![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 academic research and scientific papers
Functionalization of Deutero- and Protoporphyrin IX Dimethyl Esters via Palladium-Catalyzed Coupling Reactions
O'Brien, Jessica M.,Sitte, Elisabeth,Flanagan, Keith J.,Kühner, Hannes,Hallen, Lukas J.,Gibbons, Dáire,Senge, Mathias O.
, p. 6158 - 6173 (2019)
Herein, we report the functionalization of the β-positions of deutero- and protoporphyrin IX dimethyl esters. Initial halogenations were carried out on both deutero- and protoporphyrin IX dimethyl esters. Although previously reported, vastly optimized yields with respect to deuteroporphyrin halogenation were obtained. Methods were developed for the bromination of the vinyl groups of protoporphyin IX dimethyl ester. Subsequent palladium-catalyzed coupling reactions were utilized to modify the periphery of these naturally occurring porphyrin derivatives with a variety of functionalities. The described Suzuki, Sonogashira, and "Click" reactions demonstrate the ease at which these porphyrins may be manipulated and even interchangeable, as will be discussed for one example. X-ray crystallographic analysis successfully determined the structure of two derivatives synthesized. Results identified a unique head-to-tail stacking pattern for 3,8-diphenyldeuteroporphyrin IX dimethyl ester, most likely due to the presence of additional aromatic moieties on the periphery of the porphyrin.
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.
Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy
Sylvain,Zerrouki,Granet,Huang,Lagorce,Guilloton,Blais,Krausz
, p. 57 - 69 (2002)
The aim of this work is the synthesis of a new family of glycosylated poryphrins in which the sugar moieties are linked to the tetrapyrrole ring by a thioglycosidic bond. Two series have been designed. The first one corresponds to meso-aryl porphyrin derivatives. The second one has been obtained from protoporphyrin IX derivatization. Aryl-porphyrins were prepared from tristolyl o- and p-hydroxyporphyrins followed by bromoallylation and thioglycosylation with peracetylated S-glucose, mannose and galactose and deprotection. The other series has been synthesized from protoporphyrin IX dimethylester with a regioselective glycosylation of terminal alkenyl carbon. The UV-visible, NMR and MALDI mass spectra are presented. Photocytotoxicities of the synthesized compounds against K562 chronic leukaemia cell line has been evaluated. Synthesis and biological evaluation of the following porphyrins. Copyright
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
Albumin aggregation promoted by protoporphyrin in vitro
Gubarev, Yury A.,Kiselev, Aleksey N.,Lebedeva, Natalya Sh.,Syrbu, Sergey A.,Yurina, Elena S.
, p. 211 - 213 (2020)
Protoporphyrin upon its binding with serum albumin changes its secondary structure due to the conversion of part of α helices into β-folding. This process results in the association of albumin globules in vitro.
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.
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.
Syntheses, stability, and tumorcidal activity of porphyrin dimers and trimers with ether linkages
Pandey, Ravindra K.,Shiau, Fuu-Yau,Medforth, Craig J.,Dougherty, Thomas J.,Smith, Kevin M.
, p. 7399 - 7402 (1990)
The first syntheses of a series of regiochemically pure porphyrin dimers and trimers with ether linkages which are structurally related to Photofrin-II are described. Stability of these oligomers was investigated using variable temperature proton NMR spectroscopy, and preliminary biological results reveal that manupulation of peripheral substituents causes a remarkable difference in photosensitizing ability in vivo.
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.
Synthesis of protoporphyrin-lipids and biological evaluation of micelles and liposomes
Tachikawa, Shoji,El-Zaria, Mohamed E.,Inomata, Ryu,Sato, Shinichi,Nakamura, Hiroyuki
, p. 4745 - 4751 (2014)
Protoporphyrin IX (PPIX) lipids were synthesized by introducing a long alkyl chain, such as C13, C15, and C17, at each vinyl group on PPIX via hydrobromination. The PPIX lipids exhibited a water-soluble property by forming their micelles in water and the PPIX-lipid micelles showed relatively low cytotoxicity toward HeLa cells (IC50 = 151.7-379.9 μM) without light irradiation. PL-C17 liposomes (post-inserted liposomes) were readily prepared by adding PL-C17 micelle solution to the liposome solution. The IC 50 values of PPIX, PL-C17 micelles, and PL-C17 liposomes toward HeLa cells were 0.53, 5.65, and 12.9 μM, respectively, after irradiation with a xenon lamp in the 400-800 nm range for 2 min. PL-C17 liposomes were selectively accumulated in the Golgi apparatus in cells.
