Citation: Yang Liu, Nan Song, Li Chen, Zhi-Gang Xie. BODIPY@Ir(Ⅲ) Complexes Assembling Organic Nanoparticles for Enhanced Photodynamic Therapy[J]. Chinese Journal of Polymer Science, ;2018, 36(3): 417-424. doi: 10.1007/s10118-018-2096-9 shu

BODIPY@Ir(Ⅲ) Complexes Assembling Organic Nanoparticles for Enhanced Photodynamic Therapy

Yang Liu ^a ,
Nan Song ^a ,
Li Chen ^a,, ,
Zhi-Gang Xie ^b,,

a.
Department of Chemistry, Northeast Normal University, Changchun 130024, China
b.
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China

Corresponding author: Li Chen, chenl686@nenu.edu.cn Zhi-Gang Xie, xiez@ciac.ac.cn
Received Date: 27 September 2017
Accepted Date: 23 November 2017
Available Online: 27 December 2017

We present a new cyclometalated Ir(Ⅲ) complexes IrBDP, which could self-assemble into organic nanoparticles (IrBDP NPs). IrBDP NPs show enhanced photodynamic effect and can be engulfed by HeLa cells for cell imaging as well as photodynamic therapy (PDT) upon low energy irradiation.
- BODIPY,
- Photodynamic therapy,
- Iridium complex
1. [1]
  Li H., Wang P., Deng Y., Zeng M., Tang Y., Zhu W. H., Cheng Y.. Combination of active targeting, enzyme-triggered release and fluorescent dye into gold nanoclusters for endomicroscopy-guided photothermal/photodynamic therapy to pancreatic ductal adenocarcinoma[J]. Biomaterials, 2017,139:30-38. doi: 10.1016/j.biomaterials.2017.05.030
2. [2]
  Li X., Gao M., Xin K., Zhang L., Ding D., Kong D., Wang Z., Shi Y., Kiessling F., Lammers T., Cheng J., Zhao Y.. Singlet oxygen-responsive micelles for enhanced photodynamic therapy[J]. J. Control. Release, 2017,260:12-21. doi: 10.1016/j.jconrel.2017.05.025
3. [3]
  Linares I. A. P., de Oliveira K. T., Perussi J. R.. Chlorin derivatives sterically-prevented from self-aggregation with high antitumor activity for photodynamic therapy[J]. Dyes Pigm., 2017,145:518-527. doi: 10.1016/j.dyepig.2017.06.011
4. [4]
  Xiong H., Zhou D., Zheng X., Qi Y., Wang Y., Jing X., Huang Y.. Stable amphiphilic supramolecular self-assembly based on cyclodextrin and carborane for the efficient photodynamic therapy[J]. Chem. Commun., 2017,53:3422-3425. doi: 10.1039/C6CC10059G
5. [5]
  Du E., Hu X., Roy S., Wang P., Deasy K., Mochizuki T., Zhang Y.. Taurine-modified Ru(ii)-complex targets cancerous brain cells for photodynamic therapy[J]. Chem. Commun., 2017,53:6033-6036. doi: 10.1039/C7CC03337K
6. [6]
  Gu B., Wu W., Xu G., Feng G., Yin F., Chong P. H. J., Qu J., Yong K. T., Liu B.. Precise two-photon photodynamic therapy using an efficient photosensitizer with aggregationinduced emission characteristics[J]. Adv. Mater., 2017,29(28). doi: 10.1002/adma.201701076
7. [7]
  Huang L., Li Z., Zhao Y., Yang J., Yang Y., Pendharkar A. I., Zhang Y., Kelmar S., Chen L., Wu W., Zhao J., Han G.. Enhancing photodynamic therapy through resonance energy transfer constructed near-Infrared photosensitized nanoparticles[J]. Adv. Mater., 2017,29(28). doi: 10.1002/adma.201604789
8. [8]
  Yue C., Yang Y., Song J., Alfranca G., Zhang C., Zhang Q., Yin T., Pan F., de la Fuente J. M., Cui D.. Mitochondriatargeting near-infrared light-triggered thermosensitive liposomes for localized photothermal and photodynamic ablation of tumors combined with chemotherapy[J]. Nanoscale, 2017,9:11103-11118. doi: 10.1039/C7NR02193C
9. [9]
  Zheng Y., Lu H., Jiang Z., Guan Y., Zou J., Wang X., Cheng R., Gao H.. Low-power white light triggered AIE polymer nanoparticles with high ROS quantum yield for mitochondria-targeted and image-guided photodynamic therapy[J]. J. Mater. Chem. B, 2017,5:6277-6281.
