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

Yang Liu; Nan Song; Li Chen; Zhi-Gang Xie

doi:10.1007/s10118-018-2096-9

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

ARTICLES | Updated：2021-02-18

- BODIPY@Ir(Ⅲ) Complexes Assembling Organic Nanoparticles for Enhanced Photodynamic Therapy
- BODIPY@Ir(Ⅲ) Complexes Assembling Organic Nanoparticles for Enhanced Photodynamic Therapy
- Chinese Journal of Polymer Science 2018年36卷第3期页码：417-424
- Affiliations：
  
  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
- Author bio：
  
  Li Chen, E-mail chenl686@nenu.edu.cn
  Zhi-Gang Xie, E-mail xiez@ciac.ac.cn
- Funds：
  
  Electronic supplementary information (ESI) is available free of charge in the online version of this article at: https://doi.org/10.1007/s10118-018-2096-9.
- DOI：10.1007/s10118-018-2096-9
  中图分类号：
- 收稿：2017-09-27，
  
  录用：2017-11-23，
  
  网络首发：2017-12-27，
  
  纸质出版：2018-03-05
- Accepted：
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Yang Liu, Nan Song, Li Chen, 等. BODIPY@Ir(Ⅲ) Complexes Assembling Organic Nanoparticles for Enhanced Photodynamic Therapy[J]. Chinese Journal of Polymer Science, 2018,36(3):417-424.

Yang Liu, Nan Song, Li Chen, et al. BODIPY@Ir(Ⅲ) Complexes Assembling Organic Nanoparticles for Enhanced Photodynamic Therapy[J]. Chinese Journal of Polymer Science, 2018, 36(3): 417-424.
Yang Liu, Nan Song, Li Chen, 等. 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.

Yang Liu, Nan Song, Li Chen, et al. 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.

摘要

Abstract

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.

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Keywords

references

H. Li , P. Wang , Y. Deng , M. Zeng , Y. Tang , W. H. Zhu , Y. Cheng . Combination of active targeting, enzyme-triggered release and fluorescent dye into gold nanoclusters for endomicroscopy-guided photothermal/photodynamic therapy to pancreatic ductal adenocarcinoma . Biomaterials , 2017 . 139 30 - 38 . DOI: 10.1016/j.biomaterials.2017.05.030 http://doi.org/10.1016/j.biomaterials.2017.05.030 .

X. Li , M. Gao , K. Xin , L. Zhang , D. Ding , D. Kong , Z. Wang , Y. Shi , F. Kiessling , T. Lammers , J. Cheng , Y. Zhao . Singlet oxygen-responsive micelles for enhanced photodynamic therapy . J. Control. Release , 2017 . 260 12 - 21 . DOI: 10.1016/j.jconrel.2017.05.025 http://doi.org/10.1016/j.jconrel.2017.05.025 .

I. A. P. Linares , K. T. de Oliveira , J. R. Perussi . Chlorin derivatives sterically-prevented from self-aggregation with high antitumor activity for photodynamic therapy . Dyes Pigm. , 2017 . 145 518 - 527 . DOI: 10.1016/j.dyepig.2017.06.011 http://doi.org/10.1016/j.dyepig.2017.06.011 .

H. Xiong , D. Zhou , X. Zheng , Y. Qi , Y. Wang , X. Jing , Y. Huang . Stable amphiphilic supramolecular self-assembly based on cyclodextrin and carborane for the efficient photodynamic therapy . Chem. Commun. , 2017 . 53 3422 - 3425 . DOI: 10.1039/C6CC10059G http://doi.org/10.1039/C6CC10059G .

E. Du , X. Hu , S. Roy , P. Wang , K. Deasy , T. Mochizuki , Y. Zhang . Taurine-modified Ru(ii)-complex targets cancerous brain cells for photodynamic therapy . Chem. Commun. , 2017 . 53 6033 - 6036 . DOI: 10.1039/C7CC03337K http://doi.org/10.1039/C7CC03337K .

