Article
Chemistry, Multidisciplinary
Kun-Xu Teng, Wen-Kai Chen, Li-Ya Niu, Wei-Hai Fang, Ganglong Cui, Qing-Zheng Yang
Summary: Developing Type-I photosensitizers that can generate superoxide radicals under light irradiation has been shown to be an effective approach for improving photodynamic therapy for hypoxic tumors. The reported alpha,beta-linked BODIPY dimers and trimer exclusively generate superoxide radicals through an efficient excited-state relaxation process, demonstrating superior performance in PDT under hypoxic conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Lukas Schneider, Martina Kalt, Samuel Koch, Shanmugi Sithamparanathan, Veronika Villiger, Johann Mattiat, Flavia Kradolfer, Ekaterina Slyshkina, Sandra Luber, Mathias Bonmarin, Caroline Maake, Bernhard Spingler
Summary: This article reports six novel and easily accessible BODIPY-based agents for cancer treatment that exhibit both photodynamic and photothermal activities, and do not rely on the generation of reactive oxygen species for cytotoxicity. These agents demonstrate high photocytotoxicity and low dark toxicity in different cancer cell lines. Under hypoxic conditions, they exhibit oxygen-independent photothermal mechanisms, making them potential candidates for overcoming limitations in current cancer therapy.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Medicinal
Elif Yildiz Gul, Elanur Aydin Karatas, Hatice Aydin Dogan, Omer Faruk Karatas, Buenyemin Cosut, Esra Tanriverdi Ecik
Summary: In this study, smart photosensitizers containing BODIPY, erlotinib, and hydrophilic units were prepared and their physicochemical properties and PDT effects were investigated. The halogenated derivatives showed lower fluorescence and good ROS generation ability under red light. In vitro experiments demonstrated the potent activity of the halogenated conjugates on cancer cell viability and their low dark toxicity.
Article
Chemistry, Multidisciplinary
Mrunesh Koli, Sonali Gupta, Saikat Chakraborty, Ayan Ghosh, Rajib Ghosh, A. P. Wadawale, Tapan K. Ghanty, Birija S. Patro, Soumyaditya Mula
Summary: Fused compounds containing BODIPY and hetero[5]helicene structures were designed and synthesized, which showed superior optical properties and high intersystem crossing (ISC) efficiency. The increase in twisting angles and the replacement of certain units enhanced the triplet conversion and absorption performance. These compounds exhibited efficient cancer cell killing and have potential as heavy-atom-free photosensitizers for photodynamic therapy.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Engineering, Biomedical
Jigai li, Xianfa Du, Xin Zhou, Juyoung Yoon
Summary: A simple and effective approach is developed to create heavy-atom-free photosensitizers (PSs) for photodynamic therapy (PDT) by self-assembling long-tailed boron dipyrromethene dyes (BODIPYs). The resulting PSs can efficiently convert their excited energy to the triplet state, producing reactive oxygen species that are essential for PDT. The aggregation and PDT performance of the PSs can be regulated by adjusting the length of the tailed alkyl chains. Efficacy of these heavy-atom-free PSs is demonstrated in vitro and in vivo under both normoxic and hypoxic conditions.
ADVANCED HEALTHCARE MATERIALS
(2023)
Article
Biochemistry & Molecular Biology
Fen Qi, Hao Yuan, Yuncong Chen, Yan Guo, Shuren Zhang, Zhipeng Liu, Weijiang He, Zijian Guo
Summary: This study designed and synthesized two BODIPY-based monofunctional Pt (II) complexes and studied their PDT effects. The results showed that the complexes exhibited specific phototoxicity to cancer cells under irradiation.
JOURNAL OF INORGANIC BIOCHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Orlando Santoro, Miryam Chiara Malacarne, Francesco Sarcone, Luca Scapinello, Stefania Pragliola, Enrico Caruso, Viviana Teresa Orlandi, Lorella Izzo
Summary: In this study, two compounds from the BODIPY family were bound to amino-pendant groups of three random copolymers with varying amounts of MMA and DMAEMA. The copolymers showed inherent bactericidal activity due to the presence of amino groups and quaternized nitrogens bound to BODIPY. Coated filter paper discs with copolymers conjugated to BODIPY inhibited the growth of E. coli and S. aureus under green light irradiation, with the highest efficiency observed in the copolymer containing 43% DMAEMA and approximately 0.70 wt/wt% BODIPY. The copolymers also exhibited residual antimicrobial activity after dark incubation.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Qingbao Gong, Kai Cheng, Qinghua Wu, Wanwan Li, Changjiang Yu, Lijuan Jiao, Erhong Hao
Summary: A Cu(I)-promoted oxidative dimerization method was developed to synthesize a series of alpha,alpha- ethylene-bridged BODIPY dimers and trimers with high fluorescence intensity, small line widths, and intense fluorescence. This methodology relies on a singlet-electron-transfer process between alkylated BODIPYs and Cu(I) salt to generate BODIPY-based radical species, resulting in selective radical homocoupling reactions without harsh conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Thanh Chung Pham, Moonyeon Cho, Van-Nghia Nguyen, Thuy Kieu Van Nguyen, Gyoungmi Kim, Suhong Min, Mi-Ra Kim, Juyoung Yoon, Songyi Lee
Summary: In this study, heavy-atom-free photosensitizer molecules were designed and the correlation between ISC rate and 1O2 generation was investigated. Among the designed structures, Cbz-SB showed the best performance in terms of fluorescence emission and 1O2 generation, demonstrating its potential applicability in mitochondria-targeted fluorescence bioimaging and PDT of HeLa cells.
