Chinese Journal of Lasers, Volume. 49, Issue 15, 1507101(2022)
Recent Advances in Two-Photon Excited Photodynamic Therapy
[1] Yun S H, Kwok S J J. Light in diagnosis, therapy and surgery[J]. Nature Biomedical Engineering, 1, 8(2017).
[2] Lucky S S, Soo K C, Zhang Y. Nanoparticles in photodynamic therapy[J]. Chemical Reviews, 115, 1990-2042(2015).
[3] Zhang C, Ren E, Pang X et al. Recent advances in nanophotosensitizers for antibacterial photodynamic therapy[J]. Chinese Journal of Lasers, 47, 0207012(2020).
[4] Li W B, Shen Y, Li B H. Advances in optical imaging for monitoring photodynamic therapy dosimetry[J]. Chinese Journal of Lasers, 47, 0207006(2020).
[5] Zhou Z J, Song J B, Nie L M et al. Reactive oxygen species generating systems meeting challenges of photodynamic cancer therapy[J]. Chemical Society Reviews, 45, 6597-6626(2016).
[6] Hu F, Xu S D, Liu B. Photosensitizers with aggregation-induced emission: materials and biomedical applications[J]. Advanced Materials, 30, e1801350(2018).
[7] Sun Z Y, Zhang L P, Wu F P et al. Photosensitizers for two-photon excited photodynamic therapy[J]. Advanced Functional Materials, 27, 1704079(2017).
[8] Qian C G, Yu J C, Chen Y L et al. Light-activated hypoxia-responsive nanocarriers for enhanced anticancer therapy[J]. Advanced Materials, 28, 3313-3320(2016).
[9] Du J J, Shi T C, Long S R et al. Enhanced photodynamic therapy for overcoming tumor hypoxia: from microenvironment regulation to photosensitizer innovation[J]. Coordination Chemistry Reviews, 427, 213604(2021).
[10] Berg K, Selbo P K, Weyergang A et al. Porphyrin-related photosensitizers for cancer imaging and therapeutic applications[J]. Journal of Microscopy, 218, 133-147(2005).
[11] Baskaran R, Lee J, Yang S G. Clinical development of photodynamic agents and therapeutic applications[J]. Biomaterials Research, 22, 25(2018).
[12] dos Santos A F, de Almeida D R Q, Terra L F et al. Photodynamic therapy in cancer treatment-an update review[J]. Journal of Cancer Metastasis and Treatment, 5, 25(2019).
[13] Tardivo J P, del Giglio A, de Oliveira C S et al. Methylene blue in photodynamic therapy: from basic mechanisms to clinical applications[J]. Photodiagnosis and Photodynamic Therapy, 2, 175-191(2005).
[14] Sheng Z H, Hu D H, Xue M M et al. Indocyanine green nanoparticles for theranostic applications[J]. Nano-Micro Letters, 5, 145-150(2013).
[15] Wang H L, Li X X, Tse B W C et al. Indocyanine green-incorporating nanoparticles for cancer theranostics[J]. Theranostics, 8, 1227-1242(2018).
[16] Bhandari C, Guirguis M, Savan N A et al. What NIR photodynamic activation offers molecular targeted nanomedicines: perspectives into the conundrum of tumor specificity and selectivity[J]. Nano Today, 36, 101052(2021).
[17] Brown S. Two photons are better than one[J]. Nature Photonics, 2, 394-395(2008).
[18] Helmchen F, Denk W. Deep tissue two-photon microscopy[J]. Nature Methods, 2, 932-940(2005).
[19] Zhang R L, Li H, Wu Y H et al. Identification of human coronary atherosclerotic plaques using spectrum- and time-resolved multiphoton microscopy[J]. Chinese Journal of Lasers, 47, 0207025(2020).
[20] Robbins E, Leroy-Lhez S, Villandier N et al. Prospects for more efficient multi-photon absorption photosensitizers exhibiting both reactive oxygen species generation and luminescence[J]. Molecules, 26, 6323(2021).
[21] Zhao J Z, Wu W H, Sun J F et al. Triplet photosensitizers: from molecular design to applications[J]. Chemical Society Reviews, 42, 5323-5351(2013).
[22] Pawlicki M, Collins H A, Denning R G et al. Two-photon absorption and the design of two-photon dyes[J]. Angewandte Chemie (International Ed. in English), 48, 3244-3266(2009).
[23] Nwaneshiudu A, Kuschal C, Sakamoto F H et al. Introduction to confocal microscopy[J]. The Journal of Investigative Dermatology, 132, e3(2012).
