Maleimide-functionalized closo-dodecaborate albumin conjugates (MID-AC): Unique ligation at cysteine and lysine residues enables efficient boron delivery to tumor for neutron capture therapy

被引:54
作者
Kikuchi, Shunsuke [1 ]
Kanoh, Daisuke [2 ]
Sato, Shinichi [1 ]
Sakurai, Yoshinori [3 ]
Suzuki, Minoru [4 ]
Nakamura, Hiroyuki [1 ]
机构
[1] Tokyo Inst Technol, Inst Innovat Res, Lab Chem & Life Sci, Yokohama, Kanagawa, Japan
[2] Gakushuin Univ, Fac Sci, Dept Chem, Tokyo, Japan
[3] Kyoto Univ, Inst Res Reactor, Dept Radiat Life Sci & Radiat Med Sci, Osaka, Japan
[4] Kyoto Univ, Inst Res Reactor, Particle Radiat Oncol Res Ctr, Osaka, Japan
关键词
Boron neutron capture therapy (BNCT); Closo-dodecaborate; Albumin modification; Maleimide; Boron delivery system; HUMAN SERUM-ALBUMIN; RECURRENT HEAD; MACROMOLECULAR THERAPEUTICS; METHOTREXATE-ALBUMIN; CANCER; LIPOSOMES; NANOPARTICLES; VEHICLES; TRIAL; ANION;
D O I
10.1016/j.jconrel.2016.07.017
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Maleimide-conjugating closo-dodecaborate sodium form 5c (MID) synthesized by the nucleophilic ring-opening reaction of closo-dodecaborate-1,4-dioxane complex 2 with tetrabutylammonium (TBA) azide was found to conjugate to free SH of cysteine and lysine residues in BSA under physiological conditions, forming highly boronated BSA that showed high and selective accumulation in tumor and significant tumor growth inhibition in colon 26 tumor-bearing mice subjected to thermal neutron irradiation. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:160 / 167
页数:8
相关论文
共 40 条
[11]   Protein nanoparticles as drug carriers in clinical medicine [J].
Hawkins, Michael J. ;
Soon-Shiong, Patrick ;
Desai, Neil .
ADVANCED DRUG DELIVERY REVIEWS, 2008, 60 (08) :876-885
[12]   Effectiveness of BNCT for recurrent head and neck malignancies [J].
Kato, I ;
Ono, K ;
Sakurai, Y ;
Ohmae, M ;
Maruhashi, A ;
Imahori, Y ;
Kirihata, M ;
Nakazawa, M ;
Yura, Y .
APPLIED RADIATION AND ISOTOPES, 2004, 61 (05) :1069-1073
[13]   Development of High Boron Content Liposomes and Their Promising Antitumor Effect for Neutron Capture Therapy of Cancers [J].
Koganei, Hayato ;
Ueno, Manabu ;
Tachikawa, Shoji ;
Tasaki, Lisa ;
Ban, Hyun Seung ;
Suzuki, Minoru ;
Shiraishi, Kouichi ;
Kawano, Kumi ;
Yokoyama, Masayuki ;
Maitani, Yoshie ;
Ono, Koji ;
Nakamura, Hiroyuki .
BIOCONJUGATE CHEMISTRY, 2013, 24 (01) :124-132
[14]   A novel macromolecular prodrug concept exploiting endogenous serum albumin as a drug carrier for cancer chemotherapy [J].
Kratz, F ;
Müller-Driver, R ;
Hofmann, I ;
Drevs, J ;
Unger, C .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (07) :1253-1256
[15]   Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review [J].
Maeda, H ;
Wu, J ;
Sawa, T ;
Matsumura, Y ;
Hori, K .
JOURNAL OF CONTROLLED RELEASE, 2000, 65 (1-2) :271-284
[16]  
MATSUMURA Y, 1986, CANCER RES, V46, P6387
[17]  
MISHIMA Y, 1989, LANCET, V2, P388
[18]   Critical review, with an optimistic outlook, on Boron Neutron Capture Therapy (BNCT) [J].
Moss, Raymond L. .
APPLIED RADIATION AND ISOTOPES, 2014, 88 :2-11
[19]  
Ono K, 2016, J RAD RES
[20]   Synthesis of novel derivatives of closo-dodecaborate anion with azido group at the terminal position of the spacer [J].
Orlova, Anna V. ;
Kondakov, Nikolay N. ;
Kimel, Boris G. ;
Kononov, Leonid O. ;
Kononova, Elena G. ;
Sivaev, Igor B. ;
Bregadze, Vladimir I. .
APPLIED ORGANOMETALLIC CHEMISTRY, 2007, 21 (02) :98-100