Article
Chemistry, Applied
Busra Arslan, Kubra Bilici, Gozde Demirci, Toghrul Almammadov, Minahil Khan, Alphan Sennaroglu, Havva Yagci Acar, Safacan Kolemen
Summary: Activity based photosensitizers are gaining attention for their selective action on cancer cells under light irradiation. A novel activatable PDT agent HCL was reported, selectively activated by the LAP enzyme in cancer cells with high LAP levels, showing effective photocytotoxicity with minimal dark toxicity. HCL could serve as an effective and tumor-associated LAP-sensitive phototheranostic agent.
Article
Chemistry, Physical
Rachel K. Swedin, Andrew T. Healy, Jacob W. Schaffner, Ilya A. Kuzmin, Yuriy V. Zatsikha, Victor N. Nemykin, David A. Blank
Summary: The excited state dynamics in two fully characterized pyridoneBODIPY-fullerene complexes were investigated. Efficient energy transfer and internal conversion were observed in the presence of the fullerene, allowing the excited state energy to be transferred back to the pyridoneBODIPY chromophore. The attachment chemistry of the fullerene affected the triplet-triplet energy transfer and the relaxation rate of the final triplet state.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
Alejandro Prieto-Castaneda, Fernando Garcia-Garrido, Carolina Diaz-Norambuena, Blanca Escriche-Navarro, Alba Garcia-Fernandez, Jorge Banuclos, Esther Rebollar, Inmaculada Garcia-Moreno, Ramon Martinez-Manez, Santiago de la Moya, Antonia R. . Agarrabeitia, Maria J. Ortiz
Summary: We have established an easy synthetic protocol for selectively developing all-orthogonal BODIPY trimers with unprecedented geometries. The trimer has been shown to serve as a molecular platform for the development of new, advanced heavy-atom-free photosensitizers for photodynamic therapy and phototheragnosis.
Article
Biochemistry & Molecular Biology
Diego Navarro-Barreda, Rosa de Llanos, Juan F. Miravet, Francisco Galindo
Summary: Two new brominated BODIPYs containing amino acid-based chains were synthesized and characterized. These compounds showed efficient generation of singlet oxygen in organic solvents but not in aqueous media. However, both compounds exhibited positive antimicrobial activity against gram-positive and gram-negative bacteria. The higher efficiency of compound 2 can be attributed to the presence of a protonatable residue, allowing more effective interaction with the cell walls of microorganisms.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY
(2022)
Review
Immunology
Xiaoyun Wang, Lian Wang, Reza Fekrazad, Lu Zhang, Xian Jiang, Gu He, Xiang Wen
Summary: This comprehensive review discusses the use of polyphenolic natural products as photosensitizers (PSs) in antimicrobial photodynamic therapy (aPDT). Polyphenolic natural products have unique chemical structures and antimicrobial properties, and are abundant and safe for human use. The review elaborates on various important polyphenolic compounds, their characteristics, properties, and antimicrobial effects, and also discusses the mechanisms of aPDT.
FRONTIERS IN IMMUNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Jongjit Treekoon, Kantapat Chansaenpak, Gamolwan Tumcharern, Zurain Syahira Zaiman Zain, Hong Boon Lee, Chin Siang Kue, Anyanee Kamkaew
Summary: Polymeric nanoparticles loaded with aza-BODIPY were successfully prepared for targeted nanodelivery, exhibiting monodisperse spherical morphology. These nanoparticles showed significant therapeutic effects on breast cancer cells and demonstrated tumor growth inhibition in vivo.
MATERIALS CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Serdal Kaya, Yahya A. Ismaiel, Nahyun Kwon, Gyoungmi Kim, Jose L. Bila, Juyoung Yoon, Ozlem Seven, Engin U. Akkaya
Summary: Singlet oxygen is a cytotoxic reactive species involved in cancer photodynamic therapy. Bodipy-based fluorescent dyes with singlet oxygen reactive modules can signal the intracellular generation of singlet oxygen through photosensitization. Long wavelength probes of singlet oxygen based on this approach are expected to be highly valuable.
