Construction and transmembrane dissociation behavior of supramolecular assembly of quinolinocyclodextrin with porphyrin

Miao Yu; Yong Chen; Ning Zhang; Yu Liu

doi:10.1039/C0OB00080A

Construction and transmembrane dissociation behavior of supramolecular assembly of quinolinocyclodextrin with porphyrin

Miao Yu,^a Yong Chen,^a Ning Zhang^a and Yu Liu*^a

* Corresponding authors

^a Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, P. R. China
E-mail: yuliu@nankai.edu.cn
Fax: +86-022-23503625
Tel: +86-022-23503625

Abstract

Through the stoichiometric 2 : 1 coordination of Zn²⁺ with 4-amino-N-(2-methylquinolin-8-yl)benzenesulfonamide-modified per-methyl-β-cyclodextrin (MQAS-PMCD) and the strong inclusion complexation of permethyl-β-cyclodextrin cavity with meso-tetrakis-(4-sulfonatophenyl)-porphyrin (TSPP), an environment-sensitive Zn²⁺/cyclodextrin/porphyrin triad supramolecular assembly was constructed, and its structure was fully characterized by UV/vis spectroscopy, fluorescence spectroscopy, powder X-ray diffraction (XRD), scanning tunneling microscopy (STM) and transmission electron microscopy (TEM). Fluorescence spectrometric studies showed that this supramolecular assembly was stable and barely emitted green fluorescence in water due to the energy transfer process, but gave the strong green fluorescence when changing to a hydrophobic environment due to the disruption of the assembly. Further studies on the cell staining experiments by means of fluorescence microscopy showed that this supramolecular assembly was disrupted to release the MQAS-PMCD/Zn²⁺ and porphyrin components when interacting with the cell membrane. Subsequently, the released MQAS-PMCD/Zn²⁺ complex remained in the cell membrane, while the porphyrin component entered the cells. This transmembrane dissociation property of the supramolecular assembly will enable its application in the delivery of biological and drug molecules containing the anionic porphyrin skeleton such as β-octaphenyl-meso-tetra(4-carboxyl)-phenylporphyrin and so on.

Supplementary files

Publication details

The article was received on 05 May 2010, accepted on 22 Jun 2010 and first published on 26 Jul 2010

Article type: Paper

DOI: 10.1039/C0OB00080A

Citation: Org. Biomol. Chem., 2010,8, 4148-4154

Request permissions
Construction and transmembrane dissociation behavior of supramolecular assembly of quinolinocyclodextrin with porphyrin

M. Yu, Y. Chen, N. Zhang and Y. Liu, Org. Biomol. Chem., 2010, 8, 4148
DOI: 10.1039/C0OB00080A
If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using RightsLink. Go to our Instructions for using RightsLink page for details.

Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.

For reproduction of material from PCCP:
Reproduced from Ref. XX with permission from the PCCP Owner Societies.

For reproduction of material from PPS:
Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.

For reproduction of material from all other RSC journals and books:
Reproduced from Ref. XX with permission from The Royal Society of Chemistry.
If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

In all cases the Ref. XX is the XXth reference in the list of references.

If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC

For reproduction of material from PCCP:
[Original citation] - Reproduced by permission of the PCCP Owner Societies

For reproduction of material from PPS:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC

For reproduction of material from all other RSC journals:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry
If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Organic & Biomolecular Chemistry

Construction and transmembrane dissociation behavior of supramolecular assembly of quinolinocyclodextrin with porphyrin

Abstract

Supplementary files

Publication details

Construction and transmembrane dissociation behavior of supramolecular assembly of quinolinocyclodextrin with porphyrin

Search articles by author

Spotlight

Advertisements