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Anti-tumor evaluation of a novel methoxyphenyl substituted chlorin photosensitizer for photodynamic therapy
Abstract
Photodynamic therapy (PDT) is a non-invasive and innovative therapeutic approach which has been increasingly applied in clinical cancer therapy. As the central element of PDT, the development of novel photosensitizers (PSs) with longer absorption wavelength, proper lipophilic/hydrophilic profiles, target tissue selectivity, and higher photo-/lowest dark-cytotoxicity is a challenging task. Previously, we designed and synthesized a series of novel long-wavelength chlorin e6 (Ce6)-based PSs via introducing aromatic groups to the vinyl of Ce6 skeleton. The new formed compounds with π-extension system exhibited improved photodynamic effects and spectral characteristics. Among these π-conjugated chlorin PSs, (E)-3 2-(4-methoxyphenyl)-chlorin e6, named A15, was expected to be a potent antitumor candidate as a PDT agent due to its good photobiological properties. Herein, in this work, we evaluated the effectiveness of A15 in cancer PDT. In vitro, a novel rare earth probe, ATTA-Eu 3+ was applied to detect the singlet oxygen (1 O 2) production of A15 in solution and human hepatoma HepG2 cells, respectively. Moreover, A15 exhibited strong phototoxicity and weak dark cytotoxity to HepG2 cells. In H22 tumor bearing mice, A15 showed excellent tumor accumulation ability via i.v. administration and induced tumor regression, followed by laser treatment. These results indicated that A15 is a potential novel π-extension chlorin-type PS for PDT applications.
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“A derivate of Ce6 ((E)-32-(4-methoxyphenyl)-chlorin e6), processed from Spirulina powder, exhibited phototoxicity against HepG2 cells, whose viability was only 10% at 1 μM [145].”
From Emerging Applications of Chlorella sp. and Spirulina (Arthrospira) sp. (2023) · cites this paper as [145]
Citations
Cites
O’Connor, A. E., Gallagher, W. M., & Byrne, A. T. (2009) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2009.00585.x · Cited by 1,191
Self-assembled single-atom nanozyme for enhanced photodynamic therapy treatment of tumor
Wang, D., Wu, H., Phua, S. Z. F., Yang, G., Lim, W. Q., Gu, L., Qian, C., Wang, H., Guo, Z. G., Chen, H., et al. (2020) · Nature Communications · doi:10.1038/s41467-019-14199-7 · Cited by 545
Naito, S., von Eschenbach, A. C., Giavazzi, R., et al. (1986) · PubMed · Cited by 521
Mallidi, S., Anbil, S. R., Bulin, A., Obaid, G., Ichikawa, M., & Hasan, T. G. (2016) · Theranostics · doi:10.7150/thno.16183 · Cited by 453
Advance in Photosensitizers and Light Delivery for Photodynamic Therapy
Yoon, I., Li, J., & Shim, Y. K. (2013) · Clinical Endoscopy · doi:10.5946/ce.2013.46.1.7 · Cited by 438
Azzouzi, A.-R., Vincendeau, S., Barret, É., Cicco, A., Kleinclauss, F., van der Poel, H. G., Stief, C. G., Rassweiler, J., Salomon, G., Solsona, E., et al. (2016) · The Lancet Oncology · doi:10.1016/s1470-2045(16)30661-1 · Cited by 346
Singlet oxygen generation by photodynamic agents
Fernandez, J. M., Bilgin, M., & Grossweiner, L. I. (1997) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/s1011-1344(96)07349-6 · Cited by 301
Garland, M. J., Cassidy, C. M., Woolfson, D., & Donnelly, R. F. (2009) · Future Medicinal Chemistry · doi:10.4155/fmc.09.55 · Cited by 207
Ohyashiki, T., Nunomura, M., & Katoh, T. (1999) · Biochimica et Biophysica Acta (BBA) - Biomembranes · doi:10.1016/s0005-2736(99)00119-4 · Cited by 133
Recent developments in the detection of singlet oxygen with molecular spectroscopic methods
