Synthesis and characterization of a hydrazone based pH-sensitive lipid polymer conjugate

Document Type


Conference Title/Conference Publication

242nd National Meeting and Exposition of American Chemical Society (ACS)


American Chemical Society (ACS)


Denver, CO

Conference Dates

August 28-September 1, 2011

Date of Presentation



A three-step synthesis of a lipid-polymer conjugate is presented. The lipid, 1,2-di-O-hexadecyl-rac-glycerol (DHG) is conjugated to polyethylene glycol 2000 (PEG2000) via a pH-sensitive hydrazone linker. The steps involved in the synthesis of the conjugate include 1) incorporation of an ester group on the DHG moiety 2) hydrozinolysis of the ester group to yield a DHG hydrazide 3) condensation of the DHG hydrazide with m-PEG2000 aldehyde to yield the DHG-Hydrazone-PEG2000 conjugate. This hydrazone-based conjugate shows a pH-dependent hydrolysis and can be incorporated into liposomes to trigger cargo release at low pH environments as in cancer tissues.

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