PMID- 32264043
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20200408
IS  - 2050-7518 (Electronic)
IS  - 2050-750X (Linking)
VI  - 5
IP  - 14
DP  - 2017 Apr 14
TI  - Supramolecular amphiphiles based on cyclodextrin and hydrophobic drugs.
PG  - 2644-2654
LID - 10.1039/c6tb03272a [doi]
AB  - Herein we report a novel "supra-prodrug-type" superamphiphile design: via a 
      redox-sensitive self-immolative linker, a hydrophobic drug molecule was labeled 
      with an azobenzene moiety, which was designed to be capped by a hydrophilic 
      cyclodextrin (CD) molecule. Four clinical hydrophobic drugs, 
      7-ethyl-10-hydroxycamptothecin (SN-38), doxorubicin (DOX), phenytoin and 
      aliskiren, were investigated to directly participate in building a novel class of 
      superamphiphile, in which the CD moiety plays as the hydrophilic head and the 
      drug as the hydrophobic tail. This novel type of superamphiphile can further 
      self-assemble into vesicular or tubular structures, characterized by transmission 
      electron microscope (TEM), scanning electron microscope (SEM) and dynamic light 
      scattering (DLS). The possible self-assembly mechanism is given based on multiple 
      pieces of evidence, including nuclear magnetic resonance (NMR), Fourier transform 
      infrared spectroscopy (FT-IR), X-ray diffraction (XRD) and Ultraviolet-visible 
      spectroscopy (UV-vis) results. The reconversion kinetics of the prodrug as a 
      function of glutathione (GSH) in the presence or absence of UV irradiation is 
      presented. Cell experiments indicate that the "supra-prodrug" can be facially 
      endowed with a function by a simple substitution with another functionalized 
      host. We hope this work can provide new reference in the field of drug screening, 
      formulation and delivery.
FAU - Sun, Tao
AU  - Sun T
AD  - Key Laboratory of Smart Drug Delivery (Ministry of Education), State Key 
      Laboratory of Medical Neurobiology, Department of Pharmaceutics, School of 
      Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai 201203, P. R. China. 
      jiangchen@shmu.edu.cn.
FAU - Wang, Qingbing
AU  - Wang Q
FAU - Bi, Yunke
AU  - Bi Y
FAU - Chen, Xinli
AU  - Chen X
FAU - Liu, Lisha
AU  - Liu L
FAU - Ruan, Chunhui
AU  - Ruan C
FAU - Zhao, Zhifeng
AU  - Zhao Z
FAU - Jiang, Chen
AU  - Jiang C
LA  - eng
PT  - Journal Article
DEP - 20170320
PL  - England
TA  - J Mater Chem B
JT  - Journal of materials chemistry. B
JID - 101598493
SB  - IM
EDAT- 2017/04/14 00:00
MHDA- 2017/04/14 00:01
CRDT- 2020/04/09 06:00
PHST- 2020/04/09 06:00 [entrez]
PHST- 2017/04/14 00:00 [pubmed]
PHST- 2017/04/14 00:01 [medline]
AID - 10.1039/c6tb03272a [doi]
PST - ppublish
SO  - J Mater Chem B. 2017 Apr 14;5(14):2644-2654. doi: 10.1039/c6tb03272a. Epub 2017 
      Mar 20.