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Preparation of chondroitin sulfate-adipic acid dihydrazide-doxorubicin conjugate and its antitumour characteristics against LLC cells.
Journal of Drug Targeting 2017 September
Macromolecule-antitumour drug conjugates can reach tumour sites specifically via the enhanced permeability and retention (EPR) effect. It is desirable to release the drug efficiently from the conjugate at acidic pH in the tumour tissue or in the endosomes of cancer cells. In this study, we attempted to produce a carrier system with a labile chemical bond at acidic pH. Adipic acid dihydrazide (ADH)-chondroitin sulfate (CS) (termed CS-ACH) was synthesised by a two-step method, with the introduction of formyl groups followed by reductive amination using ADH. Doxorubicin (DOX) was conjugated to CS-ACH by simple mixing at acidic pH. The conjugate, designated CS-ACH-DOX, showed gradual drug release pH dependently at 37 °C; after incubation for seven days, more than 60% of DOX was released at pH 4, whereas less than 20% was released at pH 7. CS-ACH-DOX showed in vitro cytotoxicity against Lewis lung carcinoma (LLC) cells, which was less effective than that of DOX itself. However, CS-ACH-DOX inhibited tumour growth more than DOX in LLC tumour-bearing mice. These results suggested that CS-ACH-DOX might accumulate in tumours via the EPR effect and release DOX effectively at acidic pH. CS-ACH-DOX was considered to act as a drug delivery system with tumour targeting.
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