Synthesis of poly(oxyethylene phosphonate)s bearing oxirane groups in the side chain

Abstract

The interaction between poly(oxyethylene phosphonate)s and 1,2‐epoxy‐7‐octene has been investigated. It has been established that in the presence of benzoyl peroxide there proceeds a selective addition of the P()H group to the C()C double bond. Poly(oxyethylene phosphonate)s bearing oxirane groups in the side chain have been synthesized. The new polymers can be used as polymer carriers of drugs. © 1997 John Wiley & Sons, Inc.

The Use of Transesterification Method for Obtaining Phosphorus‐Containing Polymers

“…The following four important methods for the polymeric phosphonate esters preparation have been used during past decades: – polycondensation, – polyaddition, – the ROP of cyclic phosphonate monomers, and – transesterification …”

“…A typical reaction of the P–H group is the addition reaction to unsaturated carbonyl group C=O (Abramov reaction), to C=C (Pudovik reaction), or to the more unsaturated C≡C, resulting into P–C bond formation . The addition of the P–H groups of poly(oxyethylene H‐phosphonate)s to 1,2‐epoxy‐7‐octene in the presence of the catalyst benzoylperoxide leads to a poly(oxyethylene phosphonate)s bearing oxirane cycle in the side chain . If in the same precursor polymers react with chloroacetone under phase‐transfer catalysis conditions, the addition reaction will produce polymers bearing hydroxyl and oxirane groups …”

Immobilization of Aminothiols on Poly(oxyalkylene phosphates). Formation of Poly(oxyethylene phosphates)/Cysteamine Complexes and Their Radioprotective Efficiency

“…Dimethyl phosphonate (Fluka AG) was purified by standard procedures. PEG with average molecular weight 200, 400, and 600 Da (Fluka AG) was dried prior to use at 120 °C by bubbling a stream of dry argon through the melt and simultaneous application of dynamic vacuum 7e. Cy hydrochloride was purchased from Fluka AG and used as supplied.…”

“…The major goals of the present study are the immobilization of the conventional chemical protective agent cysteamine (Cy) on POAP via ionic bonds and the evaluation of the radioprotective efficiency of the complexes formed. These experiments combine and extend our line of inquiry toward development of low-toxicity polymers for drug encapsulation and transport and capable of binding highly efficient radiomodifying agents 7g…”

Phosphorus-Containing Polymers: A Great Opportunity for the Biomedical Field

“…Poly(oxyethylene H -phosphonates) − were also used in biomedical field because of their biocompatibility, controlled biodegradability, and the presence of a highly reactive P–H bond in the building units of the polymer chain (Scheme ). These water-soluble polymers showed low toxicity and could be easily functionalized. − For example, immobilization of aminothiols on poly(oxyalkylene phosphates) was achieved: the incorporation of the cysteamine, a well-known clinically tested chemical radioprotector, into poly(oxyethylene phosphate) led to a significant reduction of its toxicity. The drug dose needed for efficient radio protection was also reduced .…”