Synthesis of Self-Assembled Porphyrin Nanoparticle Photosensitizers

Wang, Dong; Niu, Lijuan; Qiao, Zeng-Ying; Cheng, Dong-Bing; Wang, Jiefei; Zhong, Yong; Bai, Feng; Wang, Hao; Fan, Hongyou

doi:10.1021/acsnano.8b01010

Synthesis of Self-Assembled Porphyrin Nanoparticle Photosensitizers

Journal Article · Tue Apr 03 00:00:00 EDT 2018 · ACS Nano

DOI:https://doi.org/10.1021/acsnano.8b01010· OSTI ID:1469627

Wang, Dong ^[1]; Niu, Lijuan ^[1]; Qiao, Zeng-Ying ^[2]; Cheng, Dong-Bing ^[2]; Wang, Jiefei ^[1]; ^[1]; Bai, Feng ^[1]; ^[2]; ^[3]

Henan Univ., Kaifeng (China). Key Lab. for Special Functional Materials of the Ministry of Education. Collaborative Innovation Center of Nano Functional Materials and Applications
National Center for Nanoscience and Technology (NCNST), Beijing (China). CAS Key Lab. for Biological Effects of Nanomaterials and Nanosafety
Univ. of New Mexico, Albuquerque, NM (United States). Dept. of Chemical and Biological Engineering; Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

The use of nanoparticles as a potential building block for photosensitizers has recently become a focus of interest in the field of photocatalysis and photodynamic therapy. Porphyrins and their derivatives are effective photosensitizers due to extended π-conjugated electronic structure, high molar absorption from visible to near-infrared spectrum, and high singlet oxygen quantum yields as well as chemical versatility. In this work, we report a synthesis of self-assembled porphyrin nanoparticle photosensitizers using zinc meso-tetra(4-pyridyl)porphyrin (ZnTPyP) through a confined noncovalent self-assembly process. Scanning electron microscopy reveals formation of monodisperse cubic nanoparticles. UV–vis characterizations reveal that optical absorption of the nanoparticles exhibits a red shift due to noncovalent self-assembly of porphyrins, which not only effectively increase intensity of light absorption but also extend light absorption broadly covering visible light for enhanced photodynamic therapy. Electron spin-resonance spectroscopy (ESR) studies show the resultant porphyrin nanoparticles release a high yield of singlet oxygen. Nitric oxide (NO) coordinates to central metal Zn ions to form stabilized ZnTPyP@NO nanoparticles. We show that under light irradiation ZnTPyP@NO nanoparticles release highly reactive peroxynitrite molecules that exhibit enhanced antibacterial photodynamic therapy (APDT) activity. Finally, the ease of the synthesis of self-assembled porphyrin nanoparticles and light-triggered release of highly reactive moieties represent a completely different photosensitizer system for APDT application.

View Accepted Manuscript (DOE)

Research Organization:: Henan Univ., Kaifeng (China); National Center for Nanoscience and Technology (NCNST), Beijing (China); Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

Sponsoring Organization:: National Natural Science Foundation of China (NSFC); Plan for Scientific Innovation Talent of Henan Province (China); Program for Changjiang Scholars and Innovative Research Team in University (China); USDOE National Nuclear Security Administration (NNSA); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: NA0003525

OSTI ID:: 1469627

Report Number(s):: SAND--2018-9735J; 667620

Journal Information:: ACS Nano, Journal Name: ACS Nano Journal Issue: 4 Vol. 12; ISSN 1936-0851

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (44)

