Enhancing the Stability and Photothermal Conversion Efficiency of ICG by Pillar[5]arene-Based Host-Guest Interaction

Yue Ding1, Chenwei Wang1, Bing Lü1, Yong Yao1
1School of Chemistry and Chemical Engineering, Nantong University, Nantong, China

Tóm tắt

Indocyanine green (ICG) is a classical near-infrared (NIR) photothermal reagent that can be employed in clinical medical detection. Under neutral conditions, ICG can adsorb NIR light effectively for photothermal (PTT) and photodynamic (PDT) therapy. However, ICG is easily degraded in weak acid environments, which seriously restricts its application. In this work, a cationic water-soluble pillar[5]arene (WP5) was selected as the stabilizing agent for ICG. Thanks to the host-guest interaction between WP5 and alkyl sulfonate, the stability and the photothermal conversion efficiency of ICG increased remarkably upon addition of WP5 as investigated by UV-vis spectrum and photothermal studies. Furthermore, an in vitro study showed higher efficiency of WP5&ICG in killing cancer cells in a shorter treatment time than the free ICG. Hence, it is hopeful that WP5 can be a new type of supramolecular host in enhancing the stability and photothermal conversion efficiency of photosensitizers.

Từ khóa


Tài liệu tham khảo

Cai, 2021, Recent Development of Pillar[n]arene-Based Amphiphiles, Chin. Chem. Lett., 32, 1267, 10.1016/j.cclet.2020.10.036

Cao, 2021, Pillararene-based Self-Assemblies for Electrochemical Biosensors, Biosens. Bioelectron., 181, 113164, 10.1016/j.bios.2021.113164

Cen, 2020, Cationic Water-Soluble Pillar[5]arene-Modified Cu2-xSe Nanoparticles: Supramolecular Trap for ATP and Application in Targeted Photothermal Therapy in the NIR-II Window, ACS Macro Lett., 9, 1558, 10.1021/acsmacrolett.0c00714

Chao, 2020, A Supramolecular Nanoprodrug Based on a Boronate Ester Linked Curcumin Complexing with Water-Soluble Pillar[5]arene for Synergistic Chemotherapies, Chem. Commun., 56, 8861, 10.1039/D0CC04315J

Chen, 2021, Synergistic Enhancement of the Emergency Treatment Effect of Organophosphate Poisoning by a Supramolecular Strategy, Chem. Sci., 12, 5202, 10.1039/D1SC00426C

Chen, 2013, Chiral Selective Transmembrane Transport of Amino Acids through Artificial Channels, J. Am. Chem. Soc., 135, 2152, 10.1021/ja312704e

Chernikova, 2020, Cucurbiturils in Nucleic Acids Research, Chem. Commun., 56, 15360, 10.1039/D0CC06583H

Dong, 2014, A Pillar[5]arene/imidazolium [2]rotaxane: Solvent- and Thermo-Driven Molecular Motions and Supramolecular Gel Formation, Chem. Sci., 5, 247, 10.1039/C3SC52481G

Duan, 2020, Facile One-step Electrodeposition Preparation of Cationic Pillar[6]arene-Modified Graphene Films on Glassy Carbon Electrodes for Enhanced Electrochemical Performance, Front. Chem., 8, 430, 10.3389/fchem.2020.00430

Guo, , Pillar[5]arene-based Supramolecular Assemblies with Two-step Sequential Fluorescence Enhancement for Mitochondria-Targeted Cell Imaging, J. Mater. Chem. C, 8, 15622, 10.1039/D0TC04343E

Guo, , Pillar[5]arene-Based [2]Rotaxane: Synthesis, Characterization, and Application in a Coupling Reaction, Inorg. Chem., 59, 11915, 10.1021/acs.inorgchem.0c01752

Han, 2020, Synthesis and Characterization of Bis-[1]rotaxanes via Salen-Bridged Bis-Pillar[5]arenes, Chin. Chem. LettersChem. Lett., 31, 725, 10.1016/j.cclet.2019.09.014

Hao, 2020, A Supramolecular Artificial Light‐Harvesting System with Two‐Step Sequential Energy Transfer for Photochemical Catalysis, Angew. Chem. Int. Ed., 59, 10095, 10.1002/anie.201912654

Issels, 2008, Hyperthermia Adds to Chemotherapy, Eur. J. Cancer, 44, 2546, 10.1016/j.ejca.2008.07.038

Jiang, 2020, Cucurbiturils Brighten Au Nanoclusters in Water, Chem. Sci., 11, 3531, 10.1039/D0SC00473A

Jie, 2020, Mechanochemical Synthesis of Pillar[5]quinone Derived Multi-Microporous Organic Polymers for Radioactive Organic Iodide Capture and Storage, Nat. Commun., 11, 1086, 10.1038/s41467-020-14892-y

Lai, 2017, Chemistry and Engineering of Cyclodextrins for Molecular Imaging, Chem. Soc. Rev., 46, 6379, 10.1039/C7CS00040E