10. [10]
  Li Y., Zheng X., Zhang X., Liu S., Pei Q., Zheng M., Xie Z.. Porphyrin-based carbon dots for photodynamic therapy of hepatoma[J]. Adv. Healthc. Mater., 2017,6(1). doi: 10.1002/adhm.201600924
11. [11]
  Liu W., Wang Y. M., Li Y. H., Cai S. J., Yin X. B., He X. W., Zhang Y. K.. Fluorescent imaging-guided chemotherapyand-photodynamic dual therapy with nanoscale porphyrin metal-organic framework[J]. Small, 2017,13(17). doi: 10.1002/smll.201603459
12. [12]
  Rui L., Xue Y., Wang Y., Gao Y., Zhang W.. A mitochondria-targeting supramolecular photosensitizer based on pillararene for photodynamic therapy[J]. Chem. Commun., 2017,53:3126-3129. doi: 10.1039/C7CC00950J
13. [13]
  Zhang W., Lin W., Zheng X., He S., Xie Z.. Comparing effects of redox sensitivity of organic nanoparticles to photodynamic activity[J]. Chem. Mater., 2017,29:1856-1863. doi: 10.1021/acs.chemmater.7b00207
14. [14]
  Zheng X., Wang L., Pei Q., He S., Liu S., Xie Z.. Metal-organic framework@porous organic polymer nanocomposite for photodynamic therapy[J]. Chem. Mater., 2017,29:2374-2381. doi: 10.1021/acs.chemmater.7b00228
15. [15]
  Isik M., Guliyev R., Kolemen S., Altay Y., Senturk B., Tekinay T., Akkaya E. U.. Designing an intracellular fluorescent probe for glutathione:two modulation sites for selective signal transduction[J]. Org. Lett., 2014,16:3260-3263. doi: 10.1021/ol501272z
16. [16]
  Isik M., Ozdemir T., Turan I. S., Kolemen S., Akkaya E. U.. Chromogenic and fluorogenic sensing of biological thiols in aqueous solutions using BODIPY-based reagents[J]. Org. Lett., 2013,15:216-219. doi: 10.1021/ol303306s
17. [17]
  Göl C., Malkoç M., Yeşilot S., Durmuş M.. Novel zinc(Ⅱ) phthalocyanine conjugates bearing different numbers of BODIPY and iodine groups as substituents on the periphery[J]. Dyes Pigm., 2014,111:81-90. doi: 10.1016/j.dyepig.2014.06.003
18. [18]
  Kim B., Sui B., Yue X., Tang S., Tichy M. G., Belfield K. D.. In vitro photodynamic studies of a BODIPY-based photosensitizer[J]. Eur. J. Org. Chem., 2017(1):25-28.
19. [19]
  Wang W., Wang L., Li Z., Xie Z.. BODIPY-containing nanoscale metal-organic frameworks for photodynamic therapy[J]. Chem. Commun., 2016,52:5402-5405. doi: 10.1039/C6CC01048B
20. [20]
  Guo Z., Zou Y., He H., Rao J., Ji S., Cui X., Ke H., Deng Y., Yang H., Chen C., Zhao Y., Chen H.. Bifunctional platinated nanoparticles for photoinduced tumor ablation[J]. Adv. Mater., 2016,46(28):10155-10164.
