Article
Chemistry, Applied
Feng Wang, Yinghua Gao, Jiahui Zhang, Laixing Wang, Leilei Bao, Yan Qiu, Hui Jin, Yijia Yan, Yiping Han, Feng Hong, Zhi-Long Chen
Summary: A series of chlorophyll derivatives with fluorine-substituted alkyl side chains were designed and synthesized, showing excellent photodynamic anti-tumor effects. Among them, compound F-C4-Ppa exhibited the most outstanding anti-tumor effect and is a promising candidate for photodynamic therapy and photo-imaging diagnosis.
Article
Chemistry, Applied
Feng Wang, Tao Xu, Gennady Meerovich, Zhi-Long Chen, Yi-Jia Yan
Summary: This article reports a method to improve the selectivity of photosensitizers to target pathological tissue by designing and synthesizing chlorophyll derivatives. These compounds showed intense absorption and fluorescence emission characteristics, as well as excellent singlet oxygen generation ability. One of the compounds, AZ-Ppa-2, demonstrated the ability to preferentially accumulate in cells overexpressing CAIX and showed outstanding photodynamic therapy anti-tumor effects.
Article
Chemistry, Multidisciplinary
Kuizhi Chen, Xia Li, Bingcheng Huang, Qiuhao Ye, Wenling Xiao, Xinqiao Guan, Limin Chen, Yiru Peng
Summary: Three new thienyl/benzothienyl/dibenzothienyl groups axially substituted silicon(iv) phthalocyanines were synthesized and characterized for their photophysical/photochemical properties. Among them, benzothienyl group substituted silicon(iv) phthalocyanine showed the highest fluorescence intensity, lifetime, and singlet oxygen quantum yield, and exhibited potential in mediating photodynamic therapy on MCF-7 breast cancer cells.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Fei Huang, Yu Li, Xing-Jie Zhang, Mei-Yu Lin, Gui-Yan Han, Hui-Ying Lin, Hui-Yun Lin, Zhenyuan Miao, Bu-Hong Li, Chun-Quan Sheng, Jian-Zhong Yao
Summary: Novel chlorin e6-based conjugate 10b, designed and synthesized as photosensitizer, showed strong phototoxicity against cancer cells by reducing efflux of intracellular photosensitizer and localizing in various organelles. It induced cell apoptosis, ROS production, autophagy, and cell cycle arrest. In vivo experiments demonstrated that 10b significantly inhibited tumor growth and prolonged survival time. Therefore, 10b has great potential as a promising photosensitizer.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Physical
Fei Huang, Guiyan Han, Xingjie Zhang, Yu Li, Zhenyuan Miao, Jianzhong Yao
Summary: In this study, a novel chlorin-based photosensitizer was designed and synthesized for tumor photodynamic therapy. The photosensitizer showed high phototoxicity, high dark toxicity/phototoxicity ratio, and excellent PDT antitumor efficacy in vitro and in vivo.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Pharmacology & Pharmacy
Til Bahadur Thapa Magar, Jusuk Lee, Ji Hoon Lee, Juhee Jeon, Pallavi Gurung, Junmo Lim, Yong-Wan Kim
Summary: A novel series of chlorin e6-curcumin derivatives were synthesized and tested for their photodynamic treatment (PDT) efficacy against human pancreatic cancer cell lines. Compound 17 showed excellent cellular internalization capability and higher phototoxicity compared to the parent compound Ce6. In pancreatic cell lines, 17 induced apoptosis in a dose-dependent manner and activated intrinsic apoptosis, resulting in cancer cell death. Structure-activity relationship studies revealed that the incorporation of additional methyl ester moiety and conjugation to the enone moiety of curcumin enhanced cellular uptake and PDT efficacy. In vivo PDT testing in melanoma mouse models demonstrated that 17-PDT greatly reduced tumor growth, indicating its potential as an effective photosensitizer for PDT anticancer therapy.
