{"title":"Halogenated BOIMPYs and Their Efficiency in Photodynamic Therapy","authors":"Worakrit Saiyasombat, Prapassara Muangsopa, Tunyawat Khrootkaew, Kantapat Chansaenpak, Piyanut Pinyou, Natakorn Sapermsap, Sorawis Sangtawesin, Anyanee Kamkaew","doi":"10.1002/cptc.202400109","DOIUrl":"10.1002/cptc.202400109","url":null,"abstract":"<p>BOIMPY (bis- (borondifluoride)-8-imidazodipyrromethene) photosensitizers were developed for imaging-guided photodynamic therapy (PDT). The introduction of heavy atoms (Br and I) to the <i>β</i>-positions of BOIMPY combined with the twisted structure of the molecule was the strategy to enhance the intersystem crossing process of the BOIMPYs and reduce intermolecular π–π interactions of BOIMPY core. To clarify the electronic features of BOIMPY derivatives, their optical properties were studied using UV-vis absorption, fluorescence spectroscopy, electrochemistry, and density functional theory (DFT) computing. The halogenated BOIMPYs exhibited a high absorption coefficient with high singlet oxygen generation ability (<i>Φ</i><sub>Δ</sub>=0.46 and 0.94 for brominated and iodinated BOIMPY, respectively). More significantly, an <i>in vitro</i> investigation showed that all derivatives displayed fluorescence in cancer cells and that the halogenated BOIMPYs increased the effectiveness of tumor inhibition upon exposure to 660 nm red LED light radiation. The half-maximal inhibitory concentrations for the iodinated and brominated BOIMPYs were 2.14 μM and 14.78 μM, respectively. Consequently, iodinated BOIMPY has been shown to represent a new class of photosensitizers with potential use in imaging-guided photodynamic therapy.</p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":"8 10","pages":""},"PeriodicalIF":3.0,"publicationDate":"2024-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140969453","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChemPhotoChemPub Date : 2024-05-16DOI: 10.1002/cptc.202400096
Zhenyan Zhou, Dr. Lei Wang, Shoucai Yan, Ziang Liu, Rensong Sun, Yuan Qiao, Prof. Dr. Engin U. Akkaya
{"title":"Reversing Reprogramming of Cancer Cell Metabolism by Singlet Oxygen Triggered Release of Dichloroacetate Enhances Photodynamic Cytotoxicity","authors":"Zhenyan Zhou, Dr. Lei Wang, Shoucai Yan, Ziang Liu, Rensong Sun, Yuan Qiao, Prof. Dr. Engin U. Akkaya","doi":"10.1002/cptc.202400096","DOIUrl":"10.1002/cptc.202400096","url":null,"abstract":"<p>Cancer cells change their glucose metabolism towards lactic acid production for various defensive and proliferative advantages. Dichloroacetate (DCA) is an inhibitor of a key enzyme and thus, changes back the OX-PHOS to glycolysis ratio. We designed and synthesized a singlet oxygen triggered source of dichloroacetate which releases this inhibitor during photodynamic singlet oxygen generation. Synergistic action of DCA and singlet oxygen results in significant enhancement of photocytotoxicity. The results suggest that this approach could offer significant improvement in the therapeutic outcome of PDT.</p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":"8 10","pages":""},"PeriodicalIF":3.0,"publicationDate":"2024-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140971790","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChemPhotoChemPub Date : 2024-05-13DOI: 10.1002/cptc.202400120
Dr. Lucas G. Furniel, Prof. Dr. Arlene G. Corrêa
{"title":"Photochemical Synthesis and Ring-Opening of Aziridines and Epoxides: State-of-the-Art","authors":"Dr. Lucas G. Furniel, Prof. Dr. Arlene G. Corrêa","doi":"10.1002/cptc.202400120","DOIUrl":"10.1002/cptc.202400120","url":null,"abstract":"<p>The development of greener methods for the preparation of three-membered rings has increased in the last decade, not only due to their biological activity but also to the ring strain of those heterocycles that make them useful precursors of more complex molecules. In this work, the visible-light-promoted synthesis and ring-opening of aziridines and epoxides, reported in the last five years, were reviewed. Both homogeneous and heterogeneous catalysts were discussed and, in addition, the plausible mechanism pathways were highlighted.</p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":"8 9","pages":""},"PeriodicalIF":3.0,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140942209","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChemPhotoChemPub Date : 2024-05-08DOI: 10.1002/cptc.202400128
