35038-32-5Relevant academic research and scientific papers
Synthesis and: In vitro phototoxicity of novel π-extension derivatives of chlorin e6
Cao, Lei,Guo, Xiuhan,Wang, Liu,Wang, Shisheng,Li, Yueqing,Zhao, Weijie
, p. 14279 - 14287 (2017)
Six novel E-32-aryl substituted chlorins (5a-5f) were synthesized via improved regioselective bromination and Suzuki-Miyaura cross-coupling reactions with chlorin e6 (1) as a starting material. All the π-extension photosensitizers 5a-5f exhibited significant bathochromic-shifts (ca. 10 nm) in the far red part of the spectrum called the phototherapeutic window and decreased photobleaching under irradiation of 660 nm light. Moreover, 5a-5f possessed higher phototoxicity in vitro against HepG2 cells (IC50 = 0.73 ± 0.04, 2.33 ± 0.22, 0.78 ± 0.05, 0.50 ± 0.04, 2.25 ± 0.16 and 0.65 ± 0.11 μM, respectively) compared with chlorin e6 (IC50 = 28.9 ± 1.2 μM). The enhanced cellular uptake and reactive oxygen species (ROS) production of modified chlorins were found to be responsible for their increased in vitro phototoxicity.
Chlorin e6 ferrocene conjugate with photo- and acoustic-sensitive activity as well as preparation method and application
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Paragraph 0077-0079, (2020/08/07)
The invention provides a chlorin e6 ferrocene conjugate with photo- and acoustic-sensitive activity as well as a preparation method and application thereof, and belongs to the technical field of chemical medicines. The chlorin e6 ferrocene conjugate disclosed by the invention has different degrees of inhibition effects on Hela cells in in-vitro anti-tumor activity evaluation. The introduction of the ferrocene group significantly improves the proliferation inhibition activity of the compound on tumor cells, and the proliferation inhibition activity of the chlorin e6 ferrocene conjugate on tumorcells is much higher than that of chlorin e6 used as a control group. The method can be used for preparing photosensitizers and sonosensitizers in photodynamic therapy and sonodynamic therapy methodsfor tumor therapy.
Chlorin derivative, corresponding preparation method and application thereof
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Paragraph 0255-0259, (2020/11/25)
The invention relates to a chlorin derivative, a preparation method of the chlorin derivative, a photoacoustic sensitive agent containing the chlorin derivative, an antitumor drug containing the chlorin derivative, and application of the chlorin derivative in preparation of the antitumor drug. The chlorin derivative of the present invention can be used for photodynamic therapy and sonodynamic therapy so as to effectively suppress and treat cancer.
PHOTOSENSITIZER COMPOUNDS, METHODS OF MANUFACTURE AND APPLICATION TO PLANTS
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Paragraph 0242-0244, (2020/08/13)
Provided herein are compounds of general Formula I: or agriculturally acceptable salts thereof. The compounds of Formula I can be used to improve the health of plants. For example, the compounds of Formula I can be used to inhibit a microbial pathogen of a plant, or to increase resistance of a plant to one or more abiotic stress. Methods of manufacturing the compounds of general Formula I, as well as synthetic intermediates are also provided.
Functionalization of chlorin e6 trimethylester towards potential amphiphilic photosensitizers for photodynamic therapy
Bauer, Daniela,Nghiem, Hai Vu,Tien, Doan Duy,Stelten, Johannes,Montforts, Franz-Peter
, p. 243 - 250 (2019/02/19)
Chlorins (dihydroporphyrins) are considered, due to their ideal photophysical properties, as attractive photosensitizers for photodynamic therapy (PDT) of cancer and other therapeutic and diagnostic applications. Chlorophyll a, as a naturally occurring chlorin, forms an almost unlimited renewable resource for preparation of potential biologically active chlorin photosensitizers and fluorescence markers. To achieve amphiphilic photosensitizers which might be selectively enriched in tumor cells, we addressed linkage of per se lipophilic chlorophyll derivatives with carbohydrate based hydrophilic aminopolyols.