Article
Biochemistry & Molecular Biology
Rajeev Shrestha, Shyam Kumar Mallik, Junmo Lim, Pallavi Gurung, Til Bahadur Thapa Magar, Yong-Wan Kim
Summary: Photodynamic therapy (PDT) can eliminate cancer cells and induce antitumor immune response by using Chlorin e6 (Ce6). Two efficient synthetic methods for preparing Ce6 from Spirulina platensis were described, and the phototoxic effect of Ce6 was investigated in vitro and its antitumor activity in vivo. The results showed that Ce6-PDT not only suppressed tumor growth at the injection site but also induced antitumor immunity through upregulating the expression of IFN-gamma, TNF-alpha, and IL-2.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Atsushi Narumi, Rioko Rachi, Hiromi Yamazaki, Seigou Kawaguchi, Moriya Kikuchi, Hiroyuki Konno, Tomohiro Osaki, Yoshiharu Okamoto, Xiande Shen, Toyoji Kakuchi, Hiromi Kataoka, Akihiro Nomoto, Tomokazu Yoshimura, Shigenobu Yano
Summary: The study focuses on utilizing glucose-based oligosaccharide maltotriose (Mal(3)) to conjugate with chlorin e6 (Ce6), assisted by propargyl amine and tetraethylene glycol (TEG) derivative. The resulting Mal(3)-TEG-Ce6 conjugate shows desired photoabsorption properties in physiological media and exhibits high antitumor activity against canine mammary carcinoma (SNP) cells. In vitro tests on mouse mammary carcinoma (EMT6) cells reveal that Mal(3)-TEG-Ce6 induces apoptosis and necrosis through reactive oxygen species (ROS) generation.
Article
Biochemistry & Molecular Biology
Xiuhan Guo, Haoze Yu, Wanjie Shen, Rui Cai, Yueqing Li, Guangzhe Li, Weijie Zhao, Shisheng Wang
Summary: Researchers found that the PS-NO photosensitizers containing NO donors have stronger antitumor activity compared to chlorin e6, and can increase the levels of NO and ROS in cells. Additionally, the addition of the ferroptosis inhibitor Ferrostatin-1 significantly reduces the photodynamic activity of PS-NO and the levels of NO and ROS in cells.
BIOORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Rui Chang, Luyang Zhao, Ruirui Xing, Junbai Li, Xuehai Yan
Summary: This review summarizes recent advances in chromopeptide nanoarchitectonics, focusing on the design strategy, assembly mechanism, and structure-function relationship. The effect of peptide sequences and the variation in photophysical performance are critically emphasized. Various applications, including biomedicine and artificial photosynthesis, are discussed, along with the future prospects of chromopeptide nanoarchitectonics.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Materials Science, Multidisciplinary
Zi-jian Zhang, Zhong-tao Liu, Yun-peng Huang, William Nguyen, Yong-xiang Wang, Lihua Cheng, Hui Zhou, Yu Wen, Li Xiong, Wei Chen
Summary: A nanoparticle was designed with Fe3O4 as the core and BSA as the shell, releasing ferrous ions and CE6 in an acidic microenvironment. CE6 generates ROS to induce apoptosis under laser irradiation, while the ferrous ions catalyze the generation of excess ROS and lipid peroxides, inducing ferroptosis in colorectal cancer cells. Due to the synergistic effect of inducing apoptosis and ferroptosis, the imaging ability, and the good safety of each component, Fe3O4@BSA-CE6 nanoparticles are expected to be used in clinical applications in the future.
MATERIALS TODAY PHYSICS
(2023)
Article
Biochemistry & Molecular Biology
Chieh-Yu Chen, Ching-Yi Chen
Summary: A new fluorinated mixed micelle (M60@PFC-Ce6) is developed as a tumor-penetrating and oxygen-enriching nanoplatform, which shows great oxygen delivery capability, intracellular reactive oxygen species generation, and superior phototoxicity. It also has the ability to penetrate and accumulate within spheroids, providing a new nanoplatform for improving photodynamic therapy efficacy.