Prof. Dr. Masaki Shimizu, Kenta Nishimura, Aoi Okusa, Dr. Tsuneaki Sakurai
{"title":"Front Cover: Efficient Solid-State Ultraviolet Emission of 2′,5′-Dioxy-p-terphenyls (ChemPhotoChem 5/2024)","authors":"Prof. Dr. Masaki Shimizu, Kenta Nishimura, Aoi Okusa, Dr. Tsuneaki Sakurai","doi":"10.1002/cptc.202400128","DOIUrl":"https://doi.org/10.1002/cptc.202400128","url":null,"abstract":"<p><b>The Front Cover</b> illustrates the molecular structure of 2′,5′-bis(triphenylsiloxy)-<i>p</i>-terphenyl in the center as a representative example of fluorophores that efficiently emit ultraviolet light in the solid state with emission maxima below 400 nm. Although UV light is invisible to the naked eye, the pale pink shadow of the molecular model is an expression of the efficient luminescence. Cover design by Shinji Muranaka. More information can be found in the Research Article by Masaki Shimizu and co-workers.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":"8 5","pages":""},"PeriodicalIF":3.7,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/cptc.202400128","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140880968","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChemPhotoChemPub Date : 2024-05-08DOI: 10.1002/cptc.202400132
Minqian Liu, Xiaoling Hou, Prof. Yawei Sun, Prof. Huajie Liu
{"title":"DNA Origami Steganography Based on Photocleavable Oligonucleotides","authors":"Minqian Liu, Xiaoling Hou, Prof. Yawei Sun, Prof. Huajie Liu","doi":"10.1002/cptc.202400132","DOIUrl":"10.1002/cptc.202400132","url":null,"abstract":"<p>DNA nanostructures have been regarded as promising platforms for molecular information coding for their high programmability and nanoscale addressability. However, steganography based on DNA nanostructures still needs further investigation. Here, we designed and synthesized a coumarin derivative structure with selective photo responsiveness in the visible light spectrum and developed a DNA origami steganography system that can only be decrypted through specific light exposure conditions. Under right light treatment, the effective cleavage of photoresponsive groups would cause some of the streptavidin binding sites to detach from the origami, thereby allowing the steganographic information to be read correctly.</p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":"8 10","pages":""},"PeriodicalIF":3.0,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140925970","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChemPhotoChemPub Date : 2024-05-07DOI: 10.1002/cptc.202400080
Farkas Domahidy, Beatrix Kovács, Dr. Levente Cseri, Dr. Gergely Katona, Dr. Balázs Rózsa, Dr. Zoltán Mucsi, Dr. Ervin Kovács
{"title":"Comprehensive Study of Thiazole-Orange-Based DNA Dyes","authors":"Farkas Domahidy, Beatrix Kovács, Dr. Levente Cseri, Dr. Gergely Katona, Dr. Balázs Rózsa, Dr. Zoltán Mucsi, Dr. Ervin Kovács","doi":"10.1002/cptc.202400080","DOIUrl":"10.1002/cptc.202400080","url":null,"abstract":"<p>The rapid advancement of biotechnology over the recent decades has amplified the importance of DNA detection and quantification assays. Many of these assays, such as gel electrophoresis, microscopy, flow cytometry, and the detection of amplification in quantitative polymerase chain reaction (qPCR), rely on the use of DNA-binding fluorescent dyes. This article presents a comprehensive study of six Thiazole-Orange-based fluorescent DNA-binding dyes: SYBR Safe, SYBR Green, Pico Green, SYTO-16, SYTO-9, and the benzothiazole-based analogue (TOPhBu) of the latter. The selected DNA markers were synthesized at a 10-milligram scale and characterised spectroscopically to quantify their fluorescence enhancement upon binding to double-stranded DNA. The ability of the dyes to detect DNA at low concentrations was evaluated using two new metrics, absolute fluorescence enhancement (AFE) and relative fluorescence enhancement (RFE). Quantum chemical calculations shed new light on the mechanism of their fluorogenicity through modelling the excited state behaviour and DNA binding of the dyes. Their analytical performance was further tested in qPCR experiments. The experimental results of this work highlight some important differences in the sensitivity and qPCR efficiency of the studied DNA-binding dyes which will facilitate the DNA marker selection for analytical purposes and the future development of novel DNA sensors.