S,S-Chiral Linker Induced U Shape with a Syn-facial Sensitizer and Photocleavable Ethene Group
Ghosh, Goutam,Belh, Sarah J.,Chiemezie, Callistus,Walalawela, Niluksha,Ghogare, Ashwini A.,Vignoni, Mariana,Thomas, Andrés H.,McFarland, Sherri A.,Greer, Edyta M.,Greer, Alexander
, p. 293 - 305 (2018/10/02)
There is a major need for light-activated materials for the release of sensitizers and drugs. Considering the success of chiral columns for the separation of enantiomer drugs, we synthesized an S,S-chiral linker system covalently attached to silica with a sensitizer ethene near the silica surface. First, the silica surface was modified to be aromatic rich, by replacing 70% of the surface groups with (3-phenoxypropyl)silane. We then synthesized a 3-component conjugate [chlorin sensitizer, S,S-chiral cyclohexane and ethene building blocks] in 5 steps with a 13% yield, and covalently bound the conjugate to the (3-phenoxypropyl)silane-coated silica surface.?We hypothesized that the chiral linker would increase exposure of the ethene site for enhanced?1O2-based sensitizer release. However, the chiral linker caused the sensitizer conjugate to adopt a U shape due to favored 1,2-diaxial substituent orientation; resulting in a reduced efficiency of?surface loading.?Further accentuating the?U shape was π–π stacking between the?(3-phenoxypropyl)silane and sensitizer. Semiempirical calculations and?singlet oxygen luminescence?data provided deeper insight into the sensitizer's orientation and release. This study has lead to insight on modifications of surfaces for drug photorelease and can help lead to the development of miniaturized photodynamic devices.
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.
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.
Chlorin e6 131:152-anhydride: A key intermediate in conjugation reactions of chlorin e6
Chen, Hui,Jinadasa, R. G. Waruna,Jiao, Lijuan,Fronczek, Frank R.,Nguyen, Alex L.,Smith, Kevin M.
supporting information, p. 3661 - 3665 (2015/06/16)
Since the patent for the photodynamic therapy agent Talaporfin (mono-L-aspartylchlorin e6) was issued in 1987, confusion has existed regarding which of the three carboxylic acid groups in the chlorophyll degradation product, chlorin e6/su
Protonation-deprotonation equilibria in tetrapyrroles Part 3. Mono-and diprotonations of the trimethyl esters of chlorin e6 and the 71-acetal of rhodin g7 in methanolic hydrochloric acid
Hynninen, Paavo H.
, p. 1167 - 1176,10 (2012/12/12)
Spectrophotometric protonation titrations were performed for the trimethyl esters (TME) of chlorin e6 (31,32- didehydrorhodochlorin-15-acetic acid) and the 71-acetal of rhodin g7 (31,32-didehydrorhodochlorin-7 1-oxo-15-acetic acid) using HCl as the acid and methanol as the solvent. For rhodin g7 TME, the 71-acetal formation could be clearly detected as the first step in the titration. Only two spectroscopically different protonated species were observed for each chlorin derivative in addition to the neutral forms. The two protonated species were assigned to the monocation and dication of each chlorin derivative. The following pKa values were obtained: pK3 = 4.63 and pK 4 = 0.62 for chlorin e6 TME and pK3 = 4.40 and pK4 = 0.60 for the acetal of rhodin g7 TME. The protonation titration for chlorin e6 TME with HCl in acetic acid afforded UV-vis spectra similar to those obtained with HCl in methanol. The UV-vis spectrometric parameters are given for the neutral forms of chlorin e6 TME, rhodin g7 TME and its 71-acetal, as well as for the mono- and diprotonated species of chlorin e6 TME and rhodin g7 TME acetal. The protonation titration results of the chlorin e6 derivatives are compared with those previously obtained for phytyl/methyl pyropheophorbide a.