MACROMOLECULAR BIOSCIENCE
(2023)
Article
Engineering, Chemical
Til Bahadur Thapa Magar, Rajeev Shrestha, Pallavi Gurung, Junmo Lim, Yong-Wan Kim
Summary: This study demonstrated the preparation of the second-generation photosensitizer Chlorin e6 using a rapid and green synthetic method. Ce6 showed significant photodynamic cytotoxicity against melanoma cells and was used for photoacoustic imaging of internal organs in mice. Ce6-PDT holds promise as a strategy for cancer therapy and non-invasive visualization of internal organs.
Article
Chemistry, Applied
Bruna M. de Franca, Simone S. C. Oliveira, Lucieri O. P. Souza, Thais P. Mello, Andre L. S. Santos, Josue S. Bello Forero
Summary: The chelation of D-π-A-π-D curcumin dye with metals Cu (II) and Pd (II) was found to improve its photoactivity, showing antifungal and antileishmanial activities. The solvatochromism and acidochromism mechanisms were mainly influenced by the ICT system.
Article
Chemistry, Multidisciplinary
Mengliang Zhu, Hang Zhang, Guangliu Ran, Yuhang Yao, Zi-Shu Yang, Yingying Ning, Yi Yu, Ruijing Zhang, Xin-Xin Peng, Jiahui Wu, Zhifan Jiang, Wenkai Zhang, Bing-Wu Wang, Song Gao, Jun-Long Zhang
Summary: This paper reports on a next-generation photosensitizer that undergoes fast metabolism after treatment to reduce side effects, while still maintaining an effective therapeutic outcome and negligible phototoxic reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Tomoaki Tanase, Kanako Nakamae, Yume Okawa, Mami Hamada, Arimasa Matsumoto, Takayuki Nakajima, Takuya Nakashima, Tsuyoshi Kawai
Summary: A P-stereogenic linear tetraphosphine tetraoxide was synthesized to prepare lanthanide(III) complexes with P-chiral multidentate phosphine oxides. The photophysical properties of the complexes revealed significant chiral induction from the P-chiral centers through intramolecular pi-pi stacking constraint.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Yoshiyuki Nonoguchi, Tomoyuki Miyao, Chigusa Goto, Tsuyoshi Kawai, Kimito Funatsu
Summary: This study developed a method for dispersing SWCNTs in organic solvents using surfactants, achieving high dispersion efficiency. Feature extraction based on machine learning revealed important physicochemical factors that affect the dispersion, which are related to both surfactant and solvent-SWCNT interactions. The organic SWCNT dispersion method developed in this study may have wide applications in nanofluidics and functional materials design.
ADVANCED MATERIALS INTERFACES
(2022)
Article
Chemistry, Multidisciplinary
Takuya Nakashima, Riku Tanibe, Hiroto Yoshida, Masahiro Ehara, Miwa Kuzuhara, Tsuyoshi Kawai
Summary: Pathway-dependent chirality control in silver nanoclusters is achieved by using enantiomeric ligand, leading to the formation of chiral silver nanoclusters with intrinsic chirality. Guest binding to the nanoclusters' shell can reverse the stability between right- and left-handed nanoclusters, resulting in unprecedented chirality inversion.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Yasuto Nakagawa, Boda Yu, Yoshiaki Niidome, Keita Hayashi, Aleksandar Staykov, Miku Yamada, Takuya Nakashima, Tsuyoshi Kawai, Tsuyohiko Fujigaya, Tomohiro Shiraki
Summary: This study demonstrates that covalent attachment of a diarylethene derivative to single-walled carbon nanotubes introduces carbon defects, leading to near-infrared photoluminescence. Furthermore, reversible and repetitive wavelength switching of the photoluminescence is achieved based on photoisomerization of the diarylethene moieties on the nanotubes.
JOURNAL OF PHYSICAL CHEMISTRY C
(2022)
Article
Chemistry, Physical
Jumpei Kuno, Nicolas Ledos, Pierre-Antoine Bouit, Tsuyoshi Kawai, Muriel Hissler, Takuya Nakashima
Summary: This study demonstrates the induction of circularly polarized luminescence (CPL) in achiral fluorescent molecules by grafting them onto inorganic nanoparticles with a chiral shape. The chiralities of crystallography and morphology of mercury sulfide (HgS) nanoparticles are independently considered and the twist direction of the nanoparticles can be modified to regulate the sign of CPL signals. This research reveals a method for chirality control on inorganic nanoparticles.
