![3,8-di[1-(2-hydroxyethyloxy)-2-iodo]ethyldeutero-porphyrin IX dimethyl ester](http://file1.lookchem.com/cas/reactions/2021/08/19/33055616.svg+xml_ms)
5522-66-7Relevant articles and documents
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Clezy,Fookes
, p. 217,218,219,220 (1977)
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NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY OF PETROPORPHYRINS Self-Aggregation Effects, Nuclear Overhauser Enhancements, and Spin-Lattice Relaxation used in Structural Elucidation
Krane, Jostein,Skjetne, Tore,Telnaes, Nils,Bjoroy, Malvin,Solli, Hauk
, p. 4109 - 4120 (1983)
The substitution pattern of the two major petroporphyrins of Marl Slate, the ETIO III and the C32 DPEP, is determined by NMR spectroscopy alone, using self-aggregation effects, nuclear Overhauser enhancements and spin-lattice relaxation times.Protoporphyrin IX dimethyl ester was used as a model compound.
Microwave-Assisted Synthesis of α-Amino Phosphonates Derived from Formylporphyrins of Natural Origin
Pavlov, Vsevolod Yu.,Kabachnik, Maria M.,Zobnina, Elena V.,Timofeev, Vladimir P.,Konstantinov, Igor O.,Kimel, Boris G.,Ponomarev, Gelii V.,Beletskaya, Irina P.
, p. 2193 - 2197 (2003)
The first synthesis of α-amino phosphonates comprising porphyrin core was accomplished. Three methods of obtaining α-amino phosphonates 5-8 were compared. Conventional heating of formylporphyrins 1-4 with r-BuNH 2 and (EtO)2P(O)H in
Photophysical properties of porphyrin derivatives: Influence of the alkyl chains in homogeneous and micro-heterogeneous systems
Santos, Sandra Cruz Dos,Moreira, Leonardo Marmo,Novo, Diogo La Rosa,Santin, Luiza Rosimeri Romano,Bianchini, Daniela,Bonacin, Juliano Alves,Romani, Ana Paula,Fernandes, Adjaci Uchoa,Baptista, Mauricio S.,De Oliveira, Hueder Paulo Moises
, p. 920 - 933 (2015)
This work is focused on the evaluation of the photophysical properties of protoporphyrin-IX derivatives with different alkyl chains. The goal of this work is to understand the physicochemical properties and select prototypes of photosensitizers for photodynamic therapy. Solvents with different dielectric constants were used to obtain relevant data on different physical and chemical processes, such as fluorescence quantum yield and emission level of aggregation in nonpolar media. In addition, studies were conducted in micro-heterogeneous systems through the interaction of porphyrin derivatives with different surfactants, such as cetyltrimethylammonium bromide, sodium dodecyl sulfate and octyl phenol ethoxylate. The compounds were characterized by electronic absorption spectroscopy in the ultraviolet-visible region and fluorescence emission spectroscopy. The comparative study between the different chemical environments evaluated in the present study represents a relevant contribution to the comprehension of the properties acquired by the porphyrins in different micro-heterogeneous systems, which allows us to understand various interactions that these compounds are subject in biological medium, such as the influence of the polarity of the medium in the reactivity of porphyrins with nonpolar substituents. These results show the decisive physicochemical influence of the alkyl chains on the properties of the tetraazomacrocycle porphyrin.
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Battersby et al.
, p. 441 (1973)
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Light harvesting in silicon(111) surfaces using covalently attached protoporphyrin IX dyes
Alderman, Nicholas,Danos, Lefteris,Fang, Liping,Grossel, Martin C.,Markvart, Tom
, p. 12120 - 12123 (2017)
We report the photosensitization of crystalline silicon via energy transfer using covalently attached protoporphyrin IX (PpIX) derivative molecules at different distances via changing the diol linker to the surface. The diol linker molecule chain length was varied from 2 carbon to 10 carbon lengths in order to change the distance of PpIX to the Si(111) surface between 6 ? and 18 ?. Fluorescence quenching as a function of the PpIX-Si surface distance showed a decrease in the fluorescence lifetime by almost two orders of magnitude at the closest separation. The experimental fluorescence lifetimes are explained theoretically by a classical Chance-Prock-Silbey model. At a separation below 2 nm, we observe for the first time, a F?rster-like dipole-dipole energy transfer with a characteristic distance of R0 = 2.7 nm.
