4-(4′-aminobutyl)-1,10-phenanthroline | 1033726-24-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 4-(4′-aminobutyl)-1,10-phenanthroline
• 英文别名: 4-(Aminobutyl)-1,10-phenanthroline；4-(1,10-phenanthrolin-4-yl)butan-1-amine
• CAS: 1033726-24-7
• 化学式: C₁₆H₁₇N₃
• 分子量: 251.331
• InChiKey: PQFCYOBLSQWAAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二[(1-氧代-2-丙烯基)氨基]-乙酸 、 4-(4′-aminobutyl)-1,10-phenanthroline 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 48.0h， 生成 2-[3-[[3-[[Carboxy-(prop-2-enoylamino)methyl]amino]-3-oxopropyl]-[4-(1,10-phenanthrolin-4-yl)butyl]amino]propanoylamino]-2-(prop-2-enoylamino)acetic acid
  参考文献：
  名称：

  Luminescent Rhenium and Ruthenium Complexes of an Amphoteric Poly(amidoamine) Functionalized with 1,10-Phenanthroline

  摘要：

  A new amphoteric copolymer, PhenISA, has been obtained by copolymerization of 4-(4'-aminobutyl)-1,10-phenanthroline (BAP) with 2-methylpiperazine and bis(acrylamido)acetic acid (BAC) (6% of phenanthroline-containing repeating units). The copolymer showed excellent solubility in water, where it self-aggregated to give clear nanoparticle suspensions (hydrodynamic diameter = 21 +/- 2 nm, by dynamic light scattering (DLS) analysis). The phenanthroline pendants of the polymer stably coordinated either Re(CO)(3)(+) or Ru(phen)(2)(2+) fragments, affording luminescent Re-PhenISA, Re-Py-PhenISA, and Ru-PhenISA polymer complexes, emitting from triplet metal-to-ligand charge transfer ((MLCT)-M-3) excited states (with lambda(em) = 608, 571, and 614 nm, respectively, and photoluminescence quantum yields Phi(em) = 0.7%, 4.8%, and 4.1%, in aerated water solution, respectively). DLS analyses indicated that the polymer complexes maintained the nanosize of PhenISA. All the complexes were stable under physiological conditions (pH 7.4, 0.15 M NaCl) in the presence of an excess of the ubiquitous competitor cysteine. In vitro viability assays showed no toxicity of Re-Py-PhenISA and Ru-PhenISA complexes, at concentrations in the range of 0.5-50 mu M (calculated on the metal-containing unit), toward HEK-293 (human embryonic kidney) cells. A preliminary investigation of internalization in HEK-293 cells, by means of fluorescence confocal microscopy, showed that Ru-PhenISA enters cells via an endocytic pathway and, subsequently, homogeneously diffuse within the cytoplasm across the vesicle membranes.

  DOI：

  10.1021/ic301616b
• 作为产物：
  描述：

  4-甲基-1,10-邻二氮杂菲 、 1-(3-溴丙基)-2,2,5,5-四甲基-1-氮杂-2,5-二硅杂环戊烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 348.0h， 以54%的产率得到4-(4′-aminobutyl)-1,10-phenanthroline
  参考文献：
  名称：

  Luminescent Rhenium and Ruthenium Complexes of an Amphoteric Poly(amidoamine) Functionalized with 1,10-Phenanthroline

  摘要：

  A new amphoteric copolymer, PhenISA, has been obtained by copolymerization of 4-(4'-aminobutyl)-1,10-phenanthroline (BAP) with 2-methylpiperazine and bis(acrylamido)acetic acid (BAC) (6% of phenanthroline-containing repeating units). The copolymer showed excellent solubility in water, where it self-aggregated to give clear nanoparticle suspensions (hydrodynamic diameter = 21 +/- 2 nm, by dynamic light scattering (DLS) analysis). The phenanthroline pendants of the polymer stably coordinated either Re(CO)(3)(+) or Ru(phen)(2)(2+) fragments, affording luminescent Re-PhenISA, Re-Py-PhenISA, and Ru-PhenISA polymer complexes, emitting from triplet metal-to-ligand charge transfer ((MLCT)-M-3) excited states (with lambda(em) = 608, 571, and 614 nm, respectively, and photoluminescence quantum yields Phi(em) = 0.7%, 4.8%, and 4.1%, in aerated water solution, respectively). DLS analyses indicated that the polymer complexes maintained the nanosize of PhenISA. All the complexes were stable under physiological conditions (pH 7.4, 0.15 M NaCl) in the presence of an excess of the ubiquitous competitor cysteine. In vitro viability assays showed no toxicity of Re-Py-PhenISA and Ru-PhenISA complexes, at concentrations in the range of 0.5-50 mu M (calculated on the metal-containing unit), toward HEK-293 (human embryonic kidney) cells. A preliminary investigation of internalization in HEK-293 cells, by means of fluorescence confocal microscopy, showed that Ru-PhenISA enters cells via an endocytic pathway and, subsequently, homogeneously diffuse within the cytoplasm across the vesicle membranes.