Porphyrin-based photosensitizers for use in photodynamic therapy Sternberg, Ethan D.; Dolphin, David; Brückner, Christian Tetrahedron, Vol. 54, Issue 17 https://doi.org/10.1016/s0040-4020(98)00015-5	journal	April 1998
Antimicrobial photodynamic therapy: An overview Koshi, Elizabeth; Mohan, Aparna; Rajesh, S. Journal of Indian Society of Periodontology, Vol. 15, Issue 4 https://doi.org/10.4103/0972-124x.92563	journal	January 2011
Activatable Photoacoustic Nanoprobes for In Vivo Ratiometric Imaging of Peroxynitrite Zhang, Jianjian; Zhen, Xu; Upputuri, Paul Kumar Advanced Materials, Vol. 29, Issue 6 https://doi.org/10.1002/adma.201604764	journal	December 2016
Conjugation of Porphyrin to Nanohybrid Cerasomes for Photodynamic Diagnosis and Therapy of Cancer Liang, Xiaolong; Li, Xiaoda; Yue, Xiuli Angewandte Chemie, Vol. 123, Issue 49 https://doi.org/10.1002/ange.201103557	journal	October 2011
J-Aggregates: From Serendipitous Discovery to Supramolecular Engineering of Functional Dye Materials Würthner, Frank; Kaiser, Theo E.; Saha-Möller, Chantu R. Angewandte Chemie International Edition, Vol. 50, Issue 15 https://doi.org/10.1002/anie.201002307	journal	March 2011
Engineered Nanoparticles for Drug Delivery in Cancer Therapy Sun, Tianmeng; Zhang, Yu Shrike; Pang, Bo Angewandte Chemie International Edition https://doi.org/10.1002/anie.201403036	journal	October 2014
Interactions of Renal-Clearable Gold Nanoparticles with Tumor Microenvironments: Vasculature and Acidity Effects Yu, Mengxiao; Zhou, Chen; Liu, Li Angewandte Chemie International Edition, Vol. 56, Issue 15 https://doi.org/10.1002/anie.201612647	journal	March 2017
Large-Scale Production of Hierarchical TiO ₂ Nanorod Spheres for Photocatalytic Elimination of Contaminants and Killing Bacteria Bai, Hongwei; Liu, Zhaoyang; Liu, Lei Chemistry - A European Journal, Vol. 19, Issue 9 https://doi.org/10.1002/chem.201204013	journal	January 2013
The Mechanism of the Peroxynitrite–Carbon Dioxide Reaction Probed Using Tyrosine Zhang, Houwen; Squadrito, Giuseppe L.; Pryor, William A. Nitric Oxide, Vol. 1, Issue 4 https://doi.org/10.1006/niox.1997.0130	journal	August 1997
Self-assembly and alignment of semiconductor nanoparticles on cellulose nanocrystals Padalkar, Sonal; Capadona, Jeff R.; Rowan, Stuart J. Journal of Materials Science, Vol. 46, Issue 17 https://doi.org/10.1007/s10853-011-5518-4	journal	September 2011
Magnetic nanoparticles: material engineering and emerging applications in lithography and biomedicine Bao, Yuping; Wen, Tianlong; Samia, Anna Cristina S. Journal of Materials Science, Vol. 51, Issue 1 https://doi.org/10.1007/s10853-015-9324-2	journal	September 2015
Visible light photocatalytic antibacterial activity of Ni-doped and N-doped TiO2 on Staphylococcus aureus and Escherichia coli bacteria Ananpattarachai, Jirapat; Boonto, Yuphada; Kajitvichyanukul, Puangrat Environmental Science and Pollution Research, Vol. 23, Issue 5 https://doi.org/10.1007/s11356-015-4775-1	journal	June 2015
Porphyrin-based photosensitizers for use in photodynamic therapy Sternberg, Ethan D.; Dolphin, David; Brückner, Christian Tetrahedron, Vol. 54, Issue 17 https://doi.org/10.1016/S0040-4020(98)00015-5	journal	April 1998
Quantifying cellular oxidative stress by dichlorofluorescein assay using microplate reader11Mention of a trade name, proprietary product, or specific equipment does not constitute a guarantee by the United States Department of Agriculture and does not imply its approval to the exclusion of other products that may be suitable. Wang, Hong; Joseph, James A. Free Radical Biology and Medicine, Vol. 27, Issue 5-6 https://doi.org/10.1016/S0891-5849(99)00107-0	journal	September 1999
