Self-Assembly Behavior of Emissive Urea Benzene Derivatives Enables Heat-Induced Accumulation in Tumor Tissue

被引:22
作者
Araki, Takeru [1 ]
Murayama, Shuhei [2 ]
Usui, Kazuteru [1 ]
Shimada, Takashi [1 ]
Aoki, Ichio [2 ]
Karasawa, Satoru [1 ,3 ]
机构
[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Higashi Ku, 3-1-1 Maidashi, Fukuoka 8128582, Japan
[2] Natl Inst Radiol Sci, Dept Mol Imaging & Theranost, QST, Inage Ku, Anagawa 4-9-1, Chiba 2638555, Japan
[3] Japan Sci & Technol Agcy, PRESTO, Kawaguchi, Saitama 3320012, Japan
关键词
Self-assembly; nanoparticles; LCST; tumor imaging; fluorescence; CRYSTAL TRANSFORMATION; NANOPARTICLES; FLUORESCENCE; MOLECULES; WATER; PH;
D O I
10.1021/acs.nanolett.6b05371
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this study we describe the construction of a system composed of thermally responsive molecules that can be induced to accumulate in tumor tissues by heating. EgX molecules consisting of an urea benzene framework and oligoethylene glycol (OEG) functional groups with an emissive aminoquinoline formed nanoparticles (NPs) similar to 10 nm in size at 23 degrees C with a fluorescence quantum yield of 7-10%. At higher temperatures, additional self-assembly occurred as a result of OEG dehydration, and the NPs grew to over 1000 nm in size; this was accompanied by low critical solution temperature behavior. EgXs accumulated in tumor tissues of mice at a body temperature of around 33-35 degrees C, an effect that was accelerated by external heating around the tumor to approximately 40 degrees C as a result of increased particle size and enhanced retention in tissue. These EgX NPs can serve as a tool for in vivo monitoring of tumor progression and response to treatment.
引用
收藏
页码:2397 / 2403
页数:7
相关论文
共 22 条
[1]   Crystal Structures and Emitting Properties of Trifluoromethylaminoquinoline Derivatives: Thermal Single-Crystal-to-Single-Crystal Transformation of Polymorphic Crystals That Emit Different Colors [J].
Abe, Yuichiro ;
Karasawa, Satoru ;
Koga, Noboru .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (47) :15038-15048
[2]   Selective calcium ion sensing with a bichromophoric squaraine foldamer [J].
Arunkumar, E ;
Ajayaghosh, A ;
Daub, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) :3156-3164
[3]   Tuning Thermoresponsive Supramolecular G-Quadruplexes [J].
Betancourt, Jose E. ;
Rivera, Jose M. .
LANGMUIR, 2015, 31 (07) :2095-2103
[4]   The EPR effect: Unique features of tumor blood vessels for drug delivery, factors involved, and limitations and augmentation of the effect [J].
Fang, Jun ;
Nakamura, Hideaki ;
Maeda, Hiroshi .
ADVANCED DRUG DELIVERY REVIEWS, 2011, 63 (03) :136-151
[5]   Thermo-responsive Diblock Copolymer Worm Gels in Non-polar Solvents [J].
Fielding, Lee A. ;
Lane, Jacob A. ;
Derry, Matthew J. ;
Mykhaylyk, Oleksandr O. ;
Armes, Steven P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) :5790-5798
[6]   Synthesis and surface engineering of iron oxide nanoparticles for biomedical applications [J].
Gupta, AK ;
Gupta, M .
BIOMATERIALS, 2005, 26 (18) :3995-4021
[7]   Assemblies of Functional Small-Sized Molecules Having 4-Amino-2,2,6,6-tetramethylpiperidine-1-oxyl Responsive to Heat and pH in Water and Their Water Proton Relaxivities [J].
Hayashi, Hiroyuki ;
Ohkubo, Kengo ;
Karasawa, Satoru ;
Koga, Noboru .
LANGMUIR, 2011, 27 (20) :12709-12719
[8]   Photoinduced Macroscopic Morphological Transformation of an Amphiphilic Diarylethene Assembly: Reversible Dynamic Motion [J].
Higashiguchi, Kenji ;
Taira, Genki ;
Kitai, Jun-ichiro ;
Hirose, Takashi ;
Matsuda, Kenji .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) :2722-2729
[9]   Regioselective Photocyclizations of Di(quinolinyl)arylamines and Tri(quinolinyl)amine with Emission Color Changes and Photoreaction-Induced Self-Assemblies [J].
Karasawa, Satoru ;
Todo, Jun-ichi ;
Usui, Kazuteru ;
Harada, Naomi ;
Yoza, Kenji ;
Suemune, Hiroshi ;
Koga, Noboru .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (23) :7771-7781
[10]   Crystal Structures, Thermal Properties, and Emission Behaviors of N,N-R-Phenyl-7-amino-2,4-trifluoromethylquinoline Derivatives: Supercooled Liquid-to-Crystal Transformation Induced by Mechanical Stimuli [J].
Karasawa, Satoru ;
Hagihara, Ryusuke ;
Abe, Yuichiro ;
Harada, Naomi ;
Todo, Jun-ichi ;
Koga, Noboru .
CRYSTAL GROWTH & DESIGN, 2014, 14 (05) :2468-2478