Li, 2020, Resorcinarene Induced Assembly of Carotene and Lutein into Hierarchical Superstructures, J. Am. Chem. Soc., 142, 20583, 10.1021/jacs.0c10901

Liu, 2019, Photothermal Therapy and Photoacoustic Imaging via Nanotheranostics in Fighting Cancer, Chem. Soc. Rev., 48, 2053, 10.1039/C8CS00618K

Mcguire, 2016, World Cancer Report 2014. Geneva, Switzerland: World Health Organization, International Agency for Research on Cancer, WHO Press, 2015, Adv. Nutr., 7, 418, 10.3945/an.116.012211

Ogoshi, 2019, Applications of Pillar[ N ]arene‐Based Supramolecular Assemblies, Angew. Chem. Int. Ed., 58, 2197, 10.1002/anie.201805884

Ogoshi, 2008, para-Bridged Symmetrical Pillar[5]arenes: Their Lewis Acid Catalyzed Synthesis and Host-Guest Property, J. Am. Chem. Soc., 130, 5022, 10.1021/ja711260m

Shafirstein, 2012, Indocyanine green Enhanced Near-Infrared Laser Treatment of Murine Mammary Carcinoma, Int. J. Cancer, 130, 1208, 10.1002/ijc.26126

Shangguan, 2017, Enhancing the Solubility and Bioactivity of Anticancer Drug Tamoxifen by Water-Soluble Pillar[6]arene-Based Host-Guest Complexation, Chem. Commun., 53, 9749, 10.1039/C7CC05305C

Sheng, 2020, Separation of 2-Chloropyridine/3-Chloropyridine by Nonporous Adaptive Crystals of Pillararenes with Different Substituents and Cavity Sizes, J. Am. Chem. Soc., 142, 6360, 10.1021/jacs.0c01274

Sheng, 2013, Indocyanine Green Nanoparticles for Theranostic Applications, Nano-micro Lett., 5, 145, 10.1007/bf03353743

Shin, 2021, Pillar[5]-bis-trithiacrown: Influence of Host-Guest Interactions on the Formation of Coordination Networks, Inorg. Chem., 60, 5804, 10.1021/acs.inorgchem.1c00114

Song, 2021, Pillar[5]arene‐Modified Gold Nanorods as Nanocarriers for Multi‐Modal Imaging‐Guided Synergistic Photodynamic‐Photothermal Therapy, Adv. Funct. Mater., 31, 2009924, 10.1002/adfm.202009924

Song, 2015, Recent Advances in the Development of Organic Photothermal Nano-Agents, Nano Res., 8, 340, 10.1007/s12274-014-0620-y

Strilets, 2020, Biomimetic Approach for Highly Selective Artificial Water Channels Based on Tubular Pillar[5]arene Dimers, Angew. Chem. Int. Ed., 59, 23213, 10.1002/anie.202009219

Wan, 2020, Oxacalix[4]arene-bridged Pillar[5]arene Dimers: Syntheses, Planar Chirality and Construction of Chiral Rotaxanes, Chem. Commun., 56, 10155, 10.1039/D0CC04375C

Xiao, 2019, Stimuli-responsive Nanocarriers Constructed from Pillar[n]arene-Based Supra-amphiphiles, Mater. Chem. Front., 3, 1973, 10.1039/C9QM00428A

Xiao, 2018, Advanced Functional Materials Constructed from Pillar[n]arenes, Isr. J. Chem., 58, 1219, 10.1002/ijch.201800026

Xu, 2020, Structural Diversification of Pillar[ N ]arene Macrocycles, Angew. Chem. Int. Ed., 59, 6314, 10.1002/anie.202002467

Xue, 2012, Pillararenes, A New Class of Macrocycles for Supramolecular Chemistry, Acc. Chem. Res., 45, 1294, 10.1021/ar2003418

Yao, 2017, A Pillar[5]arene Based Gel from a Low-Molecular-Weight Gelator for Sustained Dye Release in Water, Dalton Trans., 46, 16802, 10.1039/C7DT04001F

Yao, 2016, Improved In Vivo Tumor Therapy via Host-Guest Complexation, J. Mater. Chem. B, 4, 2691, 10.1039/C5TB02611C

Yoo, 2019, Cation-controlled Catalysis with crown Ether-Containing Transition Metal Complexes, Chem. Commun., 55, 5047, 10.1039/C9CC00803A

Zhang, 2020, Supramolecular Polymer Networks Based on Pillar[5]arene: Synthesis, Characterization and Application in the Fenton Reaction, Chem. Commun., 56, 948, 10.1039/C9CC09155F

Zheng, 2021, The Recent Progress on Metal-Organic Frameworks for Phototherapy, Chem. Soc. Rev., 50, 5086, 10.1039/D1CS00056J

Zhou, 2017, Reversible Photo-Gated Transmembrane Channel Assembled from an Acylhydrazone-Containing crown Ether Triad, Chem. Commun., 53, 3681, 10.1039/C7CC01123G