[24] Bolze F, Jenni S, Sour A et al. Molecular photosensitisers for two-photon photodynamic therapy[J]. Chemical Communications, 53, 12857-12877(2017).
[25] Hong G, Antaris A L, Dai H. Near-infrared fluorophores for biomedical imaging[J]. Nature Biomedical Engineering, 1, 10(2017).
[26] Lenz P. In vivo excitation of photosensitizers by infrared light[J]. Photochemistry and Photobiology, 62, 333-338(1995).
[27] Karotki A, Khurana M, Lepock J R et al. Simultaneous two-photon excitation of photofrin in relation to photodynamic therapy[J]. Photochemistry and Photobiology, 82, 443-452(2006).
[28] Secret E, Maynadier M, Gallud A et al. Two-photon excitation of porphyrin-functionalized porous silicon nanoparticles for photodynamic therapy[J]. Advanced Materials, 26, 7643-7648(2014).
[29] Beck T J, Burkanas M, Bagdonas S et al. Two-photon photodynamic therapy of C6 cells by means of 5-aminolevulinic acid induced protoporphyrin IX[J]. Journal of Photochemistry and Photobiology B, 87, 174-182(2007).
[30] Chen R, Huang Z F, Chen G N et al. Kinetics and subcellular localization of 5-ALA-induced PpIX in DHL cells via two-photon excitation fluorescence microscopy[J]. International Journal of Oncology, 32, 861-867(2008).
[31] Sengul O, Marazzi M, Monari A et al. Photophysical properties of novel two-photon absorbing dyes: assessing their possible use for singlet oxygen generation[J]. The Journal of Physical Chemistry C, 122, 16315-16324(2018).
[32] Wang J, Zhuo X L, Xiao X et al. AlPcS-loaded gold nanobipyramids with high two-photon efficiency for photodynamic therapy in vivo[J]. Nanoscale, 11, 3386-3395(2019).
[33] Shen Y Z, Shuhendler A J, Ye D J et al. Two-photon excitation nanoparticles for photodynamic therapy[J]. Chemical Society Reviews, 45, 6725-6741(2016).
[34] Huang Y, Qiu F, Chen R J et al. Fluorescence resonance energy transfer-based drug delivery systems for enhanced photodynamic therapy[J]. Journal of Materials Chemistry B, 8, 3772-3788(2020).
[35] Wang J, Zhang Z H, Zha S et al. Carbon nanodots featuring efficient FRET for two-photon photodynamic cancer therapy with a low fs laser power density[J]. Biomaterials, 35, 9372-9381(2014).
[36] Huang Y, Qiu F, Shen L Y et al. Combining two-photon-activated fluorescence resonance energy transfer and near-infrared photothermal effect of unimolecular micelles for enhanced photodynamic therapy[J]. ACS Nano, 10, 10489-10499(2016).
[37] Yang Y, Liu H L, Han M J et al. Multilayer microcapsules for FRET analysis and two-photon-activated photodynamic therapy[J]. Angewandte Chemie (International Ed. in English), 55, 13538-13543(2016).
[38] Cao H Q, Wang L, Yang Y et al. An assembled nano complex for improving both therapeutic efficiency and treatment depth in photodynamic therapy[J]. Angewandte Chemie (International Ed. in English), 57, 7759-7763(2018).
[39] Sun J H, Xin Q, Yang Y et al. Nitrogen-doped graphene quantum dots coupled with photosensitizers for one-/ two-photon activated photodynamic therapy based on a FRET mechanism[J]. Chemical Communications, 54, 715-718(2018).
[40] Abrahamse H, Hamblin M R. New photosensitizers for photodynamic therapy[J]. The Biochemical Journal, 473, 347-364(2016).
[41] McKenzie L K, Bryant H E, Weinstein J A. Transition metal complexes as photosensitisers in one- and two-photon photodynamic therapy[J]. Coordination Chemistry Reviews, 379, 2-29(2019).
[42] Gandioso A, Purkait K, Gasser G. Recent approaches towards the development of Ru(II) polypyridyl complexes for anticancer photodynamic therapy[J]. Chimia, 75, 845-855(2021).
[43] Zhang L P, Ding D. Recent advances of transition Ir(III) complexes as photosensitizers for improved photodynamic therapy[J]. VIEW, 2, 20200179(2021).
[44] Marian C M. Spin-orbit coupling and intersystem crossing in molecules[J]. Wiley Interdisciplinary Reviews: Computational Molecular Science, 2, 187-203(2012).