Wu, H., Song, Q., Ran, G., Xiao-Mu, L. U., & Xu, B. (2010) · TrAC Trends in Analytical Chemistry · doi:10.1016/j.trac.2010.08.009 · Cited by 129
Hadjur, C., Lange, N., Rebstein, J., Monnier, P., van den Bergh, H., & Wagnières, G. (1998) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/s1011-1344(98)00177-8 · Cited by 120
Epelde‐Elezcano, N., Palao, E., Manzano, H., Prieto‐Castañeda, A., Agarrabeitia, A. R., Tabero, A., Villanueva, Á., Cerero, S. D. L. M., López‐Arbeloa, Í., Martínez‐Martínez, V., et al. (2017) · Chemistry - A European Journal · doi:10.1002/chem.201605822 · Cited by 110
Hernández, I. B., Yu, Y., OSSENDORP, F. A., Korbelik, M., & Oliveira, S. (2020) · Journal of Clinical Medicine · doi:10.3390/jcm9020333 · Cited by 109
Xu, H., Tian, H., Jiang, W. H., et al. (2018) · Small · doi:10.1002/smll.201802994 · Cited by 106
Self-Assembled Chlorin e6 Conjugated Chondroitin Sulfate Nanodrug for Photodynamic Therapy
Li, F., & Na, K. (2011) · Biomacromolecules · doi:10.1021/bm200115v · Cited by 104
A new europium chelate-based phosphorescence probe specific for singlet oxygen
Song, B., Wang, G., & Yuan, J. (2005) · Chemical Communications · doi:10.1039/b503980k · Cited by 101
Li, X., Feng, X., Sun, C., Liu, Y., Zhao, Q., & Wang, S. (2019) · Journal of Controlled Release · doi:10.1016/j.jconrel.2019.12.042 · Cited by 80
Zhu, Y., Jia, H., Chen, Z., & Wu, F. (2017) · Nanoscale · doi:10.1039/c7nr02279d · Cited by 77
Cao, W., Liu, B., Xia, F., Duan, M., Hong, Y., Niu, J., Wang, L., Liu, Y., Li, C., & Cui, D. (2019) · Nanoscale · doi:10.1039/c9nr07947e · Cited by 73
Self-citationA new fluorescence method to detect singlet oxygen inside phospholipid model membranes
Woźniak, M., Tanfani, F., Bertoli, E., et al. (1991) · Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism · doi:10.1016/0005-2760(91)90304-z · Cited by 68
Syntheses and Cellular Investigations of 173-, 152-, and 131-Amino Acid Derivatives of Chlorin e6
Jinadasa, R. G. W., Hu, X., Vicente, M. G. H., & Smith, K. M. (2011) · Journal of Medicinal Chemistry · doi:10.1021/jm2005139 · Cited by 65
Li, Z., Wang, C., Deng, H., Wu, J., Huang, H., Sun, R., Zhang, H., Xiong, X., & Feng, M. (2019) · Advanced Science · doi:10.1002/advs.201802057 · Cited by 57
Water-Soluble Chlorin/Arylaminoquinazoline Conjugate for Photodynamic and Targeted Therapy
Otvagin, V. F., Kuzmina, N. S., Krylova, L. V., Volovetsky, A. B., Nyuchev, A. V., Gavryushin, A. E., Meshkov, I. N., Gorbunova, Y. G., Romanenko, Y. V., Койфман, О. И., et al. (2019) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.9b01294 · Cited by 52
New unsymmetrical squaraine dyes derived from imidazo[1,5-a]pyridine
Prostota, Y. O., Kachkovsky, O. D., Reis, L. V. D., et al. (2012) · Dyes and Pigments · doi:10.1016/j.dyepig.2012.10.006 · Cited by 47
Chlorin e6 loaded lactoferrin nanoparticles for enhanced photodynamic therapy
Adimoolam, M. G., Vijayalakshmi, A., Nalam, M. R., & Manorama, S. V. (2017) · Journal of Materials Chemistry B · doi:10.1039/c7tb02599h · Cited by 44
Donzello, M. P., Viola, E., Giustini, M., et al. (2012) · Dalton Transactions · doi:10.1039/c2dt12381a · Cited by 43
Synthesis and Characterization of New Fluorene-Based Singlet Oxygen Sensitizers
Belfield, K. D., Corredor, C. C., Morales, A. R., Dessources, M. A., & Hernandez, F. E. (2005) · Journal of Fluorescence · doi:10.1007/s10895-005-0008-1 · Cited by 39
Cellular Changes, Molecular Pathways and the Immune System Following Photodynamic Treatment
Skupin-Mrugalska, P., Sobotta, Ł., Kucińska, M., et al. (2014) · Current Medicinal Chemistry · doi:10.2174/0929867321666140826120300 · Cited by 39
Synthesis of novel long wavelength cationic chlorins via stereoselective aldol-like condensation
