4-hydroxy-[N,N',N,N,N,N-hexapropylhexa(aminoethyl)butanamide] | 1374033-11-0

• 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: 4-hydroxy-[N,N',N,N,N,N-hexapropylhexa(aminoethyl)butanamide]
• 英文别名: N-[2-[2-[2-[2-[2-(dipropylamino)ethyl-propylamino]ethyl-propylamino]ethyl-propylamino]ethyl-propylamino]ethyl]-4-hydroxybutanamide
• CAS: 1374033-11-0
• 化学式: C₃₂H₇₀N₆O₂
• 分子量: 570.947
• InChiKey: JYLHSVXIXSVBMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  40
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  65.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-hydroxy-[N,N',N,N,N,N-hexapropylhexa(aminoethyl)butanamide] 、 丙二酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到bis[N,N',N,N,N,N-hexapropylhexa(aminoethyl)amino]carbonyl propanoxymalonate
  参考文献：
  名称：

  Synthesis of decacationic [60]fullerene decaiodides giving photoinduced production of superoxide radicals and effective PDT-mediation on antimicrobial photoinactivation

  摘要：

  We report a novel class of highly water-soluble decacationic methano[60]fullerene decaiodides C-60[>M(C3N6+C3)(2)]-(I-)(10) [1-(I-)(10)] capable of co-producing singlet oxygen (Type-II) and highly reactive hydroxyl radicals, formed from superoxide radicals in Type-I photosensitizing reactions, upon illumination at both UVA and white light wavelengths. The O-2(-)center dot-production efficiency of 1-(I-)(10) was confirmed by using an O-2(-)center dot-reactive bis(2,4-dinitrobenzenesulfonyl)tetrafluorofluorescein probe and correlated to the photoinduced electron-transfer event going from iodide anions to C-3(60)*[>M(C3N6+C3)(2)] leading to C-60(-)center dot[>M(C3N6+C3)(2)]. Incorporation of a defined number (ten) of quaternary ammonium cationic charges per C60 in 1 was aimed to enhance its ability to target pathogenic Gram-positive and Gram-negative bacterial cells. We used the well-characterized malonato[60]fullerene diester monoadduct C-60[>M(t-Bu)(2)] as the starting fullerene derivative to provide a better synthetic route to C-60[>M(C3N6+C3)(2)] via transesterification reaction under trifluoroacetic acid catalyzed conditions. These compounds may be used as effective photosensitizers and nano-PDT drugs for photoinactivation of pathogens. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.052
• 作为产物：
  描述：

  γ-丁内酯 、 N,N',N,N,N,N-hexapropylhexa(aminoethyl)amine 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到4-hydroxy-[N,N',N,N,N,N-hexapropylhexa(aminoethyl)butanamide]
  参考文献：
  名称：

  Synthesis and Photodynamic Effect of New Highly Photostable Decacationically Armed [60]- and [70]Fullerene Decaiodide Monoadducts To Target Pathogenic Bacteria and Cancer Cells

  摘要：

  Novel water-soluble decacationically armed C-60 and C-70 decaiodide monoadducts, C-60- and C-70[>M(C3N6+C3)(2)], were synthesized, characterized, and applied as photosensitizers and potential nano-PDT agents against pathogenic bacteria and cancer cells. A high number of cationic charges per fullerene cage and H-bonding moieties were designed for rapid binding to the anionic residues displayed on the outer parts of bacterial cell walls. In the presence of a high number of electron-donating iodide anions as parts of quaternary ammonium salts in the arm region, we found that C-70[>M(C3N6+C3)(2)] produced more HO center dot than C-60[>M(C3N6+C3)(2)], in addition to O-1(2). This finding offers an explanation of the preferential killing of Gram-positive and Gram-negative bacteria by C-60[>M(C3N6+C3)(2)] and C-70[>M(C3N6+C3)(2)], respectively. The hypothesis is that O-1(2) can diffuse more easily into porous cell walls of Gram-positive bacteria to reach sensitive sites, while the less permeable Gram-negative bacterial cell wall needs the more reactive HO center dot to cause real damage.

  DOI：

  10.1021/jm3000664

文献信息

• Synthesis and Photodynamic Effect of New Highly Photostable Decacationically Armed [60]- and [70]Fullerene Decaiodide Monoadducts To Target Pathogenic Bacteria and Cancer Cells
  作者：Min Wang、Liyi Huang、Sulbha K Sharma、Seaho Jeon、Sammaiah Thota、Felipe F. Sperandio、Suhasini Nayka、Julie Chang、Michael R. Hamblin、Long Y. Chiang

  DOI：10.1021/jm3000664

  日期：2012.5.10

  Novel water-soluble decacationically armed C-60 and C-70 decaiodide monoadducts, C-60- and C-70[>M(C3N6+C3)(2)], were synthesized, characterized, and applied as photosensitizers and potential nano-PDT agents against pathogenic bacteria and cancer cells. A high number of cationic charges per fullerene cage and H-bonding moieties were designed for rapid binding to the anionic residues displayed on the outer parts of bacterial cell walls. In the presence of a high number of electron-donating iodide anions as parts of quaternary ammonium salts in the arm region, we found that C-70[>M(C3N6+C3)(2)] produced more HO center dot than C-60[>M(C3N6+C3)(2)], in addition to O-1(2). This finding offers an explanation of the preferential killing of Gram-positive and Gram-negative bacteria by C-60[>M(C3N6+C3)(2)] and C-70[>M(C3N6+C3)(2)], respectively. The hypothesis is that O-1(2) can diffuse more easily into porous cell walls of Gram-positive bacteria to reach sensitive sites, while the less permeable Gram-negative bacterial cell wall needs the more reactive HO center dot to cause real damage.
• Synthesis of decacationic [60]fullerene decaiodides giving photoinduced production of superoxide radicals and effective PDT-mediation on antimicrobial photoinactivation
  作者：Min Wang、Satyanarayana Maragani、Liyi Huang、Seaho Jeon、Taizoon Canteenwala、Michael R. Hamblin、Long Y. Chiang

  DOI：10.1016/j.ejmech.2013.01.052

  日期：2013.5

  We report a novel class of highly water-soluble decacationic methano[60]fullerene decaiodides C-60[>M(C3N6+C3)(2)]-(I-)(10) [1-(I-)(10)] capable of co-producing singlet oxygen (Type-II) and highly reactive hydroxyl radicals, formed from superoxide radicals in Type-I photosensitizing reactions, upon illumination at both UVA and white light wavelengths. The O-2(-)center dot-production efficiency of 1-(I-)(10) was confirmed by using an O-2(-)center dot-reactive bis(2,4-dinitrobenzenesulfonyl)tetrafluorofluorescein probe and correlated to the photoinduced electron-transfer event going from iodide anions to C-3(60)*[>M(C3N6+C3)(2)] leading to C-60(-)center dot[>M(C3N6+C3)(2)]. Incorporation of a defined number (ten) of quaternary ammonium cationic charges per C60 in 1 was aimed to enhance its ability to target pathogenic Gram-positive and Gram-negative bacterial cells. We used the well-characterized malonato[60]fullerene diester monoadduct C-60[>M(t-Bu)(2)] as the starting fullerene derivative to provide a better synthetic route to C-60[>M(C3N6+C3)(2)] via transesterification reaction under trifluoroacetic acid catalyzed conditions. These compounds may be used as effective photosensitizers and nano-PDT drugs for photoinactivation of pathogens. (C) 2013 Elsevier Masson SAS. All rights reserved.