Article
Biochemistry & Molecular Biology
Carolina Diaz-Norambuena, Edurne Avellanal-Zaballa, Alejandro Prieto-Castaneda, Jorge Banuelos, Santiago de la Moya, Antonia R. Agarrabeitia, Maria J. Ortiz
Summary: Heavy-atom-free photosensitizers, such as BODIPY-based orthogonal dimers with proper formyl functionalization, have the potential to visualize and kill tumor cells through fluorescence signaling and photodynamic therapy. The photophysical properties of formyl-functionalized BODIPY dimers were analyzed, indicating that their dual performance of fluorescence and singlet oxygen generation can be modulated by the formyl functionalization at specific positions. Regioselective formylation was proposed as an effective tool to balance fluorescence, singlet oxygen generation, and intramolecular charge transfer for photo-theragnosis.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Applied
Raquel C. R. Goncalves, Joao Pina, Susana P. G. Costa, M. Manuela M. Raposo
Summary: The study found that a BODIPY derivative showed a significant enhancement in singlet oxygen sensitization quantum yield with the decrease of solvent dielectric constant. Triplet state formation for the derivative was mediated by intramolecular charge transfer state in toluene, while hindered by fast recombination of the ICT state in polar solvents. The photoinduced dynamics of the BODIPY derivatives were characterized from femtosecond to nanosecond time scale using pump-probe transient absorption spectroscopy.
Article
Chemistry, Physical
Ceren Can Karanlik, Gurkan Karanlik, Ali Erdogmus
Summary: Recently, there has been increasing attention in photodynamic therapy (PDT) for cancer treatment compared to traditional methods. This study presents the synthesis of novel BODIPY derivatives for PDT applications and characterizes the compounds using various spectroscopic methods. The potential of the synthesized compounds in PDT applications was evaluated through fluorescence, singlet oxygen, and photodegradation quantum yield calculations.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(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
Ezel Ozturk Gunduz, Hande Eserci Gurbuz, Berkan Tasasiz, Elif Yildiz Gul, Esra Tanriverdi Ecik, Elif Okutan
Summary: This research focuses on the development of new photocatalysts that are active under light and suitable for organic reactions. Novel benzyl-, naphthalimide (NI)-, and carbazole (CB)-BODIPY derivatives were synthesized and characterized. These compounds exhibited strong absorption bands, moderate fluorescence characters, and good singlet-oxygen-generating abilities, making them effective photocatalysts. They were also used in the synthesis of juglone, achieving a high production yield in a short reaction time.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Ezel Ozturk Gunduz, M. Emre Gedik, Gurcan Gunaydin, Elif Okutan
Summary: The study demonstrates the successful development of efficient PDT applications against cancer using nanocarriers combined with advanced chemical molecules to generate singlet oxygen and ROS, leading to significant anti-tumor effects in vitro.
Article
Chemistry, Multidisciplinary
Suay Dartar, Muhammed Ucuncu, Erman Karakus, Yuqi Hou, Jianzhang Zhao, Mustafa Emrullahoglu
Summary: The new generation of halogen-based triplet sensitisers were developed by incorporating geminal dibromides into the pi-conjugation of BODIPY, enhancing intersystem crossing and excited triplet states.
CHEMICAL COMMUNICATIONS
(2021)
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)
Article
Chemistry, Applied
Tomas Guerrero, Fernanda Vazquez-Ortega, Irene Lagunes, Erik Ortiz-Blanco, Gabriela Sosa-Ortiz, Ricardo Tovar-Miranda, Manuel E. Medina, Angel Trigos
Summary: Hydroxycoumarins exhibit potential photosensitizing activity by promoting singlet oxygen generation and their hardness can affect the reaction. The experimental results are supported by density functional theory (DFT) calculations, confirming the pro-oxidant potential of hydroxycoumarins as photosensitizers.
Review
Chemistry, Physical
Agata Blacha-Grzechnik
Summary: Research has shown that conjugated polymers can serve as an effective light-activated source of singlet oxygen due to their high absorption and efficient energy transfer properties. These polymers with extended pi-conjugated bonds have novel possibilities to explore.
Article
Chemistry, Applied
Nidhi Tyagi, Navneet Kaur, Subash Chandra Sahoo, Paloth Venugopalan
Summary: Organometallic Re(I)-BODIPY compounds have shown promise as metal-based photosensitizers for PDT applications, with NPReL nanoparticles demonstrating enhanced cytotoxicity and potential as a PDT agent, showcasing its potential as an effective therapeutic agent.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Spectroscopy
Rodrigo C. Silva, Hilde H. Buzza, Eli S. A. Ducas, Kleber T. Oliveira, Vanderlei S. Bagnato, Guilherme R. L. Souza, Luciane M. Almeida, Pablo J. Goncalves
Summary: A supramolecular assembly of methylene blue and curcumin was synthesized and evaluated for its potential in photodynamic antiangiogenic therapy. The results demonstrated that the MB-Curc assembly exhibited a synergistic vascular effect, causing significant damage to the vascular network after irradiation.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2023)
Article
Chemistry, Medicinal
Jacob W. Campbell, Matthew T. Tung, Roberto M. Diaz-Rodriguez, Katherine N. Robertson, Andrew A. Beharry, Alison Thompson
Summary: This study reported the synthesis and characterization of a BODIPY appended to a five-membered heterocyclic tellurophene moiety, which acts as a potent photosensitizer with a mass cytometry tag. Through late-stage Suzuki-Miyaura coupling, the tellurophene-appended BODIPY was successfully synthesized, demonstrating high singlet oxygen quantum yield and cytotoxicity.