CHEMISTRY OF MATERIALS
(2022)
Article
Chemistry, Organic
HaiYing Liu, Mikiya Suzuki, Kiyomi Kakiuchi, Tsuyoshi Kawai, Tsumoru Morimoto
Summary: This study reports a series of photolabile molecules based on 1,4-naphthoquinone (NQ), which can release various functional compounds under light irradiation. The synthesis of these compounds involves a concise method to attach different functional groups such as alcohols, amines, and acids. The functional compounds are masked with a common precursor and can be efficiently released through UV light irradiation.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Erin Hayashi, Naoto Akiyama, Kiyomi Kakiuchi, Tsuyoshi Kawai, Tsumoru Morimoto
Summary: We developed a rhodium(I)-catalyzed asymmetric cyclohydroformylation reaction of 1,6-enynes with formaldehyde. The reaction proceeds with high enantioselectivity, producing aldehyde products with higher-order structures. This method demonstrates wide compatibility and can be successfully applied to various enynes, providing a versatile route to access chiral aldehydes.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Colin J. Martin, Yora Goto, Ryosuke Asato, Gwenael Rapenne, Tsuyoshi Kawai
Summary: Four photochromic terarylenes with extended pi-conjugated thieno[b]thiophene units were synthesized. The position of the thieno[b]thiophene units determines the exclusion of photochromic ring-cyclization and cycloreversion behavior. A spontaneous fading reaction involving both thermal and cascade cycloreversion, depending on molecular structure, was observed. Electrochemical and computational studies were conducted to investigate the relative stability of the ground and cationic states in both isomers.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Materials Science, Multidisciplinary
Hayato Sakai, Yudai Suzuki, Makoto Tsurui, Yuichi Kitagawa, Takuya Nakashima, Tsuyoshi Kawai, Yuta Kondo, Go Matsuba, Yasuchika Hasegawa, Taku Hasobe
Summary: Chiral 1,1'-bi-2-naphthol (BINOL)-substituted boron dipyrromethene (BODIPY) derivatives with different numbers of phenyl groups were synthesized to study their aggregation-enhanced emission and circularly polarized luminescence (CPL). The self-assembly of 0Ph-B-BODIPY resulted in fibrous nanoarchitectures, while spherical nanoparticles were formed in 1Ph-B-BODIPY and 2Ph-B-BODIPY. The nanofibers of 0Ph-B-BODIPY exhibited broad emission and CPL spectra in the red to NIR regions, with enhanced dissymmetry factors compared to the monomer and 1Ph-B-BODIPY nanoparticles.
JOURNAL OF MATERIALS CHEMISTRY C
(2023)
Article
Materials Science, Multidisciplinary
Haru Hirai, Takuya Nakashima, Shinjiro Takano, Yukatsu Shichibu, Katsuaki Konishi, Tsuyoshi Kawai, Tatsuya Tsukuda
Summary: In this study, the effects of single-atom doping on the chiroptical properties of gold superatoms were investigated. It was found that single-atom doping can improve the chiroptical properties of gold superatoms, and this study provides a rational guide for enhancing their chiroptical activity.
