19660-77-6Relevant articles and documents
A simple route to photodynamic chlorin e6 amide derivatives
Chen, Yang,Terazono, Yuichi,Fefer, Michael,Liu, Jun,Gale, Cody B.,Brook, Michael A.
, p. 56 - 64 (2021/07/31)
Amide derivatives of the porphyrin Ce6 have demonstrated efficacy for antimicrobial photodynamic therapy or inactivation of microorganisms. Traditional methods for their synthesis involve carbodiimide coupling agents for direct coupling or, as a more attractive option, to make key mono- and dianhydrides that are then able to react with a variety of nucleophiles. We report a process to efficiently create a Ce6 dianhydride by the simple expedient usage of acetic anhydride as both dehydrating agent and reagent. The dianhydride reacts to give mixtures of mono- and di-amide derivatives. While these are difficult to separate from each other, this route avoids the more difficult challenge of removing unreacted Ce6 from reaction mixtures. The process further avoids the need to separate undesired by-products arising from carbodiimides and provides additional benefits, as it was optimized for use with the greener solvent Cyrene.
Novel chlorin e4 derivative, pharmaceutically acceptable salt thereof, and preparation methods and application of novel chlorin e4 derivative and thepharmaceutically acceptable salt thereof
-
Page/Page column 14, (2021/10/27)
The invention belongs to the technical field of medicines, and relates to a novel chlorin e4 derivative and pharmaceutically acceptable salts thereof, and preparation methods and application of the novel chlorin e4 derivative and thepharmaceutically acceptable salt thereof. The chlorin e4 derivative comprises a structure shown as a general formula I and an optical isomer contained in the structural general formula I; according to the preparation method, 17-propionyl or 13-formyl in chlorin e4 and amino acid are subjected to peptide formation and/or 3-vinyl etherification. The chlorin e4 derivative and the pharmaceutically acceptable salt thereof can be applied as a photodynamic antitumor drug. Compared with the existing similar photosensitizer talaporfin which is clinically applied, the chlorin e4 derivative disclosed by the invention has the advantages of strong photodynamic antitumor activity, high dark toxicity-light toxicity ratio and the like; the derivative can be used for preparing novel photodynamic antitumor drugs including photodynamic cancer treatment drugs, drugs for photodynamic treatment of benign vascular diseases such as age-related macular degeneration and nevus flammeus and drugs for photodynamic treatment of condyloma acuminata.
Anti-tumor evaluation of a novel methoxyphenyl substituted chlorin photosensitizer for photodynamic therapy
Cao, Lei,Dong, Yi,Li, Guangzhe,Li, Yueqing,Wang, Liu,Zhao, Weijie
, (2020/09/16)
Photodynamic therapy (PDT) is a non-invasive and innovative therapeutic approach which has been increasingly applied in clinical cancer therapy. As the central element of PDT, the development of novel photosensitizers (PSs) with longer absorption wavelength, proper lipophilic/hydrophilic profiles, target tissue selectivity, and higher photo?/lowest dark-cytotoxicity is a challenging task. Previously, we designed and synthesized a series of novel long-wavelength chlorin e6 (Ce6)-based PSs via introducing aromatic groups to the vinyl of Ce6 skeleton. The new formed compounds with π-extension system exhibited improved photodynamic effects and spectral characteristics. Among these π-conjugated chlorin PSs, (E)-32-(4-methoxyphenyl)-chlorin e6, named A15, was expected to be a potent antitumor candidate as a PDT agent due to its good photobiological properties. Herein, in this work, we evaluated the effectiveness of A15 in cancer PDT. In vitro, a novel rare earth probe, ATTA-Eu3+ was applied to detect the singlet oxygen (1O2) production of A15 in solution and human hepatoma HepG2 cells, respectively. Moreover, A15 exhibited strong phototoxicity and weak dark cytotoxity to HepG2 cells. In H22 tumor bearing mice, A15 showed excellent tumor accumulation ability via i.v. administration and induced tumor regression, followed by laser treatment. These results indicated that A15 is a potential novel π–extension chlorin-type PS for PDT applications.
