Amphiphilic trismethylpyridylporphyrin-fullerene (C70) dyad: an efficient photosensitizer under hypoxia conditions

被引:31
作者
Guan, Mirong [1 ]
Qin, Tingxiao [2 ]
Ge, Jiechao [3 ]
Zhen, Mingming [1 ]
Xu, Wei [1 ]
Chen, Daiqin [1 ]
Li, Shumu [1 ]
Wang, Chunru [1 ]
Su, Hongmei [2 ]
Shu, Chunying [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Key Lab Mol Nanostruct & Nanotechnol, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[2] Chinese Acad Sci, Inst Chem, State Key Lab Mol React Dynam, BNLMS, Beijing 100190, Peoples R China
[3] Chinese Acad Sci, TIPC, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
SINGLET-OXYGEN GENERATION; PHOTODYNAMIC THERAPY; PHOTORADIATION THERAPY; ENERGY-TRANSFER; CANCER; PORPHYRIN; HEMATOPORPHYRIN; NANOPARTICLES; NANOPLATFORM; DELIVERY;
D O I
10.1039/c4tb01314j
中图分类号
TB3 [工程材料学]; R318.08 [生物材料学];
学科分类号
0805 ; 080501 ; 080502 ;
摘要
Amphiphilic trismethylpyridylporphyrin-C-70 (PC70) dyad with improved photosensitization has been successfully prepared. The PC70 dyad forms a liposomal nanostructure through molecular self-assembling. An increased absorption coefficient in the visible region, good biocompatibility, and high photostability were observed on the self-assembling structure. Surprisingly, in comparison with previously reported photosensitizer porphyrins, PC70 exhibited an enhanced photodynamic therapy (PDT) effect under hypoxia conditions. Further investigations illustrated that PC70 went through an extremely long-life triplet state (211.3 mu s) under hypoxia, which enabled the exiguous oxygen to approach and interact with the activated (P-3-C-70)* more efficiently and produce more singlet oxygen. This would overcome the problem of existing photosensitizers of low PDT efficiency in cancerous tissues under hypoxia. The excellent properties of PC70 dyad make it a promising phototherapeutic agent, especially for the treatment of early-and late-stage cancers under shallow and hypoxia tissues.
引用
收藏
页码:776 / 783
页数:8
相关论文
共 73 条
[1]   Photodynamic activity of a new sensitizer derived from porphyrin-C60 dyad and its biological consequences in a human carcinoma cell line [J].
Alvarez, M. Gabriela ;
Prucca, Cesar ;
Milanesio, M. Elisa ;
Durantini, Edgardo N. ;
Rivarola, Viviana .
INTERNATIONAL JOURNAL OF BIOCHEMISTRY & CELL BIOLOGY, 2006, 38 (12) :2092-2101
[2]   Peroxidase-Like Activity of Fe3O4@Carbon Nanoparticles Enhances Ascorbic Acid-Induced Oxidative Stress and Selective Damage to PC-3 Prostate Cancer Cells [J].
An, Qiao ;
Sun, Chuanyu ;
Li, Dian ;
Xu, Ke ;
Guo, Jia ;
Wang, Changchun .
ACS APPLIED MATERIALS & INTERFACES, 2013, 5 (24) :13248-13257
[3]   Nanomaterials: Applications in Cancer Imaging and Therapy [J].
Barreto, Jose A. ;
O'Malley, William ;
Kubeil, Manja ;
Graham, Bim ;
Stephan, Holger ;
Spiccia, Leone .
ADVANCED MATERIALS, 2011, 23 (12) :H18-H40
[4]   Novel Multifunctional Acyloxyalkyl Ester Prodrugs of 5-Aminolevulinic Acid Display Improved Anticancer Activity Independent and Dependent on Photoactivation [J].
Berkovitch, Gili ;
Doron, Dvir ;
Nudelman, Abraham ;
Malik, Zvi ;
Rephaeli, Ada .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (23) :7356-7369
[5]   First soluble M@C60 derivatives provide enhanced access to metallofullerenes and permit in vivo evaluation of Gd@C60[C(COOH)2]10 as a MRI contrast agent [J].
Bolskar, RD ;
Benedetto, AF ;
Husebo, LO ;
Price, RE ;
Jackson, EF ;
Wallace, S ;
Wilson, LJ ;
Alford, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) :5471-5478
[6]   Exploiting tumour hypoxia in cancer treatment [J].
Brown, JM ;
William, WR .
NATURE REVIEWS CANCER, 2004, 4 (06) :437-447
[7]   Designing Excited States: Theory-Guided Access to Efficient Photosensitizers for Photodynamic Action [J].
Cakmak, Yusuf ;
Kolemen, Safacan ;
Duman, Selin ;
Dede, Yavuz ;
Dolen, Yusuf ;
Kilic, Bilal ;
Kostereli, Ziya ;
Yildirim, Leyla Tatar ;
Dogan, A. Lale ;
Guc, Dicle ;
Akkaya, Engin U. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) :11937-11941
[8]   Imaging and Photodynamic Therapy: Mechanisms, Monitoring, and Optimization [J].
Celli, Jonathan P. ;
Spring, Bryan Q. ;
Rizvi, Imran ;
Evans, Conor L. ;
Samkoe, Kimberley S. ;
Verma, Sarika ;
Pogue, Brian W. ;
Hasan, Tayyaba .
CHEMICAL REVIEWS, 2010, 110 (05) :2795-2838
[9]   Pharmacokinetics and clinical effects of mono-L-aspartyl chlorin e6 (NPe6) photodynamic therapy in adult patients with primary or secondary cancer of the skin and mucosal surfaces [J].
Chan, AL ;
Juarez, M ;
Allen, R ;
Volz, W ;
Albertson, T .
PHOTODERMATOLOGY PHOTOIMMUNOLOGY & PHOTOMEDICINE, 2005, 21 (02) :72-78
[10]   Photodecomposition of retinyl palmitate in ethanol by UVA light-formation of photodecomposition products, reactive oxygen species, and lipid peroxides [J].
Cherng, SH ;
Xia, QS ;
Blankenship, LR ;
Freeman, JP ;
Wamer, WG ;
Howard, PC ;
Fu, PP .
CHEMICAL RESEARCH IN TOXICOLOGY, 2005, 18 (02) :129-138