5-aminolevulinic acid cyclohexyl ester hydrochloride | 321837-79-0

• 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: 5-aminolevulinic acid cyclohexyl ester hydrochloride
• 英文别名: cyclohexyl 5-amino-4-oxopentanoate Hydrochloride；cyclohexyl 5-amino-4-oxopentanoate;hydrochloride
• CAS: 321837-79-0
• 化学式: C₁₁H₁₉NO₃*ClH
• 分子量: 249.738
• InChiKey: VZTILHVPOPQLJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  69.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氨基乙酰丙酸 、 环己醇 在 氯化亚砜 作用下， 反应 5.0h， 生成 5-aminolevulinic acid cyclohexyl ester hydrochloride
  参考文献：
  名称：

  The Effects of 5-Aminolevulinic Acid Esters on Protoporphyrin IX Production in Human Adenocarcinoma Cell Lines¶

  摘要：

  Photodynamic diagnosis (PDD) and photodynamic therapy (PDT) using 5-aminolevulinic acid (ALA)-induced protoporphyrin IX (PPIX) is an interesting approach to detect and treat dysplasia and early cancers in the gastrointestinal tract. Because of low lipophilicity resulting in poor penetration across cell membranes, high doses of ALA should be administered in order to reach clinically relevant levels of PPIX. One way of increasing PPIX accumulation is derivatization of ALA into a more lipophilic molecule. In our in vitro study, different esterifications of ALA were investigated to analyze the effects on PPIX accumulation in human adenocarcinoma cell lines. For systematic analysis of cell type-specific PPIX accumulation, three human adenocarcinoma cell lines (SW480, HT29 and CaCo2) and a fibroblast cell line (CCD18) were tested. 3-(4,5-Dimethylthiazole-2-yl)-2,5-biphenyl tetrazolium bromide (MTT) assays were performed to ensure that the ALA esters showed no cellular dark toxicity. Different concentrations (ranging from 0.012 to 0.6 mmol/L, 3 h) and incubation times (5, 10, 30, 180 min; 0.12 mmol/L) were examined. PPIX accumulation was measured using flow cytometry. ALA esters, especially ALA-hexylester and ALA-benzylester, induced significant higher PPIX levels in adenocarcinoma cell lines when compared with ALA and may be promising candidates for PDT and PDD.

  DOI：

  10.1562/0031-8655(2001)074<0721:teoaae>2.0.co;2

文献信息

• Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy
  申请人：——

  公开号：US20040106679A1

  公开（公告）日：2004-06-03

  The invention provides compounds for use in photochemotherapy or diagnosis, said compounds being branched alkyl esters or substituted alkyl esters of 5-aminolevulinic acid, or derivatives or pharmaceutically acceptable salts thereof. In particular, the invention provides compounds of formula (I): R 2 2 N—CH 2 COCH 2 CH 2 CO—OR 1 (wherein R 1 represents an optionally substituted branched alkyl (e.g. C 5-30 alkyl) group, or a substituted alkyl group; R 2 , each of which may be the same or different, represents a hydrogen atom or an optionally substituted alkyl group, preferably a group R 1 ; wherein said substituents are selected from hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, amino, aryl, nitro, oxo, fluoro, —SR 3 , —NR 3 2 and PR 3 2 groups, and each alkyl group is optionally interrupted by one or more O—, —NR 3 —, —S— or —PR 3 — groups; and R 3 represents a hydrogen atom or a C 1-6 alkyl group) and salts thereof for use in diagnosis and photochemotherapy of disorders of abnormalities of external or internal surfaces of the body, and products and kits for performing the invention.

  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。
• 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 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。
• ESTERS OF 5-AMINOLEVULINIC ACID AS PHOTOSENSITIZING AGENTS IN PHOTOCHEMOTHERAPY
  申请人：Photocure ASA

  公开号：EP1313695B1

  公开（公告）日：2006-12-27
• US6992107B1
  申请人：——

  公开号：US6992107B1

  公开（公告）日：2006-01-31