Polymeric phospholipid analogues, 14. The convenient preparation of a vinyl monomer containing a phospholipid analogue

Umeda, Takashi; Nakaya, Tadao; Imoto, Minoru

doi:10.1002/marc.1982.030030701

Cited by 67 publications

(35 citation statements)

References 8 publications

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“…In the present time, the poly(MPC) and water-soluble poly(MPC-co-n-butyl methacrylate (BMA)) do not induce hemolysis of red blood cells (19,20). Since this first report, several researchers have studied the synthesis of MPC and its polymers (21)(22)(23). At that time, the synthesis of the MPC was very difficult because it indicates the hygroscopic character under atmosphere.…”

Section: Monomers Bearing the Pc Groupmentioning

confidence: 96%

Phospholipid Polymers

Ishihara

2012

Encyclopedia of Polymer Science and Technology

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Section: Monomers Bearing the Pc Groupmentioning

confidence: 96%

Phospholipid Polymers

Ishihara

2012

Encyclopedia of Polymer Science and Technology

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“…In 1982 the rst phosphatidylcholine-analogue-containing vinyl monomer, 2-(methacryloyloxy)ethyl-2-(trimethylammonium)ethyl phosphate (MTP) was reported [31]. The structure of MTP is shown in Fig.…”

Section: Phosphatidylcholine-analogue-containing Diolsmentioning

confidence: 99%

“…The synthesis and property investigations of the phosphatidylcholine-analogue-containing polymers and phospholipid polymers are of increasing interest, not only because the famous membrane model of Singer and Nicolson, which pictures a double layer formed by a lipid matrix and proteins, but also because phospholipids are the most abundant among the lipids found in membranes [26]. During the past three decades, several groups focused their interest and attention on the polymerizable phospholipids, e.g., Nakaya et al [27][28][29][30][31][32][33][34][35][36][37][38][39], Regen et al [40][41][42][43], Ringsdorf et al [44][45][46][47][48], Chapman et al [49][50][51][52][53][54][55][56], O'Brien et al [57][58][59], Tsuchida et al [60], Singh et al [61] and Ishihara [62] have incorporated many polymerizable groups into various lipid structures to prepare phospholipid polymers and investigate their properties and potential applications.…”

Section: Aibnmentioning

confidence: 99%

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Recent progress of phospholipid polymers

Nakaya¹,

Li²

2003

Designed Monomers and Polymers

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Since in 1982 the rst phosphatidylcholineanalogues-containingvinyl monomer 2-(methacryloyloxy)ethyl-2-(trimethylammonium)ethyl phosphate (MTP) was reported, more and more attention has focused on its polymers, as phospholipid polymers have been found to show excellent biocompatibility. We reviewed the progress of phospholipid polymers in 1997 which covered literature from 1974 to 1997; and mainly focused on phosphatidylcholineanalogues-containingvinyl polymers. This review re ects mainly recent research (i.e., mostly later than 1997) and important development progress on polymeric polyphospholipid analogues. A variety of approaches for design, synthesis, characterization, property investigation and potential applications for phospholipid-analoguecontaining polyurethanes and 2-methacryloyloxyethylphosphorylcholine-containing polymers have been extensivelydiscussed. The polymeric phospholipid analogues include polymers such as side-and main-chain types of phosphatidylcholine-analogue-containing polyurethanes, side-and main-chain types of phosphatidylcholine-analogue-containing segmented polyurethanes, phosphatidylcholineanalogue-grafted polyurethanes, 2-methacryloyloxyethylphosphorylcholine-containing polymers, 2-methacryloyloxyethylphosphorylcholine-modi ed acrylamide hydrogel, etc. Design and synthesis of phosphatidylcholine-analogue-containing diols and their polyurethanes with various commercially available diisocyanates and phosphatidylcholine-analogue surface-modi ed polyurethanes are described. New ring-opening reagents such as 2-dimethylaminoethanol for the main-chain type of phosphatidylcholine-analogue-containing polyurethanes, N -methyldiethanolamine for the sidechain type of phosphatidylcholine-analogue-containing polyurethanesand trimethylamine for grafting phosphatidylcholine-analogue-containing vinyl monomers are discussed. A general reaction route to design and synthesize phosphatidylcholine-analogue-containing diols and polyurethanes is summarized. Various phosphatidylcholine-analogue-containing segmented polyurethanes are also discussed. Various phosphatidylcholine-analogue-containing diols, together with 1,4-butanediol or ethylenediamine as chain extender were used to synthesize phosphatidylcholine-analogue-containing segmented polyurethanes or polyurethaneureas, which are based on diphenylmethane diisocyanate and various types of soft segments such as a polycarbonate,polyether, polyester and hydrocarbon diols. Character-310 T. Nakaya and Y. Li ization techniques for phosphatidylcholine-analogue-containing polyurethanes and polymers are also described. These include infra-red spectroscopy, 1 H-NMR, viscosity and gel-permeation chromatography measurements for bulk property; X-ray diffraction methods for structure; dynamic viscoelasticity and tensile measurements for mechanical properties. Moreover, attenuated total re ectanceFourier transform infrared spectroscopy,electron spectroscopy for chemical analysis and contact angle measurements for surface properties are all described. Hemocompatibility ...

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“…The resulting polymers, Poly(4a). Poly (6). and Poly (7) were purified by reprecipitation from methanol solution with acetone.…”

Section: -(Acryloyloxy)ethyl-2-trimethylammonium)ethyl Phosphate (4a)mentioning

confidence: 99%

Preparation and Polymerization of 2-(Acryloyloxy)Ethyl-2-(Trimethylammonium)Ethyl Phosphate and 4-(Acryloyloxy)Butyl-2-(Trimethylammonium)Ethyl Phosphate

Seo

Nakaya

1995

Journal of Macromolecular Science, Part A

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2-(Acryloyloxyl)ethyl-2-(trimethylammonium)ethyl phosphate (4a)and 4 (acryloyloxyl)butyl-2-( trimethylammonium)ethyl phosphate (4b) were prepared and characterized by their IR and lH NMR spestral data and elemental analyses. 4a was homopolymerized and compolymerized with 2-hydroxyethyl acrylate, stearyl acrylate, and l~-dioleylacyIglyce~loI-2-acrylate using 2,2'-azoisobutyronitrile (AIBN) as initiator. Poly (4a) of the resultant polymers exhibited liquid crystalline behaviors from 118 up to 152 O C observed by a polarization microscopy. Moreover, the water-soluble polymer, Poly ( k ) , among the resulting polymers showed a polyelectrolyte behavior from its viscosity measurement.

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Polymeric phospholipid analogues, 14. The convenient preparation of a vinyl monomer containing a phospholipid analogue

Cited by 67 publications

References 8 publications

Phospholipid Polymers

Phospholipid Polymers

Recent progress of phospholipid polymers

Preparation and Polymerization of 2-(Acryloyloxy)Ethyl-2-(Trimethylammonium)Ethyl Phosphate and 4-(Acryloyloxy)Butyl-2-(Trimethylammonium)Ethyl Phosphate

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