  DOI：

  10.1021/ic301616b

文献信息

• Luminescent Metal Complexes and Associated Technology
  申请人：Mao Fei

  公开号：US20080145526A1

  公开（公告）日：2008-06-19

  Luminescent metal complexes, methods of producing and/or designing same, methods of using same, and associated technology, are disclosed herein. A luminescent metal complex may be useful for a variety of applications, such as staining, detection, and/or identification, for example, of substances, such as poly(amino acids), for example. Further by way of example, a luminescent metal complex may be useful for staining, detecting, and/or identifying poly(amino acids) that are associated with any of various environments, such as a gel or a gel matrix, such as any associated with SDS-PAGE, for example, a surface environment, such as any associated with western blot, for example, and/or the like. Compositions, solutions, and kits comprising a luminescent metal complex are also disclosed herein.

  本文披露了发光金属配合物的制备和/或设计方法、使用方法以及相关技术。发光金属配合物可以用于各种应用，例如染色、检测和/或识别物质，例如聚（氨基酸）等物质。例如，发光金属配合物可以用于染色、检测和/或识别与各种环境相关的聚（氨基酸），例如凝胶或凝胶基质，例如与SDS-PAGE相关的任何凝胶环境，例如与western blot相关的任何表面环境等等。本文还披露了包含发光金属配合物的组合物、溶液和试剂盒。
• Luminescent metal complexes and associated technology
  申请人：Mao Fei

  公开号：US09193746B2

  公开（公告）日：2015-11-24

  Luminescent metal complexes, methods of producing and/or designing same, methods of using same, and associated technology, are disclosed herein. A luminescent metal complex may be useful for a variety of applications, such as staining, detection, and/or identification, for example, of substances, such as poly(amino acids), for example. Further by way of example, a luminescent metal complex may be useful for staining, detecting, and/or identifying poly(amino acids) that are associated with any of various environments, such as a gel or a gel matrix, such as any associated with SDS-PAGE, for example, a surface environment, such as any associated with western blot, for example, and/or the like. Compositions, solutions, and kits comprising a luminescent metal complex are also disclosed herein.

  本文介绍了荧光金属配合物的制备和/或设计方法，以及使用该配合物的方法和相关技术。荧光金属配合物可用于各种应用，例如染色、检测和/或鉴定物质，例如聚（氨基酸）等物质。例如，荧光金属配合物可用于染色、检测和/或鉴定与各种环境相关的聚（氨基酸），例如凝胶或凝胶基质，例如与SDS-PAGE相关的任何凝胶环境，例如与western blot相关的任何表面环境等。本文还介绍了包含荧光金属配合物的组合物、溶液和试剂盒。
• A Luminescent Poly(amidoamine)–Iridium Complex as a New Singlet-Oxygen Sensitizer for Photodynamic Therapy
  作者：Daniela Maggioni、Marco Galli、Laura D’Alfonso、Donato Inverso、Maria Vittoria Dozzi、Laura Sironi、Matteo Iannacone、Maddalena Collini、Paolo Ferruti、Elisabetta Ranucci、Giuseppe D’Alfonso

