A silyl porphyrin derivative conjugated with 6-deoxy-6-sulfo-α-D-glucopyranose functions as an efficient photosensitizer for photodynamic therapy

被引:0
|
作者
Horiuchi, Hiroaki [1 ]
Nishikawa, Kota [1 ]
Ishii, Nozomi [1 ]
Kano, Koki [1 ]
Shinada, Shunsuke [2 ]
Osawa, Nene [1 ]
Horikoshi, Aoi [1 ]
Yoshihara, Toshitada [1 ]
Sugawara, Fumio [3 ]
Sakaguchi, Kengo [3 ]
Okustu, Tetsuo [1 ]
Katsura, Shinji [2 ,4 ]
Matsuo, Ichiro [1 ]
Oshige, Masahiko [2 ,4 ]
机构
[1] Gunma Univ, Grad Sch Sci & Technol, Div Mol Sci, Kiryu, Gunma 3768515, Japan
[2] Gunma Univ, Grad Sch Sci & Technol, Dept Environm Engn Sci, Kiryu, Gunma 3768515, Japan
[3] Tokyo Univ Sci, Fac Sci & Technol, Dept Appl Biol Sci, Noda, Chiba 2788510, Japan
[4] Gunma Univ Ctr Food Sci & Wellness GUCFW, Maebashi, Gunma 3718510, Japan
基金
日本学术振兴会;
关键词
Silyl porphyrin; Photodynamic therapy; Photosensitizer; 6-deoxy-6-sulfo-alpha-D-glucopyranose; PHOTOPHYSICAL PROPERTIES; TETRAPHENYLPORPHYRIN; OXYGEN; ENHANCEMENT; IMPROVES;
D O I
10.1016/j.pdpdt.2023.103898
中图分类号
R73 [肿瘤学];
学科分类号
100214 ;
摘要
We synthesized a new silyl porphyrin derivative conjugated with 6-deoxy-6-sulfo-alpha-d-glucopyranose (SGlc). Conjugation with SGlc improved A549 cellular uptake without significant changes in the photophysical and photochemical properties and subcellular localization. This improved cellular uptake led to enhanced photodynamic activity. Furthermore, conjugation with SGlc suppressed dark toxicity. These advantages were not observed for a conjugate with a glucose molecule. These results indicated that the conjugation with SGlc is a promising strategy for enhancing photodynamic efficacy.
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页数:7
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共 25 条
  • [1] D-GLUCOPYRANOSE 6-DEOXY-6-PHOSPHONIC ACID
    SMITHGRIFFIN, B
    BURGER, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (10) : 2336 - 2338
  • [2] Synthesis of 3-octadecanoxypropyl 6-deoxy-6-sulfo-α-D-glucopyranoside (ODSG) as a lipase-resistant SQAP derivative
    Oshige, Masahiko
    Kano, Koki
    Shinada, Shunsuke
    Kawaguchi, Akifumi
    Uchida, Takato
    Ishii, Nozomi
    Horiuchi, Hiroaki
    Sugawara, Fumio
    Sakaguchi, Kengo
    Matsuo, Ichiro
    Katsura, Shinji
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2021, 52
  • [3] SYNTHESES OF 4-O-ALPHA-D-GALACTOPYRANOSYL-D-GLUCOPYRANOSE AND 4-O-(6-DEOXY-ALPHA-D-GALACTOPYRANOSYL)-D-GLUCOPYRANOSE BY CHEMICAL MODIFICATIONS OF MALTOSE
    MORI, M
    HAGA, M
    TEJIMA, S
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1975, 23 (07) : 1480 - 1487
  • [4] Testing of efficacy of photodynamic therapy with a new photosensitizer - a of chlorin e6 derivative (BLC 1010)
    Stranadko, EP
    Riabov, MV
    Volkova, NN
    Spaniol, S
    Rauschning, W
    Nifantiev, NE
    [J]. LASER-TISSUE INTERACTIONS, THERAPEUTIC APPLICATIONS, AND PHOTODYNAMIC THERAPY, 2001, 4433 : 155 - 157
  • [5] 1,6-epithio- and 1,6-episeleno-β-D-glucopyranose:: Useful adjuncts in the synthesis of 6-deoxy-β-D-glucopyranosides
    Stick, RV
    Tilbrook, DMG
    Williams, SJ
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (07) : 685 - 693
  • [6] Synthesis and ring-opening reaction of 1,6-anhydro-6-deoxy-6-thio-2,3, 4-tri-O-benzyl-β-D-glucopyranose
    Hatanaka, K
    Shirasaka, M
    Katayose, M
    Watanabe, N
    Yuasa, H
    Hashimoto, H
    [J]. POLYMER JOURNAL, 2000, 32 (03) : 297 - 299
  • [7] Synthesis and Ring-Opening Reaction of 1,6-Anhydro-6-deoxy-6-thio-2, 3, 4-tri-O-benzyl-β-D-glucopyranose
    Kenichi Hatanaka
    Motonori Shirasaka
    Masayuki Katayose
    Naoko Watanabe
    Hideya Yuasa
    Hironobu Hashimoto
    [J]. Polymer Journal, 2000, 32 : 297 - 299
  • [8] Heparinase 1 selectivity for the 3,6-di-O-sulfo-2-deoxy-2-sulfamido-α-D-glucopyranose (1,4) 2-O-sulfo-α-L-idopyranosyluronic acid (GlcNS3S6S-IdoA2S) linkages
    Xiao, Zhongping
    Zhao, Wenjing
    Yang, Bo
    Zhang, Zhenqing
    Guan, Huashi
    Linhardt, Robert J.
    [J]. GLYCOBIOLOGY, 2011, 21 (01) : 13 - 22
  • [9] RADIOSYNTHESIS OF 1, 3, 4, 6-TETRA-O-ACETYL-2-DEOXY-2-([18F] FLUOROACETAMIDO)-D-GLUCOPYRANOSE FOR IMAGING OF BACTERIAL INFECTIONS
    Pozo, M. E. Martinez
    Ido, T.
    Kiyono, Y.
    Noriki, S.
    Inai, K.
    Mandap, K.
    Kobayashi, M.
    Fujibayashi, Y.
    [J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2009, 52 : S167 - S167
  • [10] Orally efficacious novel small molecule 6-chloro-6-deoxy-1,2,3,4-tetra-O-galloyl-α-D-glucopyranose selectively and potently stimulates insulin receptor and alleviates diabetes
    Cao, Yanyan
    Li, Yunsheng
    Kim, Jaekyung
    Ren, Yulin
    Himmeldirk, Klaus
    Liu, Yi
    Qian, Yanrong
    Liu, Fengming
    Chen, Xiaozhuo
    [J]. JOURNAL OF MOLECULAR ENDOCRINOLOGY, 2013, 51 (01) : 15 - 26