Synthesis of Water-Soluble Aminoaryloxy-Methylamino Cosubstituted Polyphosphazenes as Carrier Species for Biologically Active Agents

Synthesis of Water-Soluble Aminoaryloxy-Methylamino Cosubstituted Polyphosphazenes as Carrier Species for Biologically Active Agents

The water-soluble poly(aminoaryloxy-methylamino phosphazene) has been synthesized and investigated as a polymeric carrier species for the covalent attachment of biologically active agents. The cyclic trimeric model systems were utilized for the synthesis of polymeric analogues containing bioactive side groups. The sodium salt of 4-acetamidophenol was first allowed to react with (NPCl2)3 or (NPCl2)n and was then treated with excess methylamine to yield derivatives of type [NP(NHCH3)x(OArNHCOCH3)y]3 or [NP(NHCH3)x(OArNHCOCH3)y]n. The 4-acetamido groups were then hydrolyzed to 4-aminophenoxy units with potassium tert-butoxide. Coupling reactions between amino group and N-acetylglycine was accomplished with the use of dicyclohexylcarbodiimide. Their properties and structural characterization are discussed.