B. Gu , W. Wu , G. Xu , G. Feng , F. Yin , P. H. J. Chong , J. Qu , K. T. Yong , B. Liu . Precise two-photon photodynamic therapy using an efficient photosensitizer with aggregationinduced emission characteristics . Adv. Mater. , 2017 . 29 ( 28 ): DOI: 10.1002/adma.201701076 http://doi.org/10.1002/adma.201701076 .

L. Huang , Z. Li , Y. Zhao , J. Yang , Y. Yang , A. I. Pendharkar , Y. Zhang , S. Kelmar , L. Chen , W. Wu , J. Zhao , G. Han . Enhancing photodynamic therapy through resonance energy transfer constructed near-Infrared photosensitized nanoparticles . Adv. Mater. , 2017 . 29 ( 28 ): DOI: 10.1002/adma.201604789 http://doi.org/10.1002/adma.201604789 .

C. Yue , Y. Yang , J. Song , G. Alfranca , C. Zhang , Q. Zhang , T. Yin , F. Pan , J. M. de la Fuente , D. Cui . Mitochondriatargeting near-infrared light-triggered thermosensitive liposomes for localized photothermal and photodynamic ablation of tumors combined with chemotherapy . Nanoscale , 2017 . 9 11103 - 11118 . DOI: 10.1039/C7NR02193C http://doi.org/10.1039/C7NR02193C .

Y. Zheng , H. Lu , Z. Jiang , Y. Guan , J. Zou , X. Wang , R. Cheng , H. Gao . Low-power white light triggered AIE polymer nanoparticles with high ROS quantum yield for mitochondria-targeted and image-guided photodynamic therapy . J. Mater. Chem. B , 2017 . 5 6277 - 6281 . http://pubs.rsc.org/en/content/articlelanding/2017/tb/c7tb01443k#! http://pubs.rsc.org/en/content/articlelanding/2017/tb/c7tb01443k#! , .

Y. Li , X. Zheng , X. Zhang , S. Liu , Q. Pei , M. Zheng , Z. Xie . Porphyrin-based carbon dots for photodynamic therapy of hepatoma . Adv. Healthc. Mater. , 2017 . 6 ( 1 ): DOI: 10.1002/adhm.201600924 http://doi.org/10.1002/adhm.201600924 .

W. Liu , Y. M. Wang , Y. H. Li , S. J. Cai , X. B. Yin , X. W. He , Y. K. Zhang . Fluorescent imaging-guided chemotherapyand-photodynamic dual therapy with nanoscale porphyrin metal-organic framework . Small , 2017 . 13 ( 17 ): DOI: 10.1002/smll.201603459 http://doi.org/10.1002/smll.201603459 .

L. Rui , Y. Xue , Y. Wang , Y. Gao , W. Zhang . A mitochondria-targeting supramolecular photosensitizer based on pillararene for photodynamic therapy . Chem. Commun. , 2017 . 53 3126 - 3129 . DOI: 10.1039/C7CC00950J http://doi.org/10.1039/C7CC00950J .

W. Zhang , W. Lin , X. Zheng , S. He , Z. Xie . Comparing effects of redox sensitivity of organic nanoparticles to photodynamic activity . Chem. Mater. , 2017 . 29 1856 - 1863 . DOI: 10.1021/acs.chemmater.7b00207 http://doi.org/10.1021/acs.chemmater.7b00207 .

X. Zheng , L. Wang , Q. Pei , S. He , S. Liu , Z. Xie . Metal-organic framework@porous organic polymer nanocomposite for photodynamic therapy . Chem. Mater. , 2017 . 29 2374 - 2381 . DOI: 10.1021/acs.chemmater.7b00228 http://doi.org/10.1021/acs.chemmater.7b00228 .

M. Isik , R. Guliyev , S. Kolemen , Y. Altay , B. Senturk , T. Tekinay , E. U. Akkaya . Designing an intracellular fluorescent probe for glutathione:two modulation sites for selective signal transduction . Org. Lett. , 2014 . 16 3260 - 3263 . DOI: 10.1021/ol501272z http://doi.org/10.1021/ol501272z .