21. [21]
  Liu Y., Li Z., Chen L., Xie Z.. Near infrared BODIPY-platinum conjugates for imaging, photodynamic therapy and chemotherapy[J]. Dyes Pigm., 2017,141:5-12. doi: 10.1016/j.dyepig.2017.01.075
22. [22]
  Cakmak Y., Kolemen S., Duman S., Dede Y., Dolen Y., Kilic B., Kostereli Z., Yildirim L. T., Dogan A. L., Guc D., Akkaya E. U.. Designing excited states:theory-guided access to efficient photosensitizers for photodynamic action[J]. Angew. Chem., 2011,50:11937-11941. doi: 10.1002/anie.v50.50
23. [23]
  Epelde-Elezcano N., Palao E., Manzano H., PrietoCastaneda A., Agarrabeitia A. R., Tabero A., Villanueva A., de la Moya S., Lopez-Arbeloa I., Martinez-Martinez V., Ortiz M. J.. Rational design of advanced photosensitizers based on orthogonal BODIPY dimers to finely modulate singlet oxygen generation[J]. Chem. Eur. J., 2017,23:4837-4848. doi: 10.1002/chem.v23.20
24. [24]
  Ozdemir T., Bila J. L., Sozmen F., Yildirim L. T., Akkaya E. U.. Orthogonal Bodipy trimers as photosensitizers for photodynamic action[J]. Org. Lett., 2016,18:4821-4823. doi: 10.1021/acs.orglett.6b02418
25. [25]
  Wu W., Cui X., Zhao J.. Hetero BODIPY-dimers as heavy atom-free triplet photosensitizers showing a long-lived triplet excited state for triplet-triplet annihilation upconversion[J]. Chem. Commun., 2013,49:9009-9011. doi: 10.1039/c3cc45470c
26. [26]
  Zhang X. F., Yang X.. Photosensitizer that selectively generates singlet oxygen in nonpolar environments:photophysical mechanism and efficiency for a covalent BODIPY dimer[J]. J. Phys. Chem. B, 2013,117:9050-9055. doi: 10.1021/jp405102m
27. [27]
  Mari C., Huang H., Rubbiani R., Schulze M., Würthner F., Chao H., Gasser G.. Evaluation of perylene bisimide-based RuⅡand IrⅢ complexes as photosensitizers for photodynamic therapy[J]. Eur. J. Inorg. Chem., 2017,2017:1745-1752.
28. [28]
  Wang L., Yin H., Cui P., Hetu M., Wang C., Monro S., Schaller R. D., Cameron C. G., Liu B., Kilina S., McFarland S. A., Sun W.. Near-infrared-emitting heteroleptic cationic iridium complexes derived from 2, 3-diphenylbenzo[g]quinoxaline as in vitro theranostic photodynamic therapy agents[J]. Dalton Trans, 2017,46:8091-8103. doi: 10.1039/C7DT00913E
29. [29]
  Xiang H., Chen H., Tham H. P., Phua S. Z. F., Liu J. G., Zhao Y.. Cyclometalated iridium(Ⅲ)-complex-based micelles for glutathione-responsive targeted chemotherapy and photodynamic therapy[J]. ACS Appl. Mater. Interfaces, 2017,9:27553-27562. doi: 10.1021/acsami.7b09506
30. [30]
  Zheng Y., He L., Zhang D. Y., Tan C. P., Ji L. N., Mao Z. W.. Mixed-ligand iridium(Ⅲ) complexes as photodynamic anticancer agents[J]. Dalton Trans., 2017,46:11395-11407. doi: 10.1039/C7DT02273E
31. [31]
  Liu J., Jin C., Yuan B., Liu X., Chen Y., Ji L., Chao H.. Selectively lighting up two-photon photodynamic activity in mitochondria with AIE-active iridium(Ⅲ) complexes[J]. Chem. Commun., 2017,53:2052-2055. doi: 10.1039/C6CC10015E
32. [32]
  McKenzie L. K., Sazanovich I. V., Baggaley E., Bonneau M., Guerchais V., Williams J. A., Weinstein J. A., Bryant H. E.. Metal complexes for two-photon photodynamic therapy:a cyclometallated iridium complex induces two-photon photosensitization of cancer cells under near-IR light[J]. Chem. Eur. J., 2017,23:234-238. doi: 10.1002/chem.v23.2
