Synthesis, and characterization folate-conjugated photocleavable poly(4-substituted-ε-caprolactone) polymers for drug delivery

Abstract

Photo-cleavable polymers containing 5-hydroxy-2-nitrobenzyl alcohol (ONB) junction point between the target molecule of folic acid (FA) and the hydrophobic poly(4-substituted-ɛ-caprolactone) (PXCL_n) chain were synthesized. FA –terminated ONB-PXCL_n polymers formed micelles with critical micelle concentration (CMC) 1.2 – 64.3 mg L⁻¹. Fluorescence emission spectroscopy indicated the release of Nile red encapsulated FA-ONB-PXCL_n micelles in response to irradiation. Light-triggered bursts released were observed for drug-loaded FA-ONB-PXCL_n micelles. The nanoparticles exhibited nonsignificant toxicity at concentrations up to 300 µg mL⁻¹. Flow cytometry revealed that the uptake of folate-targeted doxorubicin (DOX) -encapsulated micelles by HeLa cells was faster than that of free DOX.

Graphical Abstract

Keywords:

• Photo-cleavable
• folic acid
• micellization
• polyester
• target

Additional information

Funding

The research was supported by grants from Ministry of Science and Technology [MOST 103-2221-E-182-071] and Chang Gung Memorial Hospital [CMRPD5D0012].