10591-31-8Relevant academic research and scientific papers
TARGETED ANTIMICROBIAL PHOTODYNAMIC THERAPY
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Paragraph 0180, (2019/10/29)
The present application relates generally to a method and a composition matter that provides a rapid and potent antimicrobial photodynamic inactivation (aPDI) of pathogenic bacteria that express high-affinity cell-surface hemin receptors (CSHRs) using Ga(III)-protoporphyrins IX (GaPpIX or Ga-PpIX). The invention provides an effective treatment option for infections of skin or body cavities that are accessible to visible-light irradiation, such as a handheld LED array emitting visible light (405 nm), especially for infections caused by Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus (MRSA), pathogenic staphylococci, Streptococcus mutans, S. pneumoniae, S. pyogenes, streptococci, corynebacteria, mycobacteria, and Bacillus anthracis.
Facile iodination of the vinyl groups in protoporphyrin IX dimethyl ester and subsequent transformation of the iodinated moieties
Miyata, Kota,Yasuda, Satoru,Masuya, Takuto,Ito, Satoshi,Kinoshita, Yusuke,Tamiaki, Hitoshi,Oba, Toru
supporting information, p. 3707 - 3711 (2018/05/28)
Iodination of protoporphyrin IX dimethyl ester using phenyliodine bis(trifluoroacetate) (PIFA) and I2 was studied. Iodine added to both the C3- and C8-vinyl groups equally to afford the iodohydrin or iodoether in the presence of water or alcohol, respectively. Any meso-hydrogen atom was not substituted by an iodine atom under these conditions, although both the vinyl group and one of the meso positions of methyl pyropheophorbide-a bearing a chlorin π-system, a chlorophyll-a derivative, was modified with PIFA and I2. The reaction intermediates derived from the porphyrin were more reactive than those from the chlorin and liable to form intermolecular linkages. The obtained 2-iodo-1-hydroxyethyl group was transformed into a formyl group by a mild treatment. The corresponding iodoether moiety was readily converted into the acetyl group under basic conditions. These transformations were also applicable to smaller olefins such as styrene.
Process For Preparing Porphyrin Derivatives, Such As Protoporphyrin (IX) And Synthesis Intermediates
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Page/Page column 13; 20, (2008/12/07)
The present invention relates to a process for preparing a porphyrin of formula (I), optionally in the form of a salt with an alkali metal and/or in the form of a metal complex: in which: R and R′ are as defined in claim 1, comprising: a step of condensation, in an acidic medium, between a dipyrromethane of formula (II): in which R′b is as defined above for (I), and a dipyrromethane of formula (III): in which R″ is as defined in claim 1, and also the compounds of formula (III).
Electronic effects of peripheral substituents at porphyrin meso positions
Zhu, Yaoqiu,Silverman, Richard B.
, p. 233 - 239 (2007/10/03)
Porphyrins are stable molecules with a macrocyclic conjugated system and often peripheral substituents. This unique structure makes the electronic properties of the four meso-carbons (the methine bridges) nearly identical. Replacement of the weakly electron-polarizing 2,4-vinyl groups of protoporphyrin IX with strongly electron-polarizing acetyl groups not only leads to much lower meso-carbon reactivities toward electrophilic aromatic substitution but also results in a significant meso-selectivity (the β- and γ-meso- positions become much more nucleophilic (basic) than the α- and δ-meso-positions). To further investigate the relationship between the porphyrin meso-carbon reactivities and the peripheral substituents, two monoacetylporphyrin analogues also were synthesized. This investigation not only leads to empirical rules for predicting porphyrin meso-carbon selectivities but also provides important models for theoretical calculations of porphyrin aromaticity.
Synthesis of ether- and carbon-linked polycarboranyl porphyrin dimers for cancer therapies
Isaac, Meden F.,Kahl, Stephen B.
, p. 232 - 243 (2007/10/03)
Porphyrin dimers bearing multiple carborane cages for potential use as sensitizers in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) were synthesized from protoporphyrin dimethyl ester and characterized. Diastereomeric ether-linked di
Oxidative rearrangement of acetylporphyrins
Chakrabarty, Manas
, p. 761 - 764 (2007/10/03)
Oxidative rearrangement of 2-/4-monoacetyl- and 2,4-diacetlydeuteroporphyrin IX dimethyl esters by methanolic thallic nitrate trihydrate in presence of conc, nitric acid furnished the corresponding mono- and dimethoxycarbonylmethylporphyrins, respectively.
