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.
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.
