4.6 Article

Supramolecular Nanoassemblies of an Amphiphilic Porphyrin-Cyclodextrin Conjugate and Their Morphological Transition from Vesicle to Network

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 11, 页码 4457-4464

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405943

关键词

cyclodextrins; nanostructures; porphyrinoids; self-assembly; supramolecular chemistry

资金

  1. 973 Program [2011CB932500]
  2. NNSFC [21372128, 91227107]

向作者/读者索取更多资源

An amphiphilic compound, 5-(4'-dodecyloxyphenyl)-10,15,20-tri(permethyl-beta-CD)-modified Zn-II-porphyrin (1; beta-CD=beta-cyclodextrin), was synthesized by means of the click reaction of an alkylated Zn-porphyrin derivative with 6-deoxy-6-azidopermethyl-beta-CD. The complexation between 1 and tetrasodium tetraphenylporphyrintetrasulfonate (5) with different molar ratios led to the formation of two distinctly different nanoarchitectures, which were proven to be vesicle and network aggregates, respectively, by using dynamic light scattering, scanning electron microscopy, transmission electron microscopy, and atomic force microscopy. On the basis of the results of the time-dependent TEM studies, fluorescence, and NMR spectroscopic measurements, we have determined that the mechanism of the morphology transition from vesicles to networks is controlled by the stepwise complexation of 1 with 5. Furthermore, these supramolecular nanoarchitectures show the controlled-release property of doxorubicin as potential candidates for drug delivery.

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