Li, J., Wang, J. J., Yoon, I., et al. (2012) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2012.01.088 · Cited by 37
Jung, Y., Klein, O. J., Wang, H., & Evans, C. L. (2016) · Scientific Reports · doi:10.1038/srep27017 · Cited by 32
Synthesis and photocytotoxic activity of new chlorin–polyamine conjugates
Garcia, G., Sol, V., Lamarche, F., et al. (2006) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2006.03.044 · Cited by 30
Dinçalp, H., Kızılok, Ş., & İçli, S. (2014) · Journal of Fluorescence · doi:10.1007/s10895-014-1372-5 · Cited by 23
Semi-synthesis and PDT activities of a new amphiphilic chlorin derivative
Moritz, M. N. D. O., Gonçalves, J. L. S., Linares, I. A. P., et al. (2016) · Photodiagnosis and Photodynamic Therapy · doi:10.1016/j.pdpdt.2016.10.005 · Cited by 21
Yao, J., Zhang, W., Sheng, C., et al. (2007) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2007.10.086 · Cited by 19
Muddineti, O. S., Rompicharla, S. V. K., Kumari, P., Bhatt, H., Ghosh, B., & Biswas, S. (2019) · Photodiagnosis and Photodynamic Therapy · doi:10.1016/j.pdpdt.2019.101633 · Cited by 19
Syntheses and PDT activity of new mono- and di-conjugated derivatives of chlorin e6
Chen, H., Humble, S. W., Jinadasa, R. G. W., Zhou, Z., Nguyen, A. L., Vicente, M. G. H., & Smith, K. M. (2017) · Journal of Porphyrins and Phthalocyanines · doi:10.1142/s1088424617500262 · Cited by 17
Feng, C., Chen, L., Lu, Y., Liu, J., Liang, S., Lin, Y., Li, Y., & Dong, C. (2019) · Frontiers in Chemistry · doi:10.3389/fchem.2019.00853 · Cited by 16
Self-citationSynthesis and in vitro phototoxicity of novel π-extension derivatives of chlorin e6
Cao, L., Guo, X., Wang, L., Wang, S., Li, Y., & Zhao, W. (2017) · New Journal of Chemistry · doi:10.1039/c7nj03279j · Cited by 11
Self-citationBornhütter, T., Ghogare, A. A., Preuß, A., et al. (2017) · Photochemistry and Photobiology · doi:10.1111/php.12773 · Cited by 4
Cited by
Sorted by citations
Emerging Applications of Chlorella sp. and Spirulina (Arthrospira) sp.
Abreu, A. P., Martins, R., & Nunes, J. (2023) · Bioengineering · doi:10.3390/bioengineering10080955 · Cited by 119
Metadata
- Authors
- Dong, Y., Li, G., Wang, L., Cao, L., Li, Y., & Zhao, W.
- Affiliations
- Dalian University of Technology (CN)
- Corresponding author
- Li, Guangzhe
- Zhao, Weijie
- Venue
- Journal of Photochemistry and Photobiology B: Biology
- Publisher
- Elsevier BV
- Published
- 2020-10
- Volume
- 211
- Pages
- 112015
- ISSN
- 1011-1344 (ISSN-L)
- OpenAlex
- W3083268711
- Cited by
- 20
- References
- 39
- Citations by year
- 2026: 4 · 2025: 3 · 2024: 3 · 2023: 5 · 2022: 1 · 2021: 4
- FWCI
- 1.41
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Photochemistry and Photobiology B Biology (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Key Projects of the National Science and Technology Pillar Program (2015BAD17B05)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Photodynamic Therapy Research Studies
- Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
- Physical Sciences › Engineering › Biomedical Engineering › Nanoplatforms for cancer theranostics
- Keywords
- chlorin e6, photosensitizers, photodynamic therapy, extended π-conjugation, singlet oxygen detection, HepG2 cells, H22 hepatocellular carcinoma, tumor accumulation, anticancer activity, dark cytotoxicity
- MeSH terms
- Animals, Antineoplastic Agents, Cell Survival, Humans, Hydrocarbons, Aromatic, Male, Mice, Inbred ICR, Photochemotherapy, Porphyrins, Structure-Activity Relationship, Photosensitizing Agents, Singlet Oxygen, Mice, Hep G2 Cells
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