CAS: 19660-77-6; (7S,8S)-7-(2-Carboxyethyl)-5-(Carboxymethyl)-18-Ethyl-2,8,12,17-Tetramethyl-13-Vinyl-7H,8H-Porphyrin-3-Carboxylic Acid

该化合物是一种叶绿素衍生光敏剂,广泛用于光动疗法和生物医学研究,其主要优点包括红区吸收高峰(~660纳米),能够深入组织,高单氧量产量,确保有效的光动活动.该化合物显示低暗毒性,从正常组织中快速清除,加强其治疗选择性.氯e6在结构上也可变,允许药物运载系统中量身定制配方.其稳定性,水溶性以及与各种载体的兼容性使它成为癌症治疗,抗微生物疗法和诊断成像方面的多种应用剂.

结构式图片

相似化合物

15664-29-6 149402-51-7 553-12-8

欧盟法规

ECHA物质C&L通报REACH预注册

合成工艺路线路线简述

  • 合成目标产物 Chlorin E6 主要起始原料 Pheophorbide A
  • (文献来源)合成步骤主要原料 Pheophorbide A

专利信息


专利号:US-10919904-B2
优先权日:2016-08-17
标 题 :Northern-southern route to synthesis of bacteriochlorins
发明人:LIU YIZHOU; LINDSEY JONATHAN S; ALLU SRINIVASA RAO; FUJITA HIKARU
权利人:UNIV NORTH CAROLINA STATE
摘要:Described herein are chlorins, bacteriochlorins, methods and intermediates for the synthesis of bacteriochlorins, and methods of using such bacteriochlorins for, among other things, diagnostic and therapeutic purposes such as luminescent compounds in flow cytometry, and as active agents in photodynamic therapy (PDT).

专利号:US-8877171-B2
优先权日:2010-02-03
标 题 :Polyanionic multivalent macromolecules for intracellular targeting of proliferation and protein synthesis
发明人:LICHA KAI; SCHIRNER MICHAEL; WELKER PIA; HAAG RAINER; WEINHART MARIE; PAULUS FLORIAN
权利人:LICHA KAI; SCHIRNER MICHAEL; WELKER PIA; HAAG RAINER; WEINHART MARIE; PAULUS FLORIAN; MIVENION GMBH
摘要:The present invention relates generally to methods and compositions for targeting of intracellular molecules involved in proliferation and protein synthesis of activated cells using polyanionic multivalent macromolecules. In particular aspect, multiple sulfate groups linked to polyol are specifically targeted to the cytoplasm and nucleus of proliferating and activated cells. The invention further comprises novel polyanionic macromolecular compounds and formulations.

专利号:US-5864035-A
优先权日:1996-03-08
标 题:Synthesis of isoimide of chlorins and bacteriochlorins and their use for diagnosis and treatment of cancer
发明人:PANDEY RAVINDRA K; KOZYREV ANDREI N; DOUGHERTY THOMAS J
权利人:HEALTH RESEARCH INC
摘要:Compounds having utility as light absorbing compounds, especially in the area of photodynamic therapy. Such compounds have the formula: ##STR1## where z is â•?O or NR 14 ; R 14 is alkyl or substituted alkyl; R 1 is an amino acid group, a polyamine group, a polyether group or OR 13 where R 13 is alkyl; R 4 through R 11 are --H, --OH alkyl, alkoxy, alkenyl, alkylene, aryl, or aryloxy, or a carbonyl containing group, wherein carbon containing groups may be substituted with carbonyl, hydroxy, phosphoro, carboxy, halo, sulfo, amino and ether substituents, provided that; R 4 may be taken together with R 7 to form â•?O; R 8 may be taken together with R 9 to form â•?O; R 10 may be taken together with R 11 to form â•?O; and R 4 and R 7 may together form a chemical bond and R 8 and R 11 may together form a chemical bond; and R 12 is hydrogen or lower alkyl; provided that if one z is O, the other z is --NR 14 .

专利号:US-5866335-A
优先权日:1994-06-24
标题:Preparation of derivatized 10,10'-substituted-9,9'-biacridine luminescent molecules and signal solutions
发明人:KATSILOMETES GEORGE W; HO PAK T
权利人:KATSILOMETES GEORGE W
摘要:The synthesis of 10,10'-substituted-9,9'-biacridine molecules and their derivatives is disclosed. These molecules are shown to catalyze the production of light by chemiluminescence in the presence of a signal solution having at a pH from about 10.0 to about 14.0, at a concentration effective for producing a chemiluminescent signal, a chelating agent, a sulfoxide, a reducing sugar, an oxidant or combination of oxidants, an alcohol and aqueous sodium tetraborate. These 10,10'-substituted-9,9'-biacridines are used alone or attached to haptens or macromolecules and are utilized as labels in the preparation of chemiluminescent, homogeneous or heterogeneous assays. They are also used in conjunction with other chemiluminescent label molecules to produce multiple analyte chemiluminescent assays.

