15592-17-3Relevant articles and documents
Synthesis of new derivatives of protoporphyrin IX and chlorophyll a
Pavlov,Konstantinov,Ponomarev,Timofeev,Kimel'
, p. 1824 - 1835 (2005)
The vinyl groups in protoporphyrin IX and chlorophyll a derivatives were selectively transformed into hydroxymethyl and acetoxymethyl substituents. The reactivities of β-hydroxymethyl and β-acetoxymethyl groups in porphyrins and chlorins toward nucleophilic reagents were compared for the first time using the reaction with acetylacetone as an example. Peripheral acetylacetone moieties in porphyrins and chlorins were shown to be promising as building blocks for generation of exo heterocyclic structures.
Syntheses and cellular investigations of 173-, 152-, and 131-amino acid derivatives of chlorin e6
Jinadasa, R. G. Waruna,Hu, Xiaoke,Vicente, M. Gra?a H.,Smith, Kevin M.
, p. 7464 - 7476 (2011)
A series of amino acid conjugates of chlorin e6, containing lysine or aspartic acid residues in positions 173, 152, or 131 of the macrocycle were synthesized and investigated as photosensitizers for photodynamic therapy of tumors. All three regioisomers were synthesized in good yields and in five steps or less from pheophytin a (1). In vitro investigations using human carcinoma HEp2 cells show that the 15 2-lysyl regioisomers accumulate the most within cells, and the most phototoxic are the 131 regioisomers. The main determinant of biological efficacy appears to be the conjugation site, probably because of molecular conformation. Molecular modeling investigations reveal that the 173-substituted chlorin e6 conjugates are L-shaped, the 152 and 131 regioisomers assume extended conformations, and the 131 derivatives are nearly linear. It is hypothesized that the 131-aspartylchlorin e6 conjugate may be a more efficient photosensitizer for PDT than the commercial currently used 15 2 derivative.
Syntheses of water-soluble cationic porphyrins and chlorins
Pandey,Shiau,Smith,Dougherty,Smith
, p. 7591 - 7600 (1992)
Reactions of vinylchlorins and vinylporphyrins with N,N-dimethylmethyleneammonium iodide ('Eschenmoser's Reagent') gives Mannich adducts in which substitution (with CH2NMe2) has taken place on the terminal carbon of the vinyl group to yield a trans-3-(N,N-dimethylaminomethyl)prop-1-enyl derivative. Under no circumstances was meso substitution observed. Use of zinc(II) vinylchlorins or zinc(II) vinylporphyrins afforded the corresponding zinc(II) trans-vinyl adducts at a significantly faster rate than the metal-free substrates. Reaction of Eschenmosers reagent with deuteroporphyrin-IX dimethyl ester (29) (which possesses two peripherally unsubstituted positions) produces the bis-(N,N-dimethylaminomethyl) product (30). Treatment of the dimethylamino chlorins and porphyrins with methyl iodide, in all cases, gives an excellent yield of the corresponding quaternary ammonium iodides, and these compounds are highly water-soluble.
Mono-(L)-aspartylchlorin-e6
Hargus, Jodie A.,Fronczek, Frank R.,Vicente, M. Graa H.,Smith, Kevin M.
, p. 1006 - 1015 (2007)
Mono-(l)-aspartylchlorin-e6 (also known as Talaporfin, NPe6, MACE, and most recently LS-11) is a potent sensitizer for photodynamic therapy that is currently undergoing clinical trials. Using a combination of unambiguous partial synthesis from pheophytin-a and methyl pheophorbide-a, NMR spectroscopy, and single crystal X-ray diffraction, the structure of mono-(l)-aspartylchlorin-e6 is definitively shown to be the isomer in which the aspartyl residue is attached at the 152-side chain position. This conclusion is contrary to earlier assumptions, but affirms the conclusions of a study based on NMR spectroscopy; a rationale for the unique formation of the 152-aspartyl derivative is proposed.
Chlorophyllin derivatives as photosensitizers: Synthesis and photodynamic properties
Uchoa, Adjaci F.,Konopko, Aaron M.,Baptista, Maurício S.
, p. 2615 - 2622 (2015)
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.
, p. 3661 - 3665 (2015)
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
Chlorin e6 ferrocene conjugate with photo- and acoustic-sensitive activity as well as preparation method and application
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, (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.
