活性剂；以及（c）约 0.1%至约 10%的疏水改性硅氧烷；以及（d）水性载体。本发明的调理组合物具有适合调理组合物的流变性，并提供调理功效。该组合物尤其适用于护发产品，如冲洗型护发产品。
• α-1,4-Galactosyltransferase-catalyzed glycosylation of sugar and lipid modified Leu-enkephalins
  作者：Pavla Simerska、Michelle P. Christie、Daryn Goodwin、Freda E.-C. Jen、Michael P. Jennings、Istvan Toth

  DOI：10.1016/j.molcatb.2013.08.018

  日期：2013.12

  Glycosylation of therapeutic peptides has been reported to improve delivery and targeting of various vaccines and drugs to specific cells/tissues. However, chemical synthesis of complex oligosaccharide derivatives via conventional methods can be challenging due to the need for several orthogonal hydroxyl group protections. Liposaccharyl galactosyltransferase C, a naturally occurring glycosyltransferase enzyme from Neisseria meningitidis, was found to have the ability to transfer a galactosyl moiety to glyco(lipo)peptides. An enzymatic glycosylation of Leu-enkephalin glyco(lipo)peptides was developed and optimized in this study in order to prepare pain regulating peptides with potentially improved central nervous system delivery. (C) 2013 Elsevier B.V. All rights reserved.
• Pro-apoptotic activity of lipidic α-amino acids isolated from Protopalythoa variabilis
  作者：Diego Veras Wilke、Paula Christine Jimenez、Renata Mendonça Araújo、Wildson Max Barbosa da Silva、Otília Deusdênia Loiola Pessoa、Edilberto Rocha Silveira、Claudia Pessoa、Manoel Odorico de Moraes、Mariusz Skwarczynski、Pavla Simerska、Istvan Toth、Letícia Veras Costa-Lotufo

  DOI：10.1016/j.bmc.2010.09.027

  日期：2010.11

  Lipidic alpha-amino acids (LAAs) have been described as non-natural amino acids with long saturated or unsaturated aliphatic chains. In the continuing prospect to discover anticancer agents from marine sources, we have obtained a mixture of two cytotoxic LAAs (1a and 1b) from the zoanthid Protopalythoa variabilis. The anti-proliferative potential of 14 synthetic LAAs and 1a/1b were evaluated on four tumor cell lines (HCT-8, SF-295, MDA-MB-435, and HL-60). Five of the synthetic LAAs showed high percentage of tumor cell inhibition, while 1a/1b completely inhibited tumor cell growth. Additionally, apoptotic effects of 1a/1b were studied on HL-60 cell line. 1a/1b-treated cells showed apoptosis morphology, loss of mitochondrial potential, and DNA fragmentation. (C) 2010 Elsevier Ltd. All rights reserved.
• Corrigendum to “Pro-apoptotic activity of lipidic α-amino acids isolated from Protopalythoa variabilis” [Bioorg. Med. Chem. 18 (2010) 7997–8004]
  作者：Diego Veras Wilke、Paula Christine Jimenez、Renata Mendonça Araújo、Wildson Max Barbosa da Silva、Otília Deusdênia Loiola Pessoa、Edilberto Rocha Silveira、Claudia Pessoa、Manoel Odorico de Moraes、Mariusz Skwarczynski、Pavla Simerska、Istvan Toth、Letícia Veras Costa-Lotufo

  DOI：10.1016/j.bmc.2010.12.041

  日期：2011.2
• Active immunisation of mice with GnRH lipopeptide vaccine candidates: Importance of T helper or multi-dimer GnRH epitope
  作者：Daryn Goodwin、Pavla Simerska、Cheng-Hung Chang、Friederike M. Mansfeld、Pegah Varamini、Michael J. D’Occhio、Istvan Toth

  DOI：10.1016/j.bmc.2014.06.052

  日期：2014.9

  Active immunisation against gonadotropin releasing hormone (GnRH) is a potential alternative to surgical castration. This study focused on the development of a GnRH subunit lipopeptide vaccine. A library of vaccine candidates that contained one or more (up to eight) copies of monomeric or dimeric GnRH peptide antigen, an adjuvanting lipidic moiety based on lipoamino acids, and an additional T helper epitope, was synthesised by solid phase peptide synthesis. The candidates were evaluated in vivo in order to determine the minimal components of this vaccine necessary to induce a systemic immune response. BALB/c mice were immunised with GnRH lipopeptide conjugates, co-administered with or without Complete Freund's Adjuvant, followed by two additional immunisations. Significant GnRH-specific IgG titres were detected in sera obtained from mice immunised with four of the seven lipopeptides tested, with an increase in titres observed after successive immunisations. This study highlights the importance of for epitope optimisation and delivery system design when producing anti-hapten antibodies in vivo. The results of this study also contribute to the development of future clinical and veterinary immunocontraceptives.