Structural characterization and macrophage immunomodulatory activity of a novel polysaccharide from Smilax glabra Roxb. Wang, Min; Yang, Xiao-bo; Zhao, Jing-wen Carbohydrate Polymers, Vol. 156 https://doi.org/10.1016/j.carbpol.2016.09.033	journal	January 2017
A lysosome-targeted BODIPY as potential NIR photosensitizer for photodynamic therapy Li, Mingle; Tian, Ruisong; Fan, Jiangli Dyes and Pigments, Vol. 147 https://doi.org/10.1016/j.dyepig.2017.07.048	journal	December 2017
Nitric oxide- and cisplatin-releasing silica nanoparticles for use against non-small cell lung cancer Munaweera, Imalka; Shi, Yi; Koneru, Bhuvaneswari Journal of Inorganic Biochemistry, Vol. 153 https://doi.org/10.1016/j.jinorgbio.2015.09.002	journal	December 2015
Comb-shaped, temperature-tunable and water-soluble porphyrin-based thermoresponsive copolymer for enhanced photodynamic therapy Liu, Changling; Li, Yanhui; Gao, Bo Materials Science and Engineering: C, Vol. 82 https://doi.org/10.1016/j.msec.2017.08.047	journal	January 2018
Solid tumor physiology and hypoxia-induced chemo/radio-resistance: Novel strategy for cancer therapy: Nitric oxide donor as a therapeutic enhancer Yasuda, Hiroyasu Nitric Oxide, Vol. 19, Issue 2 https://doi.org/10.1016/j.niox.2008.04.026	journal	September 2008
Nitric Oxide-Releasing Silica Nanoparticle-Doped Polyurethane Electrospun Fibers Koh, Ahyeon; Carpenter, Alexis W.; Slomberg, Danielle L. ACS Applied Materials & Interfaces, Vol. 5, Issue 16 https://doi.org/10.1021/am402044s	journal	July 2013
Mechanism of Carbon Dioxide-Catalyzed Oxidation of Tyrosine by Peroxynitrite Lymar, Sergei V.; Jiang, Qing; Hurst, James K. Biochemistry, Vol. 35, Issue 24 https://doi.org/10.1021/bi960331h	journal	January 1996
Nitric Oxide-Releasing Fumed Silica Particles: Synthesis, Characterization, and Biomedical Application Zhang, Huiping; Annich, Gail M.; Miskulin, Judiann Journal of the American Chemical Society, Vol. 125, Issue 17 https://doi.org/10.1021/ja0291538	journal	April 2003
Sunlight-Triggered Nanoparticle Synergy: Teamwork of Reactive Oxygen Species and Nitric Oxide Released from Mesoporous Organosilica with Advanced Antibacterial Activity Gehring, Julia; Trepka, Bastian; Klinkenberg, Nele Journal of the American Chemical Society, Vol. 138, Issue 9 https://doi.org/10.1021/jacs.5b12073	journal	February 2016
Selective Visualization of the Endogenous Peroxynitrite in an Inflamed Mouse Model by a Mitochondria-Targetable Two-Photon Ratiometric Fluorescent Probe Cheng, Dan; Pan, Yue; Wang, Lu Journal of the American Chemical Society, Vol. 139, Issue 1 https://doi.org/10.1021/jacs.6b10508	journal	December 2016
Porous One-Dimensional Nanostructures through Confined Cooperative Self-Assembly Bai, Feng; Sun, Zaicheng; Wu, Huimeng Nano Letters, Vol. 11, Issue 12 https://doi.org/10.1021/nl203598n	journal	December 2011
Photodynamic therapy for cancer Dolmans, Dennis E. J. G. J.; Fukumura, Dai; Jain, Rakesh K. Nature Reviews Cancer, Vol. 3, Issue 5 https://doi.org/10.1038/nrc1071	journal	May 2003
Disease tolerance and immunity in host protection against infection Soares, Miguel P.; Teixeira, Luis; Moita, Luis F. Nature Reviews Immunology, Vol. 17, Issue 2 https://doi.org/10.1038/nri.2016.136	journal	January 2017
The role of porphyrin chemistry in tumor imaging and photodynamic therapy Ethirajan, Manivannan; Chen, Yihui; Joshi, Penny Chem. Soc. Rev., Vol. 40, Issue 1 https://doi.org/10.1039/B915149B	journal	January 2011
High-yield halide-free synthesis of biocompatible Au nanoplates Wang, Guoqing; Tao, Shengyang; Liu, Yiding Chemical Communications, Vol. 52, Issue 2 https://doi.org/10.1039/C5CC07957H	journal	January 2016