</p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":"8 10","pages":""},"PeriodicalIF":3.0,"publicationDate":"2024-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/cptc.202400080","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140925969","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChemPhotoChemPub Date : 2024-05-06DOI: 10.1002/cptc.202400081
Prof. Daichi Kitagawa, Yuya Seto, Misato Suganuma, Dr. Tatsumoto Nakahama, Prof. Hikaru Sotome, Prof. Syoji Ito, Prof. Hiroshi Miyasaka, Prof. Seiya Kobatake
{"title":"Emission Color Tuning of Inverse Type Diarylethene Crystals","authors":"Prof. Daichi Kitagawa, Yuya Seto, Misato Suganuma, Dr. Tatsumoto Nakahama, Prof. Hikaru Sotome, Prof. Syoji Ito, Prof. Hiroshi Miyasaka, Prof. Seiya Kobatake","doi":"10.1002/cptc.202400081","DOIUrl":"10.1002/cptc.202400081","url":null,"abstract":"<p>Organic luminescent solid materials have attracted much attention due to practical applications such as sensor materials and optical waveguides. We have previously reported that inverse type diarylethenes exhibit strong emission in crystal without causing aggregation-caused quenching. However, the emission color was limited to mainly green. To tune the emission color, in this work, we newly synthesized inverse type diarylethenes having a shortened π-conjugation length or a polar substituent and investigated their fluorescence properties in solutions and crystals. The crystals exhibited various emission colors from blue, green, yellow to red depending on the molecular structure. The emission color changes of the crystals were induced by the intermolecular interactions such as CH-π interactions in addition to the shortened π-conjugation length and the intramolecular charge transfer character.</p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":"8 9","pages":""},"PeriodicalIF":3.0,"publicationDate":"2024-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140887433","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChemPhotoChemPub Date : 2024-05-03DOI: 10.1002/cptc.202400107
Dr. Bin Zeng, Qin Zhou, Prof. Na Ta, Dr. Shengyang Wang, Prof. Can Li, Prof. Rengui Li
{"title":"Achieving Visible Light Triggered Overall Water Splitting over Plasmonic Au/SrTiO3:Al Photocatalyst","authors":"Dr. Bin Zeng, Qin Zhou, Prof. Na Ta, Dr. Shengyang Wang, Prof. Can Li, Prof. Rengui Li","doi":"10.1002/cptc.202400107","DOIUrl":"10.1002/cptc.202400107","url":null,"abstract":"<p>The surface plasmon resonance (SPR) effect has garnered extensive attention in semiconductor photocatalysis for solar energy conversion, thanks to its remarkable optical properties. However, the majority SPR-induced photocatalytic systems have been limited to achieving hydrogen evolution or oxygen evolution half reactions, and attaining overall water splitting on a SPR-induced photocatalyst under visible light remains a formidable challenging. In this study, we employed a plasmonic photocatalyst Au/SrTiO<sub>3</sub>, and further enhanced its performance by doping aluminum (Al) into the SrTiO<sub>3</sub> lattice (denoted as Au/SrTiO<sub>3</sub>:Al). By constructing reduction cocatalyst (RhCrO<sub>x</sub>) and oxidation cocatalyst (CoOOH), the Au/SrTiO<sub>3</sub>:Al photocatalyst successfully realizes photocatalytic overall water splitting with a stoichiometric ratio of H<sub>2</sub> and O<sub>2</sub> under visible light (λ≥440 nm). We revealed that the introduction of Al species effectively modified the electronic structure of SrTiO<sub>3</sub>, thereby enhancing the hydrogen evolution reaction in Au/SrTiO<sub>3</sub>:Al. Simultaneously, the RhCrO<sub>x</sub> and CoOOH cocatalysts synergistically capitalized on the short-lived hot electrons and holes generated by the plasmonic Au/SrTiO<sub>3</sub>:Al photocatalyst, enabling to realize photocatalytic overall water splitting. This work offers a promising avenue for the rational design of plasmon-induced overall water splitting photocatalysts through the integration of suitable cocatalysts and surface/interface engineering strategies.