105615-55-2Relevant articles and documents
Newly Synthesized Lipid–Porphyrin Conjugates: Evaluation of Their Self-Assembling Properties, Their Miscibility with Phospholipids and Their Photodynamic Activity In Vitro
Massiot, Julien,Rosilio, Véronique,Ibrahim, Nada,Yamamoto, Akihisa,Nicolas, Valérie,Konovalov, Oleg,Tanaka, Motomu,Makky, Ali
, p. 19179 - 19194 (2018)
Lipid–porphyrin conjugates are considered nowadays as promising building blocks for the conception of supramolecular structures with multifunctional properties, required for efficient cancer therapy by photodynamic therapy (PDT). The synthesis of two new lipid–porphyrin conjugates coupling pheophorbide-a (Pheo-a), a photosensitizer derived from chlorophyll-a, to either chemically modified lyso-phosphatidylcholine (PhLPC) or egg lyso-sphingomyelin (PhLSM) is reported. The impact of the lipid backbone of these conjugates on their self-assembling properties, as well as on their physicochemical properties, including interfacial behavior at the air/buffer interface, fluorescence and absorption properties, thermotropic behavior, and incorporation rate in the membrane of liposomes were studied. Finally, their photodynamic activity was evaluated on esophageal squamous cell carcinoma (ESCC) and normal esophageal squamous epithelium cell lines. The liposome-like vesicles resulting from self-assembly of the pure conjugates were unstable and turned into aggregates with undefined structure within few days. However, both lipid–porphyrin conjugates could be efficiently incorporated in lipid vesicles, with higher loading rates than unconjugated Pheo-a. Interestingly, phototoxicity tests of free and liposome-incorporated lipid–porphyrin conjugates demonstrated a better selectivity in vitro to esophageal squamous cell carcinoma relative to normal cells.
SPHINGOMYELIN, INTERMEDIATES THEREOF AND METHODS FOR PREPARATION OF SAME
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Page/Page column 20-21, (2010/02/13)
The invention concerns novel oxazaphospholanes, cyclic and acyclic, and to their use in the synthesis of sphingomyelin and sphingomyelin analogous as well as to synthetic sphingomyelins obtained therefrom. One group of oxazaphospholane according to the invention has the general formula (1) disclosed herein. Specifically, the invention provides the 2S, 3R stereoisomers of the disclosed oxazaphospholanes and sphingomyelins and synthetic methods for their preparation.
Efficient Synthesis of Sphingosine-1-phosphate, Ceramide-1-phosphate, Lysosphingomyelin, and Sphingomyelin
Kratzer, Bernd,Schmidt, Richard R.
, p. 957 - 964 (2007/10/02)
Readily available D-erythro-azidosphingosine is transformed into 3-O-silyl-protected derivative 6.Reduction of the azido group afforded 3-O-silyl-protected sphingosine 7 which was either converted into N-Fmoc-protected derivative 8 or via N-acylation into ceramide derivatives 16 and 17, respectively.Treatment of 6, 8, and 16 with bis(2-cyanoethoxy)(diisopropylamino)phosphane as monofunctional phsophitylating agent, subsequent oxidation and then removal of the protective groups furnished azidosphingosine-1-phosphate (11), sphingosine-1-phosphate (2), and ceramide-1-phosphate (4), respectively.Treatment of 8 and 17 with bis(diisopropylamino)(2-cyanoethoxy)phosphane as bifunctional phosphitylating agent and then with choline afforded after oxidation and subsequent deprotection lysosphingomyelin (3) and sphingomyelin (1), respectively in high overall yields.All final products are sterochemically pure and possess D-erythro configuration in the sphingosine moiety. - Key Words: Phosphosphingolipids, synthesis of/ Azidosphingosine/ Azidosphingosine-1-phosphate/ Phosphitylation/ Sphingosine phosphates
