bis[N,N',N,N,N,N-hexapropylhexa(aminoethyl)amino]carbonyl propanoxymalonate | 1443440-82-1

• 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: bis[N,N',N,N,N,N-hexapropylhexa(aminoethyl)amino]carbonyl propanoxymalonate
• 英文别名: Bis[4-[2-[2-[2-[2-[2-(dipropylamino)ethyl-propylamino]ethyl-propylamino]ethyl-propylamino]ethyl-propylamino]ethylamino]-4-oxobutyl] propanedioate；bis[4-[2-[2-[2-[2-[2-(dipropylamino)ethyl-propylamino]ethyl-propylamino]ethyl-propylamino]ethyl-propylamino]ethylamino]-4-oxobutyl] propanedioate
• CAS: 1443440-82-1
• 化学式: C₆₇H₁₄₀N₁₂O₆
• 分子量: 1209.93
• InChiKey: RIKFQYXTMCQVRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  85
• 可旋转键数：
  66
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  bis[N,N',N,N,N,N-hexapropylhexa(aminoethyl)amino]carbonyl propanoxymalonate 、 碘甲烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以92%的产率得到bis[N,N',N,N,N,N-hexapropylhexa(aminoethyl)amino]carbonylpropanoxymalonate deca(quaternary methylammonium iodide)
  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：

  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

文献信息

• 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.