</p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":"8 9","pages":""},"PeriodicalIF":3.0,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140831596","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChemPhotoChemPub Date : 2024-05-03DOI: 10.1002/cptc.202400112
Dr. Damian E. Yerien, Prof. Sebastian Barata-Vallejo, Prof. Al Postigo
{"title":"Perfluoroalkylation Reactions by Electron Donor-Acceptor Complexes: Recent Advances","authors":"Dr. Damian E. Yerien, Prof. Sebastian Barata-Vallejo, Prof. Al Postigo","doi":"10.1002/cptc.202400112","DOIUrl":"10.1002/cptc.202400112","url":null,"abstract":"<p>This Perspective analyses the perfluoroalkylation reactions by electron donor-acceptor (EDA) complexes since 2018, while summarizes, in Tables 123, the vast majority of representative perfluoroalkylation reactions of various classes of organic compounds by EDA complexes and halogen-bonding interactions. Numerous intriguing reaction methodologies and valuable synthetic instances have emerged. We aim to delve into these new examples comprehensively, while also contemplating the future directions in the field. Subsequent sections will elaborate on the perfluoroalkylation of (hetero)aromatic compounds, carbon-carbon multiple bonds, perfluoroalkylation of carbonyl compounds, and perfluoroalkylation of isocyanides, covering their synthetic scope and mechanistic insights.\u0000</p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":"8 8","pages":""},"PeriodicalIF":3.0,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140831600","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
ChemPhotoChemPub Date : 2024-05-03DOI: 10.1002/cptc.202400005
Xun Zhang, Jingkun Wang, Yuliang Liu, Jidong Sun, Prof. Bingshe Xu, Prof. Tianbao Li
{"title":"Photoelectrocatalytic Reduction of CO2 to CO via Cu2O/C/PTFE Nanowires Photocathodes","authors":"Xun Zhang, Jingkun Wang, Yuliang Liu, Jidong Sun, Prof. Bingshe Xu, Prof. Tianbao Li","doi":"10.1002/cptc.202400005","DOIUrl":"10.1002/cptc.202400005","url":null,"abstract":"<p>The consumption of fossil fuels releases large amounts of carbon dioxide (CO<sub>2</sub>) in the atmosphere, causing a serious greenhouse effect. Photoelectrochemical (PEC) reduction of CO<sub>2</sub> to chemical fuels is an effective way to alleviate the current energy and environmental crisis. However, it is still difficult to rationally design efficient PEC CO<sub>2</sub> reduction photocathodes. Cuprous oxide (Cu<sub>2</sub>O) is a promising photocathode material, but its surface is susceptible to the accumulation of photogenerated electrons leading to corrosion and activity reduction, and is accompanied by hydrogen evolution reaction (HER), both of which lead to the overall low conversion efficiency of CO<sub>2</sub> reduction by Cu<sub>2</sub>O. In this study, the PEC CO<sub>2</sub> conversion efficiency was improved by the synergistic effect of the C electron transport layer to accelerate the electron transfer to alleviate the Cu<sub>2</sub>O corrosion problem and the polytetrafluoroethylene (PTFE) hydrophobic layer to inhibit the HER. The test showed that the CO yield of Cu<sub>2</sub>O/C/PTFE at the optimum potential (−0.7 V vs. RHE) was 54.6 μmol cm<sup>−2</sup> h<sup>−1</sup>, which was 3.2 times higher than that of pure Cu<sub>2</sub>O. This study provides a facile strategy for constructing an efficient photocathode with great potential for CO<sub>2</sub> reduction.</p>","PeriodicalId":10108,"journal":{"name":"ChemPhotoChem","volume":"8 10","pages":""},"PeriodicalIF":3.0,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140831970","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}