Synthesis of fluorine analogs of protoporphyrin potentially useful for diagnosis and therapy of cancer. IV. Synthesis of (trifluorovinyl)vinyland (1-chloro-2,2-difluorovinyl)vinyldeuteroporphyrins
Shigeoka, Tsuyoshi,Kuwahara, Yasuhisa,Watanabe, Kiyoko,Sato, Kazuyuki,Omote, Masaaki,Ando, Akira,Kumadaki, Itsumaro
, p. 1326 - 1329 (2007/10/03)
Trifluoro or chlorodifluoro analogs of protoporphyrin, the compounds in the title, were synthesized for use in the diagnosis and therapy of cancer. 3- Or 8-acetyldeuteroporphyrin dimethyl esters (2 and 3) were iodinated with iodine in the presence of potassium carbonate to the corresponding iodo compounds (5 and 6). The iodo compounds (5 and 6) were treated with bis(trifluorovinyl)zinc in the presence of tetrakis(triphenylphosphine)palladium to give trifluorovinyl derivatives (7 and 8) in good yields. Reduction of the acetyl group of 7 and 8 with sodium borohydride afforded the corresponding hydroxyethyl derivatives (9 and 10). Compounds (9 and 10) were dehydrated with methanesulfonyl chloride and triethylamine to give (trifluorovinyl)vinyldeuteroporphyrin dimethyl esters (11 and 12). Treatment of 5 and 6 with bis(1-chloro-2,2-difluorovinyl)zinc in the presence of tetrakis(triphenylphosphine)palladium, followed by similar reactions as above gave (1-chloro-2,2-difluorovinyl)vinyldeuteroporphyrin dimethyl esters (17 and 18).
Porphyrin Dimers as Photosensitizers in Photodynamic Threapy
Pandey, Ravindra K.,Smith, Kevin M.,Dougherty, Thomas J.
, p. 2032 - 2038 (2007/10/02)
Porphyrin dimers 9 with ether linkages and possible isomers bis-1,3,5,8-tetramethyl-2-vinylporphin-4-yl>ethyl> ether (10) bis-1,3,5,8-tetramethyl-4-vinylporphin-2-yl>ethyl> ether (11), and 1--1,3,5,8-tetramethyl-2-vinylporphin-4-yl>ethyl 1--1,3,5,8-tetramethyl-4-vinylporphin-2-yl>ethyl ether (12) were synthesized from the corresponding (1-hydroxyethyl)vinyldeuteroporphyrin IX dimethyl esters (Hvd).The pure Hvd isomers 2-(1-hydroxyethyl)-4-vinyldeuteroporphyrin IX dimethyl ester (7) and 4-(1-hydroxyethyl)-2-vinyldeuteroporphyrin IX dimethyl ester (8) were obtained from 2-acetyl-4-(1-hydroxyethyl)deuteroporphyrin IX dimethyl ester (3) and 4-acetyl-2-(1-hydroxyethyl)deuteroporphyrin IX dimethyl ester (4).Porphyrins 3 and 4 were prepared either by partial reduction of 2,4-diacetyldeuteroporphyrin IX dimethyl ester (2) or by oxidation of hematoporphyrin IX dimethyl ester (1) by using tetra-n-propylammonium perruthenate (Prn4N)(RuO4) with N-methylmorpholine N-oxide as an oxidizing agent.The in vivo photosensitizing ability and therapeutic ratios of dimers 9-12 were compared with that of Photofrin II in the SMT-F tumor growing subcutaneously in DBA/2 Ha mice.These dimers were found to have better tumorcidal activity than Photofrin II with reduced skin phototoxicity.
THE SYNTHESIS OF DIHEMATOPORPHYRIN ETHER AND RELATED PORPHYRIN DIMERS
Morris, Ian K.,Ward, A. David
, p. 2501 - 2504 (2007/10/02)
Dihematoporphyrin ether (DHE) has been synthesised by two separate procedures; these routes also allow the synthesis of ether linked porphyrin dimers containing one or two vinyl groups rather than hydroxyethyl side chains.The latter dimers, but not DHE, have anti-cancer activity.
PARTIAL SYNTHESES OF 1- AND 3-METHYL DEUTERIATED DERIVATIVES OF PROTOPORPHYRIN-IX FROM PROTOHEMIN
Smith, Kevin M.,Leung, Hiu-Kwong,Parish, Daniel W.
, p. 2743 - 2761 (2007/10/02)
Treatment of 2,4-diacetyldeuteroporphyrin-IX dimethyl ester (3) with sodium methoxide in methanol-d affords the 1,3-di-(trideuteriomethyl) derivative in which the acetyl methyls and propionate methylenes adjacent to the ester carbonyl have also been deuteriated.The acetyl methyls and propionates can be back-exchanged under acidic conditions, but the 1- and 3-methyls retain their isotope labeling.Reduction with sodium borohydride, followed by dehydration affords the corresponding 1,3-di-(trideuteriomethyl)-protoporphyrin-IX dimethyl ester (4) with approximately 95percent deuteriation in the methyls.Insertion of iron and hydrolysis affords the corresponding hemin (15), suitable for n.m.r. studies of reconstituted heme proteins.A similar sequence of reactions with 2- and 4- monoacetyldeuteroporphyrins (5) and (6) gives the 1- and 3-(trideuteriomethyl) derivatives and these are, in turn, further acetylated and transformed into the corresponding mono-trideuteriomethylprotoporphyrins (7) and (8), and hemins (22) and (23).
