Synthesis and Electropolymerization of Phosphorylcholine-Containing Pyrroles and Their Hemocompatible Properties

A series of N-substituted pyrroles having phosphorylcholine with different methylene chain lengths between pyrrole group and phosphorylcholine group were synthesized and their electropolymerizations were performed in aqueous solution. The methylene chains were trimethylene (n = 3), pentamethylene (n...

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Published inAnalytical Sciences Vol. 26; no. 5; pp. 539 - 543
Main Authors YASUZAWA, Mikito, MATSUKI, Takashi, YAMADA, Tetsuya, KUNUGI, Akira
Format Journal Article
LanguageEnglish
Published Singapore The Japan Society for Analytical Chemistry 2010
Springer Nature Singapore
Japan Science and Technology Agency
Subjects
Analytical Chemistry
Biocompatible Materials - chemical synthesis
Biocompatible Materials - chemistry
Biocompatible Materials - pharmacology
Blood - drug effects
Blood Coagulation - drug effects
Chemistry
Electrochemistry
Humans
Methane - analogs & derivatives
Methane - chemistry
Microscopy, Electron, Scanning
Phosphorylcholine - chemistry
Phosphorylcholine - pharmacology
Platelet-Rich Plasma
Polymers - chemistry
Pyrroles - chemistry
Pyrroles - pharmacology
Solutions - chemistry
Water - chemistry
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Summary:A series of N-substituted pyrroles having phosphorylcholine with different methylene chain lengths between pyrrole group and phosphorylcholine group were synthesized and their electropolymerizations were performed in aqueous solution. The methylene chains were trimethylene (n = 3), pentamethylene (n = 5), nonamethylene (n = 9), and undecamethylene (n = 11), for 3-(1-pyrrolyl)propyl-2-(trimethylammonium)ethyl phosphate (5a), 5-(1-pyrrolyl)pentyl-2-(trimethylammonium)ethyl phosphate (5b), 9-(1-pyrrolyl)nonyl-2-(trimethylammonium)ethyl phosphate (5c), and 11-(1-pyrrolyl)undecyl-2-(trimethylammonium)ethyl phosphate (5d), respectively. Although electropolymerized films were produced from all pyrrole derivatives, thick and black polymer films were prepared from 5a, 5b and 5c. The pyrrole derivative with long methylene-chain 5d provided only colorless or slightly blackish thin film. Hemocompatibilities of the polymers from 5a, 5b and 5c were evaluated by platelet rich plasma (PRP) contacting studies and scanning electron microscopy (SEM) observations. The results indicated that these polymers have excellent hemocompatibility.
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ISSN:0910-6340
1348-2246
DOI:10.2116/analsci.26.539