乙基5-氨基-4-氧代戊酸酯盐酸盐(1:1) | 183151-37-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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
• 中文名称: 乙基5-氨基-4-氧代戊酸酯盐酸盐(1:1)
• 中文别名: 乙基5-氨基-4-氧代戊酸酯盐酸盐
• 英文名称: 5-aminolevulinic acid ethyl ester hydrochloride
• 英文别名: ethyl 5-aminolaevulinate hydrochloride；Ethyl 5-amino-4-oxopentanoate Hydrochloride；ethyl 5-aminolevulinate HCl salt；ethyl 5-aminolevulinate hydrochloride；ethyl 5-amino-4-oxopentanoate;hydrochloride
• CAS: 183151-37-3
• 化学式: C₇H₁₃NO₃*ClH
• 分子量: 195.646
• InChiKey: MGTYUHPAVHGVQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.28
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  乙基5-氨基-4-氧代戊酸酯盐酸盐(1:1) 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.75h， 生成 Gly-Gly-ALA-OEt trifluoroacetate
  参考文献：
  名称：

  Evaluation of dipeptide-derivatives of 5-aminolevulinic acid as precursors for photosensitizers in photodynamic therapy

  摘要：

  N-terminal-blocked and N-terminal-free pseudo tripeptide Gly-Gly and Gly-Pro derivatives of 5-aminolevulinic acid (ALA) esters were synthesized as potential specific substrates for cellular peptidases and precursors for the production of the photosensitizer protoporphyrin IX (PpIX). These precursors were evaluated using human cell lines of either carcinoma or endothelial origin. N-blocked or N-free dipeptides-ALA-ethyl esters, but not tripeptides-ALA-ethyl esters (or dipeptides-ALA-ethyleneglycols,) were substrates for cellular peptidases and were metabolized to ALA. The precursors were hydrolyzed intracellularly involving serine-proteases and metalloproteases. Cell selectivity for human endothelial or carcinoma cells was observed for some of these dipeptides-ALA. Thus drugs coupled to Gly-Gly-/Gly-Pro-derivatives may selectively target defined cells in human cancer, depending on specific cellular activating pathways expressed by the cells. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00619-3
• 作为产物：
  描述：

  5-氨基乙酰丙酸盐酸盐 以 乙醇 为溶剂， 以1.0 g (85%)的产率得到乙基5-氨基-4-氧代戊酸酯盐酸盐(1:1)
  参考文献：
  名称：

  Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy

  摘要：

  该发明提供了用于光化疗或诊断的化合物，所述化合物为5-氨基丙酸的支链烷基酯或取代烷基酯，或其衍生物或药用可接受的盐。具体而言，该发明提供了式(I)的化合物：R2N—CH2COCH2CH2CO—OR1（其中R1代表可选择取代的支链烷基（例如C5-30烷基）基团，或取代烷基基团；R2，每个可能相同或不同，代表氢原子或可选择取代的烷基基团，优选为基团R1；其中所述取代基被选择自羟基、烷氧基、酰氧基、烷氧羰氧基、氨基、芳基、硝基、氧代、氟代、—SR3、—NR32和PR32基团，每个烷基基团可选择地被一个或多个O—、—NR3—、—S—或—PR3—基团中断；R3代表氢原子或C1-6烷基基团）及其盐，用于诊断和治疗身体外部或内部表面的异常或疾病的光化疗，以及执行该发明的产品和工具包。

  公开号：

  US20040106679A1

文献信息

• NEW ESTERS OF 5-AMINOLEVULINIC ACID AND THEIR USE AS PHOTOSENSITIZING COMPOUNDS IN PHOTOCHEMOTHERAPY
  申请人：Gierskcky E. Karl

  公开号：US20050107471A1

  公开（公告）日：2005-05-19

  The present invention relates to compounds being esters of 5-aminolevulinic acids or pharmaceutically acceptable salts thereof, including compounds of formula (I) R 2 2 N—CH 2 COCH 2 —CH 2 CO—OR 1 (wherein R 1 may represent alkyl optionally substituted by hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, amino, aryl, oxo or fluoro groups and optionally interrupted by oxygen, nitrogen, sulphur or phosphorus atoms; and R 2 represents a hydrogen atom or a group R 1 , and both R 2 groups may be the identical or different), and their use in diagnosis and photochemotherapy of disorders or abnormalities of external or internal surfaces of the body, and products and kits for performing the invention.