33. [33]
  Nam J. S., Kang M. G., Kang J., Park S. Y., Lee S. J., Kim H. T., Seo J. K., Kwon O. H., Lim M. H., Rhee H. W., Kwon T. H.. Endoplasmic reticulum-localized iridium(Ⅲ) complexes as efficient photodynamic therapy agents via protein modifications[J]. J. Am. Chem. Soc., 2016,138:10968-10977. doi: 10.1021/jacs.6b05302
34. [34]
  Qiu K., Ouyang M., Liu Y., Huang H., Liu C., Chen Y., Ji L., Chao H.. Two-photon photodynamic ablation of tumor cells by mitochondria-targeted iridium(Ⅲ) complexes in aggregate states[J]. J. Mater. Chem. B, 2017,5:5488-5498. doi: 10.1039/C7TB00731K
35. [35]
  Tian X., Zhu Y., Zhang M., Luo L., Wu J., Zhou H., Guan L., Battaglia G., Tian Y.. Localization matters:a nuclear targeting two-photon absorption iridium complex in photodynamic therapy[J]. Chem. Commun., 2017,53:3303-3306. doi: 10.1039/C6CC09470H
36. [36]
  Deligonul N., Browne A. R., Golen J. A., Rheingold A. L., Gray T. G.. Cyclometalated iridium(Ⅲ) complexes of azadipyrromethene chromophores[J]. Organometallics, 2014,33:637-643. doi: 10.1021/om4007032
37. [37]
  Zhou J., Gai L., Zhou Z., Mack J., Xu K., Zhao J., Qiu H., Chan K. S., Shen Z.. Highly efficient near IR photosensitizers based on Ir-C bonded porphyrin-aza-BODIPY conjugates[J]. RSC Adv., 2016,6:72115-72120. doi: 10.1039/C6RA10131C
38. [38]
  Majumdar P., Yuan X., Li S., Le Guennic B., Ma J., Zhang C., Jacquemin D., Zhao J.. Cyclometalated Ir(Ⅲ) complexes with styryl-BODIPY ligands showing near IR absorption/emission:preparation, study of photophysical properties and application as photodynamic/luminescence imaging materials[J]. J. Mater. Chem. B, 2014,2:2838-2854. doi: 10.1039/C4TB00284A
39. [39]
  Palao E., Sola-Llano R., Tabero A., Manzano H., Agarrabeitia A. R., Villanueva A., Lopez-Arbeloa I., Martinez-Martinez V., Ortiz M. J.. Acetylacetonate BODIPY-biscyclometalated iridium(Ⅲ) complexes:effective strategy towards smarter fluorescent photosensitizer agents[J]. Chem. Eur. J., 2017,23:10139-10147. doi: 10.1002/chem.v23.42
40. [40]
  Sun J., Zhong F., Yi X., Zhao J.. Efficient enhancement of the visible-light absorption of cyclometalated Ir(Ⅲ) complexes triplet photosensitizers with BODIPY and applications in photooxidation and triplet-triplet annihilation upconversion[J]. Inorg. Chem., 2013,52:6299-6310. doi: 10.1021/ic302210b
41. [41]
  Tabrizi L., Chiniforoshan H.. New cyclometalated Ir(Ⅲ) complexes with NCN pincer and meso-phenylcyanamide BODIPY ligands as efficient photodynamic therapy agents[J]. RSC Adv., 2017,7:34160-34169. doi: 10.1039/C7RA05579J
42. [42]
  Khairoutdinov R. F., Doubova L. V., Haddon R. C., Saraf L.. Persistent photoconductivity in chemically modified single-wall carbon nanotubes[J]. J. Phys. Chem. B, 2004,108:19976-19981. doi: 10.1021/jp046495m
43. [43]
  Li Z., Zheng M., Guan X., Xie Z., Huang Y., Jing X.. Unadulterated BODIPY-dimer nanoparticles with high stability and good biocompatibility for cellular imaging[J]. Nanoscale, 2014,6:5662-5665. doi: 10.1039/C4NR00521J