[45] Wainwright M. Non-porphyrin photosensitizers in biomedicine[J]. Chemical Society Reviews, 25, 351-359(1996).
[46] Kamkaew A, Lim S H, Lee H B et al. BODIPY dyes in photodynamic therapy[J]. Chemical Society Reviews, 42, 77-88(2013).
[47] Zhang X, Wang Z J, Hou Y Q et al. Recent development of heavy-atom-free triplet photosensitizers: molecular structure design, photophysics and application[J]. Journal of Materials Chemistry C, 9, 11944-11973(2021).
[48] Nguyen V N, Kumar A, Lee M H et al. Recent advances in biomedical applications of organic fluorescence materials with reduced singlet-triplet energy gaps[J]. Coordination Chemistry Reviews, 425, 213545(2020).
[49] Xu S D, Yuan Y Y, Cai X L et al. Tuning the singlet-triplet energy gap: a unique approach to efficient photosensitizers with aggregation-induced emission (AIE) characteristics[J]. Chemical Science, 6, 5824-5830(2015).
[50] Yang Z M, Zhang Z J, Sun Y Q et al. Incorporating spin-orbit coupling promoted functional group into an enhanced electron D-A system: a useful designing concept for fabricating efficient photosensitizer and imaging-guided photodynamic therapy[J]. Biomaterials, 275, 120934(2021).
[51] Nguyen V N, Qi S J, Kim S et al. An emerging molecular design approach to heavy-atom-free photosensitizers for enhanced photodynamic therapy under hypoxia[J]. Journal of the American Chemical Society, 141, 16243-16248(2019).
[52] Fowley C, Nomikou N, McHale A P et al. Extending the tissue penetration capability of conventional photosensitisers: a carbon quantum dot-protoporphyrin IX conjugate for use in two-photon excited photodynamic therapy[J]. Chemical Communications, 49, 8934-8936(2013).
[53] Zhao T T, Yu K, Li L et al. Gold nanorod enhanced two-photon excitation fluorescence of photosensitizers for two-photon imaging and photodynamic therapy[J]. ACS Applied Materials & Interfaces, 6, 2700-2708(2014).
[54] He G S, Tan L S, Zheng Q D et al. Multiphoton absorbing materials: molecular designs, characterizations, and applications[J]. Chemical Reviews, 108, 1245-1330(2008).
[55] Albota M, Beljonne D, Brédas J L et al. Design of organic molecules with large two-photon absorption cross sections[J]. Science, 281, 1653-1656(1998).
[56] Zhang Q, Tian X H, Zhou H P et al. Lighting the way to see inside two-photon absorption materials: structure-property relationship and biological imaging[J]. Materials, 10, 223(2017).
[57] Schafer K J, Belfield K D, Yao S et al. Fluorene-based fluorescent probes with high two-photon action cross-sections for biological multiphoton imaging applications[J]. Journal of Biomedical Optics, 10, 051402(2005).
[58] Andrade C D, Yanez C O, Rodriguez L et al. A series of fluorene-based two-photon absorbing molecules: synthesis, linear and nonlinear characterization, and bioimaging[J]. The Journal of Organic Chemistry, 75, 3975-3982(2010).
[59] Pond S J K, Rumi M, Levin M D et al. One- and two-photon spectroscopy of donor-acceptor-donor distyrylbenzene derivatives: effect of cyano substitution and distortion from planarity[J]. The Journal of Physical Chemistry A, 106, 11470-11480(2002).
[60] Xu L, Lin W J, Huang B B et al. The design strategies and applications for organic multi-branched two-photon absorption chromophores with novel cores and branches: a recent review[J]. Journal of Materials Chemistry C, 9, 1520-1536(2021).
[61] Wang H, Zhang Q, Zhang J et al. Synthesis, two-photon absorption properties and bioimaging applications of mono-,di- and hexa-branched pyrimidine derivatives[J]. Dyes and Pigments, 102, 263-272(2014).
[62] Nosaka Y, Nosaka A Y. Generation and detection of reactive oxygen species in photocatalysis[J]. Chemical Reviews, 117, 11302-11336(2017).
[63] Wu H Y, Song Q J, Ran G X et al. Recent developments in the detection of singlet oxygen with molecular spectroscopic methods[J]. TrAC Trends in Analytical Chemistry, 30, 133-141(2011).
[64] Entradas T, Waldron S, Volk M. The detection sensitivity of commonly used singlet oxygen probes in aqueous environments[J]. Journal of Photochemistry and Photobiology B, 204, 111787(2020).