Induction of aminolevulinic acid synthase gene expression and enhancement of metabolite, protoporphyrin IX, excretion by organic germanium
Nakamura, Takashi,Saito, Miki,Shimada, Yasuhiro,Fukaya, Haruhiko,Shida, Yasuo,Tokuji, Yoshihiko
, p. 75 - 81 (2011)
Poly-trans-[(2-carboxyethyl) germasesquioxane], Ge-132 is a water-soluble organic germanium compound. Oral intake of dietary Ge-132 changes fecal color and we attempted to identify the fecal red pigment, which increased by the intake of dietary Ge-132. Sprague Dawley rats were given diets containing Ge-132 from 0 to 0.5% concentration. Fecal red pigment was extracted and purified for optical and structural studies. We examined the fecal red pigment content by high performance liquid chromatography (HPLC), and hepatic gene expressions relating to heme synthesis by reverse transcription polymerase chain reaction (RT-PCR). The purified red pigment had particular optical characteristics on the ultraviolet (UV)-visible spectrum (Soret band absorbance at 400 nm) and fluorescence emission at 600 nm by 400 nm excitation, and was identified as protoporphyrin IX by LC-MS analysis. Protoporphyrin IX significantly (P 0.05) increased 2.4-fold in the feces by the intake of a 0.5% Ge-132 diet. Gene expression analysis of the liver explained the increase of protoporphyrin IX by dietary Ge-132 as it enhanced (P 0.05) aminolevulinic acid synthase 1 (Alas1), a rate-limiting enzyme of heme synthesis, expression 1.8-fold, but decreased ferrochelatase (Fech) expression 0.6-fold (P 0.05). The results show that the intake of dietary Ge-132 is related to heme metabolism. Because protoporphyrin IX is used to treat chronic hepatitis, Ge-132 may be a beneficial substance to increase protoporphyrin IX in the liver.
Boron-containing protoporphyrin ix derivatives and their modification for boron neutron capture therapy: Synthesis, characterization, and comparative in vitro toxicity evaluation
El-Zaria, Mohamed E.,Ban, Hyun Seung,Nakamura, Hiroyuki
, p. 1543 - 1552 (2010)
A novel series of boronated porphyrins for potential use in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) for tumor suppression is described. Protoporphyrin IX {i.e., bis(α-methyl-β-pen-tylethylether)protoporphyrin IX, and bis(α-methyl-β-dodecanylethylether)protoporphyrin IX} bearing polyhedral borane anions (B12H11SH2-, B12H11NH3-, or B12H11OH2-) were synthesized with reasonable yields. Modification of the protoporphyrin IX structure was achieved by variation of the lengths of the alkyl chains (pentyl and dodecanyl) attached through ether linkages to the former vinyl groups. The goal of this modification was to develop boronated porphyrins with chemical and physical properties that differed from those of protoporphyrin IX. Performance of an MTT assay with each derivative revealed that the synthesized boronated porphyrins showed low cytotoxicities in a variety of cancer cells. Of these compounds, B12H11NH22--conjugated porphyrin induced a significant increase in the level of boron accumulation and PDT efficacy against HeLa cells.
Development of the sensitizer for generating higher-energy photons under diluted condition via the triplet-triplet annihilation-supported upconversion
Tanaka, Kazuo,Ohashi, Wataru,Inafuku, Kenichi,Shiotsu, Shohei,Chujo, Yoshiki
, (2019/08/26)
It was previously reported that photon upconversion can occur in the solution containing anthracene and the Pt complex of octaethylporphyrin (PtOEP) via the triplet-triplet annihilation process. In this study, by employing the modified Pt complex of the dual anthracene-tethered porphyrin, DA-PtP as a sensitizer, it is demonstrated that shorter-wavelength light can be generated under diluted condition. We synthesized DA-PtP and compared upconversion properties by changing the type of sensitizers. Accordingly, it was shown that the photon upconversion proceeded with the xenon lamp (540 nm) in the presence of DA-PtP. Furthermore, it was found that the emission band in the shorter wavelength light in the near UV region was observed from the solution containing DA-PtP even under diluted condition. From the mechanistic investigation, it was proposed that the anthracene moieties in DA-PtP might inhibit to form agglomeration with the free anthracene. As a result, reabsorption of the higher-energy light generated from upconversion could be suppressed.
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.