44. [44]
  Liu Y., Song N., Chen L., Xie Z.. Triple-BODIPY organic nanoparticles with particular fluorescence emission[J]. Dyes Pigm., 2017,147:241-245. doi: 10.1016/j.dyepig.2017.08.026
1. [1]
  Qihang Wu , Hui Wen , Wenhai Lin , Tingting Sun , Zhigang Xie . Alkyl chain engineering of boron dipyrromethenes for efficient photodynamic antibacterial treatment. Chinese Chemical Letters, 2024, 35(12): 109692-. doi: 10.1016/j.cclet.2024.109692
2. [2]
  Leichen Wang , Anqing Mei , Na Li , Xiaohong Ruan , Xu Sun , Yu Cai , Jinjun Shao , Xiaochen Dong . Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy. Chinese Chemical Letters, 2024, 35(6): 108974-. doi: 10.1016/j.cclet.2023.108974
3. [3]
  Fuzheng Zhang , Chao Shi , Jiale Li , Fulin Jia , Xinyu Liu , Feiyang Li , Xinyu Bai , Qiuxia Li , Aihua Yuan , Guohua Xie . B-embedded narrowband pure near-infrared (NIR) phosphorescent iridium(Ⅲ) complexes and solution-processed OLED application. Chinese Chemical Letters, 2025, 36(1): 109596-. doi: 10.1016/j.cclet.2024.109596
4. [4]
  Beitong Zhu , Xiaorui Yang , Lirong Jiang , Tianhong Chen , Shuangfei Wang , Lintao Zeng . A portable and versatile fluorescent platform for high-throughput screening of toxic phosgene, diethyl chlorophosphate and volatile acyl chlorides. Chinese Chemical Letters, 2025, 36(1): 110222-. doi: 10.1016/j.cclet.2024.110222
5. [5]
  Wei Su , Xiaoyan Luo , Peiyuan Li , Ying Zhang , Chenxiang Lin , Kang Wang , Jianzhuang Jiang . Phthalocyanine self-assembled nanoparticles for type Ⅰ photodynamic antibacterial therapy. Chinese Chemical Letters, 2024, 35(12): 109522-. doi: 10.1016/j.cclet.2024.109522
6. [6]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
7. [7]
  Yu Qin , Mingyang Huang , Chenlu Huang , Hannah L. Perry , Linhua Zhang , Dunwan Zhu . O₂-generating multifunctional polymeric micelles for highly efficient and selective photodynamic-photothermal therapy in melanoma. Chinese Chemical Letters, 2024, 35(7): 109171-. doi: 10.1016/j.cclet.2023.109171
8. [8]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
9. [9]
  Hao Cai , Xiaoyan Wu , Lei Jiang , Feng Yu , Yuxiang Yang , Yan Li , Xian Zhang , Jian Liu , Zijian Li , Hong Bi . Lysosome-targeted carbon dots with a light-controlled nitric oxide releasing property for enhanced photodynamic therapy. Chinese Chemical Letters, 2024, 35(4): 108946-. doi: 10.1016/j.cclet.2023.108946
10. [10]
  Wenkai Liu , Yanxian Hou , Weijian Liu , Ran Wang , Shan He , Xiang Xia , Chengyuan Lv , Hua Gu , Qichao Yao , Qingze Pan , Zehou Su , Danhong Zhou , Wen Sun , Jiangli Fan , Xiaojun Peng . Se-substituted pentamethine cyanine for anticancer photodynamic therapy mediated using the hot band absorption process. Chinese Chemical Letters, 2024, 35(12): 109631-. doi: 10.1016/j.cclet.2024.109631
11. [11]
  Du Liu , Yuyan Li , Hankun Zhang , Benhua Wang , Chaoyi Yao , Minhuan Lan , Zhanhong Yang , Xiangzhi Song . Three-in-one erlotinib-modified NIR photosensitizer for fluorescence imaging and synergistic chemo-photodynamic therapy. Chinese Chemical Letters, 2025, 36(2): 109910-. doi: 10.1016/j.cclet.2024.109910