M. Isik , T. Ozdemir , I. S. Turan , S. Kolemen , E. U. Akkaya . Chromogenic and fluorogenic sensing of biological thiols in aqueous solutions using BODIPY-based reagents . Org. Lett. , 2013 . 15 216 - 219 . DOI: 10.1021/ol303306s http://doi.org/10.1021/ol303306s .

C. Göl , M. Malkoç , S. Yeşilot , M. Durmuş . Novel zinc(Ⅱ) phthalocyanine conjugates bearing different numbers of BODIPY and iodine groups as substituents on the periphery . Dyes Pigm. , 2014 . 111 81 - 90 . DOI: 10.1016/j.dyepig.2014.06.003 http://doi.org/10.1016/j.dyepig.2014.06.003 .

B. Kim , B. Sui , X. Yue , S. Tang , M. G. Tichy , K. D. Belfield . In vitro photodynamic studies of a BODIPY-based photosensitizer . Eur. J. Org. Chem. , 2017 . ( 1 ): 25 - 28 . https://link.springer.com/content/pdf/10.1007/BF02590221.pdf https://link.springer.com/content/pdf/10.1007/BF02590221.pdf , .

W. Wang , L. Wang , Z. Li , Z. Xie . BODIPY-containing nanoscale metal-organic frameworks for photodynamic therapy . Chem. Commun. , 2016 . 52 5402 - 5405 . DOI: 10.1039/C6CC01048B http://doi.org/10.1039/C6CC01048B .

Z. Guo , Y. Zou , H. He , J. Rao , S. Ji , X. Cui , H. Ke , Y. Deng , H. Yang , C. Chen , Y. Zhao , H. Chen . Bifunctional platinated nanoparticles for photoinduced tumor ablation . Adv. Mater. , 2016 . 46 ( 28 ): 10155 - 10164 . http://doi.wiley.com/10.1002/adma.201602738 http://doi.wiley.com/10.1002/adma.201602738 , .

Y. Liu , Z. Li , L. Chen , Z. Xie . Near infrared BODIPY-platinum conjugates for imaging, photodynamic therapy and chemotherapy . Dyes Pigm. , 2017 . 141 5 - 12 . DOI: 10.1016/j.dyepig.2017.01.075 http://doi.org/10.1016/j.dyepig.2017.01.075 .

Y. Cakmak , S. Kolemen , S. Duman , Y. Dede , Y. Dolen , B. Kilic , Z. Kostereli , L. T. Yildirim , A. L. Dogan , D. Guc , E. U. Akkaya . Designing excited states:theory-guided access to efficient photosensitizers for photodynamic action . Angew. Chem. , 2011 . 50 11937 - 11941 . DOI: 10.1002/anie.v50.50 http://doi.org/10.1002/anie.v50.50 .

N. Epelde-Elezcano , E. Palao , H. Manzano , A. PrietoCastaneda , A. R. Agarrabeitia , A. Tabero , A. Villanueva , S. de la Moya , I. Lopez-Arbeloa , V. Martinez-Martinez , M. J. Ortiz . Rational design of advanced photosensitizers based on orthogonal BODIPY dimers to finely modulate singlet oxygen generation . Chem. Eur. J. , 2017 . 23 4837 - 4848 . DOI: 10.1002/chem.v23.20 http://doi.org/10.1002/chem.v23.20 .

T. Ozdemir , J. L. Bila , F. Sozmen , L. T. Yildirim , E. U. Akkaya . Orthogonal Bodipy trimers as photosensitizers for photodynamic action . Org. Lett. , 2016 . 18 4821 - 4823 . DOI: 10.1021/acs.orglett.6b02418 http://doi.org/10.1021/acs.orglett.6b02418 .