Review
Chemistry, Inorganic & Nuclear
Hande Gunduz, Safacan Kolemen, Engin U. Akkaya
Summary: The detection and imaging of singlet oxygen is a challenging task due to its short half-life and solvent sensitivity. Selective probes for singlet oxygen are crucial in the presence of other oxidizing species, and smart designs are already making progress in pushing signalling events towards longer wavelengths of the visible spectrum.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Lei Wang, Lei Tang, Yingjie Liu, Hao Wu, Ziang Liu, Jin Li, Yue Pan, Engin U. Akkaya
Summary: This study demonstrates a method to release singlet oxygen through thermal endoperoxide cycloreversion and deliver it selectively to specific cancer cells, providing an effective and targeted therapeutic option. Unlike typical photodynamic processes, this method does not rely on light or oxygen, making it potentially applicable for deep-seated tumors.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Hao Wu, Ziang Liu, Yujie Shao, Guangzhe Li, Yue Pan, Lei Wang, Engin U. Akkaya
Summary: A newly discovered compound shows potential in inhibiting and reversing the pathogenesis of Alzheimer's disease. It releases singlet oxygen, reducing the cytotoxicity of amyloid-beta aggregates, and has good blood-brain barrier permeability.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Deniz Yildiz, Serdal Kaya, Abdurrahman Turksoy, Engin U. Akkaya
Summary: In this study, a novel approach for generating singlet oxygen on nanoparticles was presented. The modified nanoparticles can serve as a source of singlet oxygen through photosensitization or by thermal cycloreversion reaction. The nanoparticle-based agent can be easily recovered and reused, allowing for the availability of singlet oxygen in a convenient manner and broadening its scope of reactions.
MOLECULAR SYSTEMS DESIGN & ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Ziang Liu, Hao Wu, Jin Li, Lei Wang, Engin U. Akkaya
Summary: Naphthalene endoperoxides can undergo thermal cycloreversion reactions to produce singlet oxygen, and this reaction rate depends on structural features. By synthesizing a dimeric endoperoxide, it is possible to maintain singlet oxygen release rates within a selected range for a longer period of time.
Article
Chemistry, Multidisciplinary
Jin Li, Lei Wang, Jinrong Li, Yujie Shao, Ziang Liu, Guangzhe Li, Engin U. Akkaya
Summary: Naphthalene endoperoxides are convenient sources of singlet oxygen but their potential as ground-state molecular oxygen carriers remains largely unexplored. A compound with a bimodular design, incorporating an endoperoxide and a physical quencher of singlet oxygen, produces exclusively ground-state molecular oxygen. This compound shows potential as a highly tunable and targetable oxygen carrier in cell culture experiments, enhancing and sustaining cell proliferation.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Hao Wu, Lei Wang, Yang Wang, Yujie Shao, Guangzhe Li, Kun Shao, Engin U. Akkaya
Summary: By utilizing a dual-module design with a hypoxia responsive unit and fluoride-triggered endoperoxide unit, we have established a bioorthogonal metabolic shunt that enables controlled generation of singlet oxygen in cells, resulting in significantly different cytotoxicity under hypoxic and normoxic conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Nanoscience & Nanotechnology
Shengli Zhang, Peng Liu, Li Li, Ziang Liu, Xiao Qian, Xueying Jiang, Wen Sun, Lei Wang, Engin U. U. Akkaya
Summary: A near-infrared light-driven photoaffinity labeling approach using upconverting nanoparticle-based photoactive probes is developed for efficient and selective protein labeling. The labeled proteins can be easily isolated and purified, and the method demonstrates good tissue penetrating capacity for in vivo protein labeling.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Multidisciplinary
Min Qu, Nan Wu, Wanqing Jiang, Lei Wang, Mahinur S. Akkaya, Engin U. Akkaya
Summary: Singlet oxygen is a cytotoxic agent with short half-life that can be generated by chemical or photochemical methods; by releasing it in a stable structure, its antibacterial action can be utilized at specific locations. The rapid release of singlet oxygen with added fluoride ions enhances its bactericidal action, providing a potentially exciting alternative for combating antibiotic resistant bacterial strains.
Article
Chemistry, Multidisciplinary
Meina Liu, Esma Ucar, Ziang Liu, Lei Wang, Li Yang, Jiawei Xu, Engin U. Akkaya
Summary: Singlet oxygen generated by photosensitization has limited potential in vivo due to light attenuation in tissues, but controlled chemical generation of this reactive oxygen species may open up new therapeutic opportunities. The novel 1,4-naphthalene endoperoxides proposed as potential anti-coagulant agents due to thermal release of singlet oxygen offer advantages in terms of activity limitation and potential reduction of off-target anticoagulant side effects.
Article
Chemistry, Multidisciplinary
Seylan Ayan, Gurcan Gunaydin, Nisa Yesilgul-Mehmetcik, M. Emre Gedik, Ozlem Seven, Engin U. Akkaya
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Abdurrahman Turksoy, Deniz Yildiz, Simay Aydonat, Tutku Beduk, Merve Canyurt, Bilge Baytekin, Engin U. Akkaya
Article
Chemistry, Multidisciplinary
Esma Ucar, Dongmei Xi, Ozlem Seven, Cansu Kaya, Xiaojun Peng, Wen Sun, Engin U. Akkaya
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Physical
Esma Ucar, Ozlem Seyen, Dayoung Lee, Gyoungmi Kim, Juyoung Yoon, Engin U. Akkaya
