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Selective binding and controlled release of anticancer drugs by polyanionic cyclodextrins.

Abstract：

:The binding stoichiometry, binding constants, and inclusion mode of some water-soluble negatively charged cyclodextrin derivatives, i.e. heptakis-[6-deoxy-6-(3-sulfanylpropanoic acid)]-β-cyclodextrin(H1), heptakis-[6-deoxy-6-(2-sulfanylacetic acid)]-β-cyclodextrin(H2), mono-[6-deoxy-6-(3-sulfanylpropanoic acid)]-β-cyclodextrin (H3) and mono-[6-deoxy-6-(2-sulfanylacetic acid)]-β-cyclodextrin (H4), with three anticancer drugs, i.e. irinotecan hydrochloride; topotecan hydrochloride; doxorubicin hydrochloride, were investigated by means of 1H NMR, UV-Vis spectroscopy, mass spectra and 2D NMR. Polyanionic cyclodextrins H1-H2 showed the significantly high binding abilities of up to 2.6 × 104-2.0 × 105 M-1 towards the selected anticancer drugs, which were nearly 50-1000 times higher than the corresponding Ks values of native β-cyclodextrin. In addition, these polyanionic cyclodextrins also showed the pH-controlled release behaviors. That is, the anticancer drugs could be efficiently encapsulated in the cyclodextrin cavity at a pH value similar to that of serum but sufficiently released at an endosomal pH value of a cancer cell, which would make these cyclodextrin derivatives the potential carriers for anticancer drugs.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Cheng JG,Yu HJ,Chen Y,Liu Y

doi

10.1016/j.bmc.2018.03.013

subject

Has Abstract

pub_date

2018-05-15 00:00:00

pages

2287-2290

issue

9

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(18)30242-6

journal_volume

26

pub_type

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