[65] Wang S W, Wu W B, Manghnani P et al. Polymerization-enhanced two-photon photosensitization for precise photodynamic therapy[J]. ACS Nano, 13, 3095-3105(2019).
[66] Singh S, Aggarwal A, Bhupathiraju N V S D K et al. Glycosylated porphyrins, phthalocyanines, and other porphyrinoids for diagnostics and therapeutics[J]. Chemical Reviews, 115, 10261-10306(2015).
[67] Mei J, Leung N L C, Kwok R T K et al. Aggregation-induced emission: together we shine, united we soar![J]. Chemical Reviews, 115, 11718-11940(2015).
[68] Hu F, Huang Y Y, Zhang G X et al. Targeted bioimaging and photodynamic therapy of cancer cells with an activatable red fluorescent bioprobe[J]. Analytical Chemistry, 86, 7987-7995(2014).
[69] Yuan Y Y, Feng G X, Qin W et al. Targeted and image-guided photodynamic cancer therapy based on organic nanoparticles with aggregation-induced emission characteristics[J]. Chemical Communications, 50, 8757-8760(2014).
[70] Luo J, Xie Z, Lam J W et al. Aggregation-induced emission of 1-methyl-1, 2, 3, 4, 5-pentaphenylsilole[J]. Chemical Communications, 1740-1741(2001).
[71] Feng G X, Liu B. Aggregation-induced emission (AIE) dots: emerging theranostic nanolights[J]. Accounts of Chemical Research, 51, 1404-1414(2018).
[72] Dou Y D, Zhu Q, Du K. Recent advances in two-photon AIEgens and their application in biological systems[J]. Chembiochem: a European Journal of Chemical Biology, 22, 1871-1883(2021).
[73] Wang S W, Liu J, Goh C C et al. NIR-II-excited intravital two-photon microscopy distinguishes deep cerebral and tumor vasculatures with an ultrabright NIR-I AIE luminogen[J]. Advanced Materials, 31, e1904447(2019).
[74] Wang S W, Hu F, Pan Y T et al. Bright AIEgen-protein hybrid nanocomposite for deep and high-resolution in vivo two-photon brain imaging[J]. Advanced Functional Materials, 29, 1902717(2019).
[75] Wang Y, Han X, Xi W et al. Bright AIE nanoparticles with F127 encapsulation for deep-tissue three-photon intravital brain angiography[J]. Advanced Healthcare Materials, 6, 1700685(2017).
[76] Wang Y L, Chen M, Alifu N et al. Aggregation-induced emission luminogen with deep-red emission for through-skull three-photon fluorescence imaging of mouse[J]. ACS Nano, 11, 10452-10461(2017).
[77] Wang Y L, Hu R R, Xi W et al. Red emissive AIE nanodots with high two-photon absorption efficiency at 1040 nm for deep-tissue in vivo imaging[J]. Biomedical Optics Express, 6, 3783-3794(2015).
[78] Wang S W, Li X Q, Chong S Y et al. In vivo three-photon imaging of lipids using ultrabright fluorogens with aggregation-induced emission[J]. Advanced Materials, 33, e2007490(2021).
[79] Samanta S, Huang M N, Li S Q et al. AIE-active two-photon fluorescent nanoprobe with NIR-II light excitability for highly efficient deep brain vasculature imaging[J]. Theranostics, 11, 2137-2148(2021).
[80] Zheng Z, Zhang T F, Liu H X et al. Bright near-infrared aggregation-induced emission luminogens with strong two-photon absorption, excellent organelle specificity, and efficient photodynamic therapy potential[J]. ACS Nano, 12, 8145-8159(2018).
[81] Zhen S J, Wang S W, Li S W et al. Theranostics: efficient red/near-infrared fluorophores based on benzo[1, 2-b: 4, 5-b’] dithiophene 1, 1, 5, 5-tetraoxide for targeted photodynamic therapy and in vivo two-photon fluorescence bioimaging[J]. Advanced Functional Materials, 28, 1870087(2018).
[82] Qin W, Zhang P F, Li H et al. Ultrabright red AIEgens for two-photon vascular imaging with high resolution and deep penetration[J]. Chemical Science, 9, 2705-2710(2018).
[83] Qi J, Sun C W, Li D Y et al. Aggregation-induced emission luminogen with near-infrared-II excitation and near-infrared-I emission for ultradeep intravital two-photon microscopy[J]. ACS Nano, 12, 7936-7945(2018).