专利号:US-2002137901-A1
优先权日:2001-01-22
标题:Synthesis, and photodynamic therapy-mediated anti-cancer, and other uses of chlorin e6-transferrin
发明人:CAVANAUGH PHILIP GERARD
摘要:The invention describes the synthesis and proposed usage of a tumor-specific, site-specific tumor cell-killing agent. The agent binds to tumor cells with high affinity and at the same time will bind minimally to surrounding normal cells. The agent has conjugated to it a porphyrin, which when exposed to light, generates cell-killing reactive oxygen species. Thus, in areas which can be irradiated by light, a site-specific, tumor-specific cell killing can occur. The agent consists of the iron-transport protein transferrin (Tf) which is conjugated with the porphyrin chorin e6 (Ce6). For this patent, a novel method of conjugation was developed as conventional methods of conjugation of chlorin e6 to the protein resulted in the loss of transferrin's biological activity. The new conjugation procedure results in the covalent attachment of chlorin e6 to transferrin and yet maintains the natural activity of the protein. The synthesis occurs while the protein is immobilized to QAE-sephadex, in the presence of the zwitterionic detergent CHAPS (3-[(3-cholidamidopropyl) dimethylammonio]- 1 -propanesulfonate). Using this technique, the biological activity of the conjugated transferrin is preserved, the conjugate binds to cell surface transferrin receptors and promotes the growth of cells in culture, all while carrying the cell-killing chlorin e6. The conjugate induces a light-exposure dependent killing of tumor cells in tissue culture. After injection into cancer patients, a tumor cell killing effect will hypothetically be achieved by irradiation of the tumor site with light. The patent covers the new-found synthesis technique for and the in vitro and in vivo tumor cell killing usage of chlorin e6-transferrin.

专利号:US-2019256521-A1
优先权日:2016-08-17
标题:Northern-southern route to synthesis of bacteriochlorins
上海凌凯医药科技有限公司
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主要参考文献

Review papers:
1: Kruczek-Kazibudzka A, Lipka B, Fiegler-Rudol J, Tkaczyk M, Skaba D, Wiench R. Toluidine Blue and Chlorin-e6 Mediated Photodynamic Therapy in the Treatment of Oral Potentially Malignant Disorders: A Systematic Review. Int J Mol Sci. 2025 Mar 12;26(6):2528. doi: 10.3390/ijms26062528.
2: Yu H, Huang Z, Wu J, Zhao Z, Hua Y, Yang Y. Chlorin e6: a promising photosensitizer of anti-tumor and anti-inflammatory effects in PDT. Nanomedicine (Lond). 2025 Feb;20(4):389-400. doi: 10.1080/17435889.2025.2456450. Epub 2025 Jan 29.
3: Hak A, Ali MS, Sankaranarayanan SA, Shinde VR, Rengan AK. Chlorin e6: A Promising Photosensitizer in Photo-Based Cancer Nanomedicine. ACS Appl Bio Mater. 2023 Feb 20;6(2):349-364. doi: 10.1021/acsabm.2c00891. Epub 2023 Jan 26. 20(2):875-885. doi: 10.1021/acs.molpharmaceut.2c00824. Epub 2023 Jan 23. 26(17):8640. doi: 10.3390/ijms26178640.

合成参考文献


参考文献:10.1016/s0166-0934(99)00041-5
摘要:Jiang S, Lin K, Zhang L, Debnath AK. A screening assay for antiviral compounds targeted to the HIV-1 gp41 core structure using a conformation-specific monoclonal antibody. J Virol Methods. 1999 Jun;80(1):85–96. doi: 10.1016/s0166-0934(99)00041-5.
参考文献:10.1021/acs.jmedchem.0c00882
摘要:Yu Z, Zhou J, Ji X, Lin G, Xu S, Dong X, Zhao W. Discovery of a Monoiodo Aza-BODIPY Near-Infrared Photosensitizer: in vitro and in vivo Evaluation for Photodynamic Therapy. J Med Chem. 2020 Sep 10;63(17):9950–64. doi: 10.1021/acs.jmedchem.0c00882.
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