ACS MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Physical
Natalia Kiseleva, Mikhail A. Filatov, Jan C. Fischer, Milian Kaiser, Marius Jakoby, Dmitry Busko, Ian A. Howard, Bryce S. Richards, Andrey Turshatov
Summary: Triplet-triplet annihilation upconversion (TTA-UC) is an important optical process used in biophotonics, solar energy harvesting, and photochemistry. The use of heavy-atom-free sensitizers in TTA-UC is a challenge, but it has been found that certain sensitizers can still achieve efficient intersystem crossing and high quantum yields of upconversion luminescence under specific conditions.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Multidisciplinary Sciences
Duy Khuong Mai, Chanwoo Kim, Joomin Lee, Temmy Pegarro Vales, Isabel Wen Badon, Koushitak De, Sung Cho, Jaesung Yang, Ho-Joong Kim
Summary: By modifying the substituents in lactose-modified BODIPY photosensitizers, the photophysical properties and photodynamic anticancer activities of the sensitizers can be controlled. The substituents have different effects on fluorescence and singlet oxygen generation capability.
SCIENTIFIC REPORTS
(2022)
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
Busra Can, Yusuf Cakmak
Summary: This study reports the synthesis and photophysical investigations of two different near IR absorbing classes of Boron dipyrromethene (Bodipy) photosensitizers for use in Photodynamic therapy (PDT) and fluorescent bioimaging purposes. The benzofused Bodipy derivative was found to be an effective PDT agent, while the unique distyryl derivative showed better singlet oxygen generation ability.
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
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, Physical
Mutahire Tok, Busra Say, Gamze Dolek, Beytullah Tatar, Derya Oncel Ozgur, Cisem Kirbiyik Kurukavak, Mahmut Kus, Yavuz Dede, Yusuf Cakmak
Summary: In this research, four new conjugated Bodipy structures were synthesized and investigated. The photovoltaic performance was found to be largely affected by the units on the meso position under the compounds studied and the electronic distributions of the frontier molecular orbitals. These studies contribute to the implementation of these compounds in near infrared photovoltaics.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(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
Chemistry, Medicinal
Busra Say, Beytullah Tatar, Betul Uzulmez, Melike Ebrar Bakirci, Gulcihan Gulseren, Yusuf Cakmak
Summary: Three unique hydrazone-based small-molecule-activatable photosensitizers were designed and synthesized. Two of them showed efficient performance in a low-pH environment, mimicking the microenvironment of cancerous tissues. The activation pathway is distinctive and relies on hydrazone bond cleavage. In vitro cellular studies using aggressive cancer lines and tumor-specific culture conditions successfully triggered the cleavage and activation of cytotoxic singlet oxygen production within the appropriate time frame. Additionally, the intriguing photophysical characteristics of alpha- and beta-substituted hydrazone derivatives of the Bodipy structures and their mild hydrolysis methods were also successfully investigated.
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)
Review
Chemistry, Multidisciplinary
Huriye Ilhan, Yusuf Cakmak
Summary: BODIPY dyes are highly useful compounds with rich photophysical properties, stability, and ease of functionalization. Recent research has focused on targeted photodynamic therapy, photothermal therapy, fluorescent bioimaging agents, structural modification of the BODIPY core, synthesis of BODIPY analogs, and BODIPY-based supramolecular constructs. This review summarizes the advances in BODIPY structures substituted with carbon-nitrogen double bonds for various applications, including fluorescent indicators, pharmaceutical applications, photodynamic therapy, fluorescent switches, and building blocks.
TOPICS IN CURRENT CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yusuf Cakmak
Summary: This work reports the synthesis, photophysical, and electrochemical properties of hexyl thiophene substituted thieno[b]-fused BODIPY structure. One of the derivatives, HTFBod, is a rare compound with a maximum absorbance wavelength greater than 750 nm among fused BODIPY compounds while maintaining high molar absorptivity and fluorescence quantum yield. The compound shows potential as a donor compound for organic solar cells due to its low band gap and ability to harvest near-IR light, as well as its air stability and solubility.
TURKISH JOURNAL OF CHEMISTRY
(2022)
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, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