  本发明涉及5-氨基戊酸酯化合物或其药学上可接受的盐，包括式(I)的化合物R22N-CH2COCH2-CH2CO-OR1（其中R1可能代表烷基，可选地被羟基，烷氧基，酰氧基，烷氧羰氧基，氨基，芳基，氧化物或氟基取代，并可由氧，氮，硫或磷原子中断; R2表示氢原子或R1基团，且两个R2基团可以相同或不同），以及它们在诊断和光化学治疗身体内外表面的疾病或异常中的应用，以及用于执行本发明的产品和工具包。
• ESTERS OF 5-AMINOLEVULINIC ACID AS PHOTOSENSITIZING AGENTS IN PHOTOCHEMOTHERAPY
  申请人：GIERSKCKY Karl E.

  公开号：US20090280061A1

  公开（公告）日：2009-11-12

  The present invention relates to compounds being esters of 5 -aminolevulinic acids or pharmaceutically acceptable salts thereof, including compounds of formula (I) R22N—CH2COCH2-CH2CO—OR1 (wherein R1 may represent alkyl optionally substituted by hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, amino, aryl, oxo or fluoro groups and optionally interrupted by oxygen, nitrogen, sulphur or phosphorus atoms; and R2 represents a hydrogen atom or a group R1, and both R2 groups may be the identical or different), and their use in diagnosis and photochemotherapy of disorders or abnormalities of external or internal surfaces of the body, and products and kits for performing the invention.

  本发明涉及酯化5-氨基戊酸或其药用可接受盐的化合物，包括式（I）的化合物R22N—CH2COCH2-CH2CO—OR1（其中R1可以代表烷基，其可以被羟基，烷氧基，酰氧基，烷氧羰基氧基，氨基，芳基，氧，氮，硫或磷原子随意替换并随意中断；R2代表氢原子或R1基团，两个R2基团可以相同或不同），以及它们在诊断和光化学疗法中用于治疗身体内部或外部表面的异常或疾病的用途，以及执行本发明的产品和工具包。
• [EN] ESTERS OF 5-AMINOLEVULINIC ACID AS PHOTOSENSITIZING AGENTS IN PHOTOCHEMOTHERAPY<br/>[FR] ESTERS DE L'ACIDE 5-AMINOLEVULINIQUE EN TANT QU'AGENTS PHOTOSENSIBILISANTS EN PHOTOCHIMIOTHERAPIE
  申请人：PHOTOCURE AS

  公开号：WO1996028412A1

  公开（公告）日：1996-09-19

  (EN) The present invention relates to compounds being esters of 5-aminolevulinic acids or pharmaceutically acceptable salts thereof, including compounds of formula (I) R22N-CH2COCH2-CH2CO-OR1, (wherein R1 may represent alkyl optionally substituted by hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, amino, aryl, oxo or fluoro groups and optionally interrupted by oxygen, nitrogen, sulphur or phosphorus atoms; and R2 represents a hydrogen atom or a group R1, and both R2 groups may be the identical or different), and their use in diagnosis and photochemotherapy of disorders or abnormalities of external or internal surfaces of the body, and products and kits for performing the invention.(FR) La présente invention concerne des composés qui sont des esters de l'acide 5-aminolevulinique, ou des sels de ceux-ci, acceptables sur le plan pharmacologique, notamment des composés de la formule (I) R22N-CH2COCH2-CH2CO-OR1 (dans laquelle R1 peut représenter alkyle éventuellement substitué par des groupes hydroxy, alcoxy, acyloxy, alcoxycarbonyloxy, amino, aryle, oxo ou fluoro, et éventuellement interrompu par des atomes d'oxygène, d'azote, de soufre ou de phosphore; et R2 représente un atome d'hydrogène ou un groupe R1, et les deux groupes R2 peuvent être identiques ou différents); l'invention concerne également l'utilisation de ces composés dans le diagnostic et la photochimiothérapie de troubles ou d'anomalies des surfaces externes ou internes du corps; elle concerne encore des produits et des kits permettant sa réalisation.