Synthesis of PSMA-targeted 131- and 152-substituted chlorin e6 derivatives and their biological properties
Suvorov, Nikita V.,MacHulkin, Alexey E.,Ivanova, Anna V.,Popkov, Alexander M.,Bondareva, Elizaveta A.,Plotnikova, Ekaterina A.,Yakubovskaya, Raisa I.,Majouga, Alexander G.,Mironov, Andrey F.,Grin, Mikhail A.
, p. 1030 - 1038 (2018/09/29)
Prostate cancer is an extremely common cancer among older men. Conventional chemotherapy has proven to be not effective enough in battling it due to its high systemic toxicity and low selectivity. An alternative method of cancer treatment known as photodynamic therapy (PDT) has been shown to be effective. It is not without its faults either: one of the issues it's been known to have is the insufficient selectivity of photosensitizer accumulation in tumor tissues. Recent studies, however, seem to indicate that introducing a PSMA-targeted moiety into photosensitizer might prove to be a solution to this problem. The present paper is concerned with synthesis of PSMA-targeted 131- and 152-substituted chlorin e6 conjugates and their biological characteristics. Our data suggests that the developed conjugates show potential as targeted agents for photodynamic therapy.
Regioisomeric synthesis of chlorin-e 6 dimethyl esters and their optical properties
Nagano, Yasunobu,Ogasawara, Shin,Tamiaki, Hitoshi
, p. 1039 - 1046 (2018/11/23)
Chlorin-e6 dimethyl esters possessing a single carboxy group at the 13-, 151-,or 172-position were prepared by chemically modifying chlorophyll-A. These three synthetic regioisomers were fully characterized by their mass, NMR, and visible absorption spectra. Their molecular structures were unambiguously identified by the specific 1H-13C correlation at the 13-, 15-, and/or 17-substituents in their respective HMBC spectra. Methyl esterification of 13/151-COOH and hydrolysis of 13/151-COOMe affected small shifts of the Qy absorption and fluorescence emission maxima in a diluted CH2Cl2 solution, while no substitution effect of 172-COOH/Me was observed.
A novel Chlorin e6 tromethamine salt, synthesis method of the same, and use of the same
-
Paragraph 0081-0093, (2016/10/07)
The present invention refers to novel chlorine e6 tromethamine in salt of the same, and relates to the use and manufacturing method. (by machine translation)
Chlorophyllin derivatives as photosensitizers: Synthesis and photodynamic properties
Uchoa, Adjaci F.,Konopko, Aaron M.,Baptista, Maurício S.
, p. 2615 - 2622 (2016/02/26)
Two new photosensitizers (PSs) derived from copper-chlorophyllin were designed to have excitation wavelengths appropriate for the use in photodynamic therapy (PDT) and to have amphiphilic character with positive charge, which favors binding to cell membranes and walls and the intracellular localization in mitochondria. Herein we describe the synthesis and characterization of several properties of these two new PS, i.e., photophysical (absorption, fluorescence and singlet oxygen emission quantum yields, Ff and F?, respectively), physical-chemical (aggregation) and photobiological (binding, incorporation and cell killing). As expected, the aggregation affected not only the absorption spectra but also lowered considerably the values of φf and φΔ, which could be controlled by the interaction of the PS with aqueous micelles. In vitro studies were performed in cells, mitochondria, and vesicles to determine uptake, membrane binding, cytotoxicity, phototoxicity, and intracellular localization. The positively charged derivatives showed to be considerably more efficient for cell killing than methylene blue.
Methods for Preparing Chlorophyll a and Chlorin e6
-
Page/Page column 6, (2010/05/13)
The present invention relates to a method for preparing chlorophyll-a and chlorin e6. This invention extracts chlorophyll-a by use of undisrupted chlorella cells themselves, thereby preparing chlorin e6 from the chlorophyll-a extract. The high contents of chlorophyll-a may be obtained by the pretreatment procedure of chlorella cells themselves selected in this invention. The present method is performed according to relatively simple procedures, and is suitable in the mass production of chlorin e6.