  DOI：10.1021/ic502378z

  日期：2015.1.20

  A polymer complex (1(P)) was synthesized by binding bis(cyclometalated) Ir(ppy)(2)(+) fragments (ppy = 2-phenylpyridyl) to phenanthroline (phen) pendants of a poly(amidoamine) copolymer (PhenISA, in which the phen pendants involved similar to 6% of the repeating units). The corresponding molecular complex [Ir(ppy)(2)(bap)](+) (1(M), bap = 4-(butyl-4-amino)-1,10-phenanthroline) was also prepared for comparison. In water solution 1(P) gives nanoaggregates with a hydrodynamic diameter of 30 nm in which the lipophilic metal centers are presumed to be segregated within polymer tasks to reduce their interaction with water. Such confinement, combined with the dilution of triplet emitters along the polymer chains, led to 1(P) having a photoluminescence quantum yield greater than that of 1(M) (0.061 vs 0.034, respectively, in an aerated water solution) with a longer lifetime of the (MLCT)-M-3 excited states and a blue-shifted emission (595 nm vs 604 nm, respectively). NMR data supported segregation of the metal centers. Photoreaction of O-2 with 1,5-dihydroxynaphthalene showed that 1(P) is able to sensitize O-1(2) generation but with half the quantum yield of 1(M). Cellular uptake experiments showed that both 1(M) and 1(P) are efficient cell staining agents endowed with two-photon excitation (TPE) imaging capability. TPE microscopy at 840 nm indicated that both complexes penetrate the cellular membrane of HeLa cells, localizing in the perinuclear region. Cellular photodynamic therapy tests showed that both 1(M) and 1(P) are able to induce cell apoptosis upon exposure to Xe lamp irradiation. The fraction of apoptotic cells for 1(M) was higher than that for 1(P) (74 and 38%, respectively) 6 h after being irradiated for 5 min, but cells incubated with 1(P) showed much lower levels of necrosis as well as lower toxicity in the absence of irradiation. More generally, the results indicate that cell damage induced by 1(M) was avoided by binding the iridium sensitizers to the poly(amidoamine).
• Tuning Polyamidoamine Design To Increase Uptake and Efficacy of Ruthenium Complexes for Photodynamic Therapy
  作者：Luca Mascheroni、Maria Vittoria Dozzi、Elisabetta Ranucci、Paolo Ferruti、Valentina Francia、Anna Salvati、Daniela Maggioni

  DOI：10.1021/acs.inorgchem.9b02245

  日期：2019.11.4

  In this work, we report the synthesis of [Ru(phen)(3)(2+)]-based complexes and their use as photosensitizers for photodynamic therapy (PDT), a treatment of pathological conditions based on the photoactivation of bioactive compounds, which are not harmful in the absence of light irradiation. Of these complexes, Ru-PhenISA and Ru-PhenAN are polymer conjugates containing less than 5%, (on a molar basis), photoactive units. Their performance is compared with that of a small [Ru(phen)(3)(2+)] compound, [Ru(phen)(2)BAP](OTf)(2) (BAP = 4-(4'-aminobutyl)-1,10-phenanthroline, OTf = triflate anion), used as a model of the photoactive units. The polymer ligands, PhenISA and PhenAN, are polyamidoamines with different acid-base properties. At physiological pH, the former is zwitterionic, the latter moderately cationic, and both intrinsically cytocompatible. The photophysical characterizations show that the complexation to macromolecules does not hamper the Ru(phen)(3)(2+) ability to generate toxic singlet oxygen upon irradiation, and phosphorescence lifetimes and quantum yields are similar in all cases. All three compounds are internalized by HeLa cells and can induce cell death upon visible light irradiation. However, their relative PDT efficiency is different: the zwitterionic PhenISA endowed with the Ru-complex lowers the PDT efficiency of the free complex, while conversely, the cationic PhenAN boosts it. Flow cytometry demonstrates that the uptake efficiency of the three agents reflects the observed differences in PDT efficacy. Additionally, intracellular localization studies show that while [Ru(phen)(2)BAP](OTf)(2) remains confined in vesicular structures, Ru-PhenISA localization is hard to determine due to the very low uptake efficiency. Very interestingly, instead, the cationic Ru-PhenAN accumulates inside the nucleus in all treated cells. Overall, the results indicate that the complexation of [Ru(phen)(2)BAP](OTf)(2) with a cationic polyamidoamine to give the Ru-PhenAN complex is an excellent strategy to increase the Ru-complex cell uptake and, additionally, to achieve accumulation at the nuclear level. These unique features together make this compound an excellent photosensitizer with very high PDT efficiency.
• US9193746B2
  申请人：——

  公开号：US9193746B2

  公开（公告）日：2015-11-24