H-His-Ala-Arg-Trp-Gly-Lys-Phe-Val-NH2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: H-His-Ala-Arg-Trp-Gly-Lys-Phe-Val-NH2
• 英文别名: (2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]propanoyl]amino]-5-guanidino-pentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]acetyl]amino]-N-[(1S)-1-benzyl-2-[[(1S)-1-carbamoyl-2-methyl-propyl]amino]-2-oxo-ethyl]hexanamide；(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]acetyl]amino]-N-[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]hexanamide
• 化学式: C₄₈H₇₀N₁₆O₈
• 分子量: 999.186
• InChiKey: UTGXIFLHQVQKOL-VXRRIGRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  72
• 可旋转键数：
  30
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  408
• 氢给体数：
  14
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  Fmoc-L-丙氨酸 、 Fmoc-L-苯丙氨酸 、 Fmoc-L-色氨酸(Boc)-OH 、 Fmoc-Pbf-L-精氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 生成 H-His-Ala-Arg-Trp-Gly-Lys-Phe-Val-NH2
  参考文献：
  名称：

  Design and Synthesis of Melanocortin Peptides with Candidacidal and Anti-TNF-α Properties

  摘要：

  alpha-Melanocyte stimulating hormone (alpha-MSH) is an endogenous antiinflammatory peptide with antimicrobial properties. We recently found that a synthetic analogue, [DNal(2')-7, Phe-12]-alpha-MSH (6-13), was considerably more potent in killing Candida albicans, but the anti-cytokine potential of the molecule was not investigated. Because molecules that combine candidacidal and antiinflammatory properties could be very useful in clinical practice, we measured the anti-TNF-alpha potential of [DNal(2')-7, Phe-12]-alpha-MSH (6-13) and explored effects of amino acid deletions and substitutions on both anti-Candida and anti-TNF-a activities. The results show that anti-TNF-a properties of this candidacidal peptide are only marginally increased relative to the native sequence. Conversely, we found that a closely related candidacidal analogue, [DNal(2')-7, Pro-12]-alpha-MSH (6-13), had enhanced anti-TNF-a effects in vitro and in vivo. This peptide, and other melanocortins with a similar dual effect, could be very useful to eradicate infections and, concurrently, reduce inflammatory reactions.

  DOI：

  10.1021/jm040890j

文献信息

• Design and Synthesis of Melanocortin Peptides with Candidacidal and Anti-TNF-α Properties
  作者：Paolo Grieco、Claudia Rossi、Stefano Gatti、Gualtiero Colombo、Andrea Carlin、Ettore Novellino、Teresa Lama、James M. Lipton、Anna Catania

  DOI：10.1021/jm040890j

  日期：2005.3.1

  alpha-Melanocyte stimulating hormone (alpha-MSH) is an endogenous antiinflammatory peptide with antimicrobial properties. We recently found that a synthetic analogue, [DNal(2')-7, Phe-12]-alpha-MSH (6-13), was considerably more potent in killing Candida albicans, but the anti-cytokine potential of the molecule was not investigated. Because molecules that combine candidacidal and antiinflammatory properties could be very useful in clinical practice, we measured the anti-TNF-alpha potential of [DNal(2')-7, Phe-12]-alpha-MSH (6-13) and explored effects of amino acid deletions and substitutions on both anti-Candida and anti-TNF-a activities. The results show that anti-TNF-a properties of this candidacidal peptide are only marginally increased relative to the native sequence. Conversely, we found that a closely related candidacidal analogue, [DNal(2')-7, Pro-12]-alpha-MSH (6-13), had enhanced anti-TNF-a effects in vitro and in vivo. This peptide, and other melanocortins with a similar dual effect, could be very useful to eradicate infections and, concurrently, reduce inflammatory reactions.