JOURNAL OF MATERIALS CHEMISTRY C
(2023)
Article
Chemistry, Multidisciplinary
Marine Louis, Yan Bing Tan, Pablo Reine, Shohei Katao, Yoshiko Nishikawa, Fumio Asanoma, Tsuyoshi Kawai
Summary: This study reports on the crystal structures of three coordination polymers: [(Lambda,Lambda,Lambda,Lambda,Lambda,Lambda)- or/(Delta,Delta,Delta,Delta,Delta,Delta)Eu-6(III)(TTP)(8)(OH2)(6)Na-4]n with both conglomerate and racemic structures, (Delta,Delta,Delta,Delta)-/(Lambda,Lambda,Lambda,Lambda) Eu-4(III)(TTP)(4)(bipy)(4)(MEK)(2)(OH2)(2) with racemic tetrahedral clusters, and an achiral crystal structure of [Eu-2(III)(BTP)(4)(OH2)(2)Na-2]n (where BTP = dianionic bis-ss-diketonate, TTP = trianionic tris-ss-diketonate, and bipy = 2,2'-bipyridine). The TTP ligand's screw coordination arrangement leads to the formation of racemic EuIII products. The conglomerate crystallization of [EuIII6(TTP)8(OH2)6Na4]n is likely caused by the presence of sodium counterions and interactions between oxygen atoms and the trifluoromethyl unit of the TTP ligand and sodium ions. All Eu-III compounds exhibit characteristic red luminescence (5D0. 7FJ, J = 0-4) in solution or in the solid crystalline state. Circularly polarized luminescence (CPL) is observed in the chiral Eu-6(III)(TTP)(8)(OH2)(6)Na-4]n species, with a |glum| value ranging from 0.15 to 0.68 at the 5D0. 7F1 emission band. Subtle changes in the [Eu-6(III)(TTP)(8)(OH2)(6)Na-4]n structure, possibly due to twinned crystals or crystals that do not correspond to a perfect spontaneous resolution, account for the variation in observed CPL values.
Article
Chemistry, Multidisciplinary
Wataru Ishii, Yoshinori Okayasu, Yoichi Kobayashi, Rika Tanaka, Shohei Katao, Yoshiko Nishikawa, Takuya Nakashima, Tsuyoshi Kawai
Summary: The optical property of an ionic metal nanocluster (NC) is affected by the ionic interaction with counter ions. The modification of trianionic [Ag29(BDT)12(TPP)4]3- NC with silver(I) complexes led to intense photoluminescence (PL) in the near-infrared (NIR) region. The binding of silver(I) complexes to the peripheral region of Ag29 NC is confirmed by various measurements, and the change in excited-state dynamics by the binding is discussed.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Ruiji Li, Qi Fang, Minghui Chen, Mihoko Yamada, Yugo Tsuji, Yusuke Kugai, Wei Li, Tsuyoshi Kawai
Summary: This study reports the synthesis and photochemical characterization of diarylethene molecular switches based on diaryl[5]helicene. The compounds exhibit reversible photochromism and turn-off mode fluorescence photoswitching upon light irradiation. The photoinduced changes in aromaticity of the central ethene bridge facilitate the thermal bleaching rates of the switches. The research provides new insight for designing aromatic diarylethene photoswitches with reversible fluorescence switching and photoinduced changes in aromaticity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Materials Science, Multidisciplinary
Yugo Tsuji, Natsuko Kanno, Chigusa Goto, Shohei Katao, Yasuo Okajima, Pablo Reine, Paulius Imbrasas, Sebastian Reineke, Katsuyuki Shizu, Takuya Nakashima, Hironori Kaji, Tsuyoshi Kawai, Marine Louis
Summary: This work presents the synthesis and characterization of a carbazole-naphthalimide donor-acceptor pair for circularly polarized thermally activated delayed fluorescence. The monomeric form shows only fluorescence, while the dimeric form exhibits TADF emission. The dimerization greatly reduces the singlet-triplet energy gap, enabling TADF emission with high photoluminescence quantum yield. In addition, the chiral target shows high performance CPL at room and low temperature, and it undergoes a transition from yellow phase to orange/red phase under mechanical stress.
JOURNAL OF MATERIALS CHEMISTRY C
(2023)
Article
Materials Science, Multidisciplinary
Betsy Marydasan, Karthika Suryaletha, Amrutha Manoj Lena, Alida Sachin, Tsuyoshi Kawai, Sabu Thomas, Jatish Kumar
Summary: Nanomaterials with diverse properties have gained attention for their advantages in reducing material consumption and simplifying synthetic routes. This study reports the synthesis of optically active heterobimetallic EU(iii) complexes with promising luminescent and antibacterial properties, making them potential materials for bioimaging applications.
JOURNAL OF MATERIALS CHEMISTRY C
(2022)