W. Wu , X. Cui , J. Zhao . Hetero BODIPY-dimers as heavy atom-free triplet photosensitizers showing a long-lived triplet excited state for triplet-triplet annihilation upconversion . Chem. Commun. , 2013 . 49 9009 - 9011 . DOI: 10.1039/c3cc45470c http://doi.org/10.1039/c3cc45470c .

X. F. Zhang , X. Yang . Photosensitizer that selectively generates singlet oxygen in nonpolar environments:photophysical mechanism and efficiency for a covalent BODIPY dimer . J. Phys. Chem. B , 2013 . 117 9050 - 9055 . DOI: 10.1021/jp405102m http://doi.org/10.1021/jp405102m .

C. Mari , H. Huang , R. Rubbiani , M. Schulze , F. Würthner , H. Chao , G. Gasser . Evaluation of perylene bisimide-based RuⅡand IrⅢ complexes as photosensitizers for photodynamic therapy . Eur. J. Inorg. Chem. , 2017 . 2017 1745 - 1752 . http://www.cjps.org/EN/abstract/abstract13454.shtml http://www.cjps.org/EN/abstract/abstract13454.shtml , .

L. Wang , H. Yin , P. Cui , M. Hetu , C. Wang , S. Monro , R. D. Schaller , C. G. Cameron , B. Liu , S. Kilina , S. A. McFarland , W. Sun . Near-infrared-emitting heteroleptic cationic iridium complexes derived from 2, 3-diphenylbenzo[ g ]quinoxaline as in vitro theranostic photodynamic therapy agents . Dalton Trans , 2017 . 46 8091 - 8103 . DOI: 10.1039/C7DT00913E http://doi.org/10.1039/C7DT00913E .

H. Xiang , H. Chen , H. P. Tham , S. Z. F. Phua , J. G. Liu , Y. Zhao . Cyclometalated iridium(Ⅲ)-complex-based micelles for glutathione-responsive targeted chemotherapy and photodynamic therapy . ACS Appl. Mater. Interfaces , 2017 . 9 27553 - 27562 . DOI: 10.1021/acsami.7b09506 http://doi.org/10.1021/acsami.7b09506 .

Y. Zheng , L. He , D. Y. Zhang , C. P. Tan , L. N. Ji , Z. W. Mao . Mixed-ligand iridium(Ⅲ) complexes as photodynamic anticancer agents . Dalton Trans. , 2017 . 46 11395 - 11407 . DOI: 10.1039/C7DT02273E http://doi.org/10.1039/C7DT02273E .

J. Liu , C. Jin , B. Yuan , X. Liu , Y. Chen , L. Ji , H. Chao . Selectively lighting up two-photon photodynamic activity in mitochondria with AIE-active iridium(Ⅲ) complexes . Chem. Commun. , 2017 . 53 2052 - 2055 . DOI: 10.1039/C6CC10015E http://doi.org/10.1039/C6CC10015E .

L. K. McKenzie , I. V. Sazanovich , E. Baggaley , M. Bonneau , V. Guerchais , J. A. Williams , J. A. Weinstein , H. E. Bryant . Metal complexes for two-photon photodynamic therapy:a cyclometallated iridium complex induces two-photon photosensitization of cancer cells under near-IR light . Chem. Eur. J. , 2017 . 23 234 - 238 . DOI: 10.1002/chem.v23.2 http://doi.org/10.1002/chem.v23.2 .

J. S. Nam , M. G. Kang , J. Kang , S. Y. Park , S. J. Lee , H. T. Kim , J. K. Seo , O. H. Kwon , M. H. Lim , H. W. Rhee , T. H. Kwon . Endoplasmic reticulum-localized iridium(Ⅲ) complexes as efficient photodynamic therapy agents via protein modifications . J. Am. Chem. Soc. , 2016 . 138 10968 - 10977 . DOI: 10.1021/jacs.6b05302 http://doi.org/10.1021/jacs.6b05302 .