  本发明涉及5-氨基戊酸酯化合物或其在药学上可接受的盐，包括式(I) R22N-CH2COCH2-CH2CO-OR1的化合物（其中R1可以代表烷基，该烷基可选择地被羟基，烷氧基，酰氧基，烷氧羰基氧基，氨基，芳基，氧化物或氟代基取代，并且可以被氧，氮，硫或磷原子中断; R2表示氢原子或R1基团，且两个R2基团可以相同或不同），以及它们在诊断和治疗身体内外表面的疾病或异常方面的使用，以及用于执行本发明的产品和工具包。
• Esters of 5-aminolevulinic acid and their use as photosensitizing compounds in photochemotherapy
  申请人：Photocure ASA

  公开号：US07287646B2

  公开（公告）日：2007-10-30

  The present invention relates to compounds being esters of 5-aminolevulinic acids or pharmaceutically acceptable salts thereof, including compounds of formula (I) R22N—CH2COCH2—CH2CO—OR1 (wherein R1 may represent alkyl optionally substituted by hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, amino, aryl, oxo or fluoro groups and optionally interrupted by oxygen, nitrogen, sulphur or phosphorus atoms; and R2 represents a hydrogen atom or a group R1, and both R2 groups may be the identical or different), and their use in diagnosis and photochemotherapy of disorders or abnormalities of external or internal surfaces of the body, and products and kits for performing the invention.

  本发明涉及5-氨基戊酸酯或其药学上可接受的盐的化合物，包括式(I)的化合物R22N—CH2COCH2—CH2CO—OR1（其中R1可以表示烷基，该烷基可以选择地被羟基，烷氧基，酰氧基，烷氧羰基氧基，氨基，芳基，氧代，氮代，硫代或磷代原子中断; R2表示氢原子或R1基团，且两个R2基团可以相同或不同），以及它们在诊断和照光治疗身体内外表面的疾病或异常方面的使用，以及执行本发明的产品和工具包。
• Improved Peptide Prodrugs of 5-ALA for PDT: Rationalization of Cellular Accumulation and Protoporphyrin IX Production by Direct Determination of Cellular Prodrug Uptake and Prodrug Metabolization
  作者：Francesca Giuntini、Ludovic Bourré、Alexander J. MacRobert、Michael Wilson、Ian M. Eggleston

  DOI：10.1021/jm900224r

  日期：2009.7.9

  Twenty-seven dipeptide derivatives of general structure Ac-Xaa-ALA-OR were synthesized as potential prodrugs for 5-aminolaevulinic acid-based photodynamic therapy (ALA-PDT). Xaa is an (x-amino acid, chosen to provide a prodrug with appropriately tailored lipophilicity and water solubility. Although no simple correlation is observed between downstream production of protoporphyrin IX (PpIX) in PAM212 keratinocytes and HPLC-derived descriptors of compound lipophilicity, quantification of prodrug uptake reveals that most of the dipeptides are actually more efficiently accumulated than ALA in PAM212 and also A549 and Caco-2 cell lines. Subsequent ALA release is the limiting factor, which emphasizes the importance of decoupling prodrug uptake and intracellular metabolization when assessing the efficacy of ALA derivatives for PDT. In agreement with PpIX fluorescence studies, at,I concentration of 0.1 MM, L-Phe derivatives 4m and 4o, and L-Leu, L-Met, and L-Glu derivatives 4f, 4k, and 4u, exhibit significantly enhanced photoxicity in PAM212 cells compared to ALA.