Noble metal–metal oxide nanohybrids with tailored nanostructures for efficient solar energy conversion, photocatalysis and environmental remediation Liu, Xueqin; Iocozzia, James; Wang, Yang Energy & Environmental Science, Vol. 10, Issue 2 https://doi.org/10.1039/C6EE02265K	journal	January 2017
Mesoporous silica nanoparticles functionalized with an oxygen-sensing probe for cell photodynamic therapy: potential cancer theranostics Cheng, Shih-Hsun; Lee, Chia-Hung; Yang, Chung-Shi Journal of Materials Chemistry, Vol. 19, Issue 9 https://doi.org/10.1039/b816636f	journal	January 2009
Monodisperse porous nanodiscs with fluorescent and crystalline wall structure Bai, Feng; Wu, Huimeng; Haddad, Raid E. Chemical Communications, Vol. 46, Issue 27 https://doi.org/10.1039/c002936j	journal	January 2010
Supramolecular polymeric micelles by the host–guest interaction of star-like calix[4]arene and chlorin e6 for photodynamic therapy Tu, Chunlai; Zhu, Lijuan; Li, Pingping Chemical Communications, Vol. 47, Issue 21 https://doi.org/10.1039/c0cc05662f	journal	January 2011
The role of nitric oxide in inflammatory reactions: Nitric oxide: control of immune response Tripathi, Parul; Tripathi, Prashant; Kashyap, Luv FEMS Immunology & Medical Microbiology, Vol. 51, Issue 3 https://doi.org/10.1111/j.1574-695X.2007.00329.x	journal	September 2007
Porphyrin and Nonporphyrin Photosensitizers in Oncology: Preclinical and Clinical Advances in Photodynamic Therapy O’Connor, Aisling E.; Gallagher, William M.; Byrne, Annette T. Photochemistry and Photobiology, Vol. 85, Issue 5 https://doi.org/10.1111/j.1751-1097.2009.00585.x	journal	September 2009
DNA deaminating ability and genotoxicity of nitric oxide and its progenitors Wink, D.; Kasprzak, K.; Maragos, C. Science, Vol. 254, Issue 5034 https://doi.org/10.1126/science.1948068	journal	November 1991
Thirty Years of Saying NO: Sources, Fate, Actions, and Misfortunes of the Endothelium-Derived Vasodilator Mediator Vanhoutte, Paul M.; Zhao, Yingzi; Xu, Aimin Circulation Research, Vol. 119, Issue 2 https://doi.org/10.1161/CIRCRESAHA.116.306531	journal	July 2016
Phenotype-Specific Treatment of Heart Failure With Preserved Ejection Fraction: A Multiorgan Roadmap Shah, Sanjiv J.; Kitzman, Dalane W.; Borlaug, Barry A. Circulation, Vol. 134, Issue 1 https://doi.org/10.1161/CIRCULATIONAHA.116.021884	journal	July 2016
Nitric Oxide-Releasing Biomaterials for Biomedical Applications Zhou, Xin; Zhang, Jimin; Feng, Guowei Current Medicinal Chemistry, Vol. 23, Issue 24 https://doi.org/10.2174/0929867323666160729104647	journal	August 2016
Chemosensitization of Cancer by Nitric Oxide Sullivan, Richard; Graham, Charles Current Pharmaceutical Design, Vol. 14, Issue 11 https://doi.org/10.2174/138161208784246225	journal	April 2008
Nitrosative stress in cancer therapy Hirst, David, G. Frontiers in Bioscience, Vol. 12, Issue 8-12 https://doi.org/10.2741/2322	journal	January 2007
Photodynamic therapy of cancer: An update Agostinis, Patrizia; Berg, Kristian; Cengel, Keith A. CA: A Cancer Journal for Clinicians, Vol. 61, Issue 4 https://doi.org/10.3322/caac.20114	journal	May 2011
Antimicrobial photodynamic therapy: An overview Koshi, Elizabeth; Mohan, Aparna; Rajesh, S. Journal of Indian Society of Periodontology, Vol. 15, Issue 4 https://doi.org/10.4103/0972-124X.92563	journal	January 2011
The potential of nitric oxide releasing therapies as antimicrobial agents Schairer, David O.; Chouake, Jason S.; Nosanchuk, Joshua D. Virulence, Vol. 3, Issue 3 https://doi.org/10.4161/viru.20328	journal	May 2012

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