K. Qiu , M. Ouyang , Y. Liu , H. Huang , C. Liu , Y. Chen , L. Ji , H. Chao . Two-photon photodynamic ablation of tumor cells by mitochondria-targeted iridium(Ⅲ) complexes in aggregate states . J. Mater. Chem. B , 2017 . 5 5488 - 5498 . DOI: 10.1039/C7TB00731K http://doi.org/10.1039/C7TB00731K .

X. Tian , Y. Zhu , M. Zhang , L. Luo , J. Wu , H. Zhou , L. Guan , G. Battaglia , Y. Tian . Localization matters:a nuclear targeting two-photon absorption iridium complex in photodynamic therapy . Chem. Commun. , 2017 . 53 3303 - 3306 . DOI: 10.1039/C6CC09470H http://doi.org/10.1039/C6CC09470H .

N. Deligonul , A. R. Browne , J. A. Golen , A. L. Rheingold , T. G. Gray . Cyclometalated iridium(Ⅲ) complexes of azadipyrromethene chromophores . Organometallics , 2014 . 33 637 - 643 . DOI: 10.1021/om4007032 http://doi.org/10.1021/om4007032 .

J. Zhou , L. Gai , Z. Zhou , J. Mack , K. Xu , J. Zhao , H. Qiu , K. S. Chan , Z. Shen . Highly efficient near IR photosensitizers based on Ir-C bonded porphyrin-aza-BODIPY conjugates . RSC Adv. , 2016 . 6 72115 - 72120 . DOI: 10.1039/C6RA10131C http://doi.org/10.1039/C6RA10131C .

P. Majumdar , X. Yuan , S. Li , B. Le Guennic , J. Ma , C. Zhang , D. Jacquemin , J. Zhao . 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. Mater. Chem. B , 2014 . 2 2838 - 2854 . DOI: 10.1039/C4TB00284A http://doi.org/10.1039/C4TB00284A .

E. Palao , R. Sola-Llano , A. Tabero , H. Manzano , A. R. Agarrabeitia , A. Villanueva , I. Lopez-Arbeloa , V. Martinez-Martinez , M. J. Ortiz . Acetylacetonate BODIPY-biscyclometalated iridium(Ⅲ) complexes:effective strategy towards smarter fluorescent photosensitizer agents . Chem. Eur. J. , 2017 . 23 10139 - 10147 . DOI: 10.1002/chem.v23.42 http://doi.org/10.1002/chem.v23.42 .

J. Sun , F. Zhong , X. Yi , J. Zhao . 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 . Inorg. Chem. , 2013 . 52 6299 - 6310 . DOI: 10.1021/ic302210b http://doi.org/10.1021/ic302210b .

L. Tabrizi , H. Chiniforoshan . New cyclometalated Ir(Ⅲ) complexes with NCN pincer and meso-phenylcyanamide BODIPY ligands as efficient photodynamic therapy agents . RSC Adv. , 2017 . 7 34160 - 34169 . DOI: 10.1039/C7RA05579J http://doi.org/10.1039/C7RA05579J .

R. F. Khairoutdinov , L. V. Doubova , R. C. Haddon , L. Saraf . Persistent photoconductivity in chemically modified single-wall carbon nanotubes . J. Phys. Chem. B , 2004 . 108 19976 - 19981 . DOI: 10.1021/jp046495m http://doi.org/10.1021/jp046495m .

Z. Li , M. Zheng , X. Guan , Z. Xie , Y. Huang , X. Jing . Unadulterated BODIPY-dimer nanoparticles with high stability and good biocompatibility for cellular imaging . Nanoscale , 2014 . 6 5662 - 5665 . DOI: 10.1039/C4NR00521J http://doi.org/10.1039/C4NR00521J .

Y. Liu , N. Song , L. Chen , Z. Xie . Triple-BODIPY organic nanoparticles with particular fluorescence emission . Dyes Pigm. , 2017 . 147 241 - 245 . DOI: 10.1016/j.dyepig.2017.08.026 http://doi.org/10.1016/j.dyepig.2017.08.026 .

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