[84] Collins H A, Khurana M, Moriyama E H et al. Blood-vessel closure using photosensitizers engineered for two-photon excitation[J]. Nature Photonics, 2, 420-424(2008).
[85] Cao H Q, Yang Y, Qi Y F et al. Intraparticle FRET for enhanced efficiency of two-photon activated photodynamic therapy[J]. Advanced Healthcare Materials, 7, e1701357(2018).
[86] Gu B, Wu W, Xu G et al. Precise two-photon photodynamic therapy using an efficient photosensitizer with aggregation-induced emission characteristics[J]. Advanced Materials, 29, 1701076(2017).
[87] Shih A Y, Blinder P, Tsai P S et al. The smallest stroke: occlusion of one penetrating vessel leads to infarction and a cognitive deficit[J]. Nature Neuroscience, 16, 55-63(2013).
[88] Frederiksen P K, McIlroy S P, Nielsen C B et al. Two-photon photosensitized production of singlet oxygen in water[J]. Journal of the American Chemical Society, 127, 255-269(2005).
[89] Shen X Q, Li L, Chan A C M et al. Water-soluble conjugated polymers for simultaneous two-photon cell imaging and two-photon photodynamic therapy[J]. Advanced Optical Materials, 1, 92-99(2013).
[90] Wu W B, Bazan G C, Liu B. Conjugated-polymer-amplified sensing, imaging, and therapy[J]. Chem, 2, 760-790(2017).
[91] Wu W B, Mao D, Xu S D et al. Polymerization-enhanced photosensitization[J]. Chem, 4, 1937-1951(2018).
[92] Wang S W, Chen H, Liu J et al. NIR-II light activated photosensitizer with aggregation-induced emission for precise and efficient two-photon photodynamic cancer cell ablation[J]. Advanced Functional Materials, 30, 2002546(2020).
[93] Kenry , Duan Y, Liu B. Recent advances of optical imaging in the second near-infrared window[J]. Advanced Materials, 30, e1802394(2018).
[94] Zhu S J, Herraiz S, Yue J Y et al. 3D NIR-II molecular imaging distinguishes targeted organs with high-performance NIR-II bioconjugates[J]. Advanced Materials, 30, e1705799(2018).
[95] Wan H, Yue J, Zhu S et al. A bright organic NIR-II nanofluorophore for three-dimensional imaging into biological tissues[J]. Nature Communications, 9, 1171(2018).
[96] Horton N G, Wang K, Kobat D et al. In vivo three-photon microscopy of subcortical structures within an intact mouse brain[J]. Nature Photonics, 7, 205-209(2013).
[97] Kobat D, Horton N G, Xu C. In vivo two-photon microscopy to 1.6-mm depth in mouse cortex[J]. Journal of Biomedical Optics, 16, 106014(2011).
[98] Wang S W, Liu J, Feng G X et al. NIR-II excitable conjugated polymer dots with bright NIR-I emission for deep in vivo two-photon brain imaging through intact skull[J]. Advanced Functional Materials, 29, 1808365(2019).
[99] Dobos A, Steiger W, Theiner D et al. Screening of two-photon activated photodynamic therapy sensitizers using a 3D osteosarcoma model[J]. The Analyst, 144, 3056-3063(2019).
[100] Karges J, Kuang S, Maschietto F et al. Rationally designed ruthenium complexes for 1- and 2-photon photodynamic therapy[J]. Nature Communications, 11, 3262(2020).
[101] Zhou Z X, Liu J P, Rees T W et al. Heterometallic Ru-Pt metallacycle for two-photon photodynamic therapy[J]. Proceedings of the National Academy of Sciences of the United States of America, 115, 5664-5669(2018).
[102] Sun C L, Li J, Wang X Z et al. Rational design of organic probes for turn-on two-photon excited fluorescence imaging and photodynamic therapy[J]. Chem, 5, 600-616(2019).
[103] He X J, Bo S T, Gao M et al. Stereotactic photodynamic therapy using a two-photon AIE photosensitizer[J]. Small, 15, e1905080(2019).
Get Citation
Copy Citation Text
Shaowei Wang, Ming Lei. Recent Advances in Two-Photon Excited Photodynamic Therapy[J]. Chinese Journal of Lasers, 2022, 49(15): 1507101
Category: Optical Diagnostics and Therapy
Received: Dec. 7, 2021
Accepted: Feb. 11, 2022
Published Online: Jul. 29, 2022
The Author Email: Lei Ming (ming.lei@mail.xjtu.edu.cn)