12. [12]
  Liangliang Jia , Ye Hong , Xinyu He , Ying Zhou , Liujiao Ren , Hongjun Du , Bin Zhao , Bin Qin , Zhe Yang , Di Gao . Fighting hypoxia to improve photodynamic therapy-driven immunotherapy: Alleviating, exploiting and disregarding. Chinese Chemical Letters, 2025, 36(2): 109957-. doi: 10.1016/j.cclet.2024.109957
13. [13]
  Baoli Yin , Xinlin Liu , Zhe Li , Zhifei Ye , Youjuan Wang , Xia Yin , Sulai Liu , Guosheng Song , Shuangyan Huan , Xiao-Bing Zhang . Ratiometric NIR-Ⅱ fluorescent organic nanoprobe for imaging and monitoring tumor-activated photodynamic therapy. Chinese Chemical Letters, 2025, 36(5): 110119-. doi: 10.1016/j.cclet.2024.110119
14. [14]
  Xuejian Xing , Pan Zhu , E Pang , Shaojing Zhao , Yu Tang , Zheyu Hu , Quchang Ouyang , Minhuan Lan . D-A-D-structured boron-dipyrromethene with aggregation-induced enhanced phototherapeutic efficiency for near-infrared fluorescent and photoacoustic imaging-guided synergistic photodynamic and photothermal cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109452-. doi: 10.1016/j.cclet.2023.109452
15. [15]
  Lihua Ma , Song Guo , Zhi-Ming Zhang , Jin-Zhong Wang , Tong-Bu Lu , Xian-Shun Zeng . Sensitizing photoactive metal–organic frameworks via chromophore for significantly boosting photosynthesis. Chinese Chemical Letters, 2024, 35(5): 108661-. doi: 10.1016/j.cclet.2023.108661
16. [16]
  Yuequan Wang , Congtian Wu , Chengcheng Feng , Qin Chen , Zhonggui He , Shenwu Zhang , Cong Luo , Jin Sun . Spatiotemporally-controlled supramolecular hybrid nanoassembly enabling ferroptosis-augmented photodynamic immunotherapy of cancer. Chinese Chemical Letters, 2025, 36(3): 109902-. doi: 10.1016/j.cclet.2024.109902
17. [17]
  Yupeng Liu , Hui Wang , Songnan Qu . Review on near-infrared absorbing/emissive carbon dots: From preparation to multi-functional application. Chinese Chemical Letters, 2025, 36(5): 110618-. doi: 10.1016/j.cclet.2024.110618
18. [18]
  Jinyu Guo , Yandai Lin , Shaohua He , Yueqing Chen , Fenglu Li , Renjie Ruan , Gaoxing Pan , Hexin Nan , Jibin Song , Jin Zhang . Utilizing dual-responsive iridium(Ⅲ) complex for hepatocellular carcinoma: Integrating photoacoustic imaging with chemotherapy and photodynamic therapy. Chinese Chemical Letters, 2024, 35(9): 109537-. doi: 10.1016/j.cclet.2024.109537
19. [19]
  Kun-Heng Li , Hong-Yang Zhao , Dan-Dan Wang , Ming-Hui Qi , Zi-Jian Xu , Jia-Mi Li , Zhi-Li Zhang , Shi-Wen Huang . Mitochondria-targeted nano-AIEgens as a powerful inducer for evoking immunogenic cell death. Chinese Chemical Letters, 2024, 35(5): 108882-. doi: 10.1016/j.cclet.2023.108882
20. [20]
  Xinyue Lan , Junguang Liang , Churan Wen , Xiaolong Quan , Huimin Lin , Qinqin Xu , Peixian Chen , Guangyu Yao , Dan Zhou , Meng Yu . Photo-manipulated polyunsaturated fatty acid-doped liposomal hydrogel for flexible photoimmunotherapy. Chinese Chemical Letters, 2024, 35(4): 108616-. doi: 10.1016/j.cclet.2023.108616

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(880)
HTML views(31)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142