Review
Biotechnology & Applied Microbiology
Margarita Shleeva, Alexander Savitsky, Arseny Kaprelyants
Summary: The spread of multi-drug-resistant bacterial strains has led to the urgent need for new approaches to combat these diseases, with photodynamic inactivation (PDI) being a potentially effective alternative to antibiotics. Studies have shown that PDI can inactivate drug-resistant and dormant bacteria by generating active forms of oxygen.
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Mengfei Hou, Wandi Chen, Junkai Zhao, Deshen Dai, Mo Yang, Changqing Yi
Summary: Fluorescence imaging-guided photodynamic therapy using TCPP@PEI/PGA nanoparticles was demonstrated in this study. The nanoparticles showed excellent water-solubility, biocompatibility, in vivo bioimaging capabilities, and effective tumor cell killing upon laser irradiation.
CHINESE CHEMICAL LETTERS
(2022)
Article
Biochemistry & Molecular Biology
Katarzyna Janas, Ewa Boniewska-Bernacka, Gabriela Dyrda, Rudolf Slota
Summary: Recent investigations on targeted phototherapy for colorectal cancer have shown promising results, with porphyrins and phthalocyanines considered attractive for inhibiting cancer cell growth. Advanced molecular systems and smart drug carriers have made photodynamic therapy a viable option for treatment.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Review
Pharmacology & Pharmacy
Paromita Sarbadhikary, Blassan P. George, Heidi Abrahamse
Summary: The presence of heavy elements in photosensitizers strongly affects their properties. Conjugating photosensitizers with metals or halogens has shown promise as a strategy to improve their photodynamic properties. These compounds have been explored for various cancer therapies, including photodynamic therapy, chemotherapy, X-ray photon activation therapy, and radiotherapy. The combination of metal-based photosensitizers and X-ray irradiation is a promising approach for treating deep-seated tumors.
FRONTIERS IN PHARMACOLOGY
(2022)
Article
Oncology
Pablo Vallecorsa, Gabriela Di Venosa, M. Belen Ballatore, Dario Ferreyra, Leandro Mamone, Daniel Saenz, Gustavo Calvo, Edgardo Durantini, Adriana Casas
Summary: The study evaluated the photoactivity of four meso-substituted porphyrins and a porphyrin coupled to a fullerene in vitro. The PS with the best photokilling activity was administered to mice bearing the LM3 subcutaneously implanted adenocarcinoma. The results showed high photoactivity against LM3 mammary carcinoma cells for TAPP, DAPP, TEMCC4+ and TEMCP4+, with TAPP being the most active.
Article
Medicine, Research & Experimental
Klaudia Michalska, Michal Rychlowski, Martyna Krupinska, Grzegorz Szewczyk, Tadeusz Sarna, Joanna Nakonieczna
Summary: The study showed that gallium mesoporphyrin IX (Ga3 + MPIX) has dual functionality in antimicrobial photodynamic inactivation, disrupting iron metabolism and possessing photosensitizer properties. It efficiently destroys bacteria with relatively low toxicity to eukaryotic cells and phototoxicity.
MOLECULAR PHARMACEUTICS
(2022)
Article
Chemistry, Multidisciplinary
Francesco Armillotta, Enrico D'Incecco, Manuel Corva, Matus Stredansky, Jean-Jacques Gallet, Fabrice Bournel, Andrea Goldoni, Alberto Morgante, Erik Vesselli, Alberto Verdini
Summary: Self-metalation is a promising approach to incorporate a single metal atom in a tetrapyrrolic macrocycle within organic frameworks supported by metal surfaces. The interaction between the molecule and the surface may facilitate charge transfer and geometric distortion of the molecular plane, necessary for metal inclusion. However, the presence of an activation barrier on the metal surface can pose a challenge that may require oxygen pre-adsorption and mild annealing to overcome.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Yanyan Li, Guichen Li, Qian Zhang, Yuxia Li, Qifan Jia, Wenyuan Zhang, Xiaoxia Feng, Weibing Xu, Jiacheng Liu
Summary: Three water-soluble porphyrins containing halogen atoms (F, Cl, Br) were synthesized, with P3 showing the highest singlet oxygen generation capacity. MTT assay confirmed good phototoxicity and high selectivity of P1-P3, while fluorescence imaging and intracellular reactive oxygen species demonstrated cell apoptosis and ROS production. The high ROS production and excellent phototoxicity make the photosensitizers potential candidates for PDT drugs.
CHEMICAL PHYSICS LETTERS
(2021)
Article
Nanoscience & Nanotechnology
Carla I. M. Santos, Laura Rodriguez-Perez, Gil Goncalves, Cristina J. Dias, Fatima Monteiro, Maria do Amparo F. Faustino, Sandra Vieira, Luisa A. Helguero, Maria Angeles Herranz, Nazario Martin, M. Graca P. M. S. Neves, Jose M. G. Martinho, Ermelinda M. S. Macoas
Summary: Conjugation of porphyrins with graphene quantum dots improved internalization by cancer cells and showed promising results as phototherapeutic agents against breast cancer.
ACS APPLIED NANO MATERIALS
(2021)
Article
Chemistry, Inorganic & Nuclear
Dmitriy A. Lazovskiy, Ivan A. Skvortsov, Veronika Novakova, Pavel A. Stuzhin
Summary: Phosphorus(v) complexes of octaphenyltetrapyrazinocorrolazine with two aryloxy groups were synthesized. Complex 2a with axial PhO groups fluoresces in multiple solvents and generates singlet oxygen effectively. The introduction of NMe2 and OH groups significantly affects fluorescence parameters and photosensitizing properties, with solvent and pH sensitivity.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Claire Donohoe, Asterios Charisiadis, Sophie Maguire, Brendan Twamley, Fabio A. Schaberle, Ligia C. Gomes-da-Silva, Mathias O. Senge
Summary: The time dependence of atropisomer interconversion has hindered the development of single atropisomer drug candidates. The instability caused by moderate interconversion energy barriers is a concern for drug stability. However, there is a recent focus on developing stable atropisomer drugs with enhanced activity.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Oncology
Grazille Guidolin Rossi, Kevim Bordignon Guterres, Kelly Schneider Moreira, Thiago Augusto Lima Burgo, Marli Matiko Anraku de Campos, Bernardo Almeida Iglesias
Summary: Antimicrobial photodynamic therapy has shown potential in treating noninvasive infections, with positively charged porphyrins, especially the 3-PdTPyP derivative, demonstrating the most efficient bactericidal activity against fast-growing mycobacterial strains.
PHOTODIAGNOSIS AND PHOTODYNAMIC THERAPY
(2021)
Article
Chemistry, Multidisciplinary
Shu-ping Wang, Xuechun Huang, Yunhong He, Haotian Zhang, Jun Zhou, Guping Tang, Shijun Li, Hongzhen Bai
Summary: The development of intelligent nano-platforms with high tumor-targeting capability, enhanced solubility, and efficacious photochemotherapy is urgently demanded for clinical anticancer treatments. In this study, an amphiphilic porphyrin (P) was used to complex with camptothecin (CPT) to form supra-amphiphile-assembled nanoparticles (CPT@P). The resulting CPT@PM, with cancer cell membrane (M) camouflage, showed excellent stability, homologous targeting ability, and specific co-delivering of the chemotherapeutic drug and photosensitizer to tumor cells. This research provides a promising nanoplatform for cancer therapy by utilizing the unique structure and intrinsic performance of porphyrin photosensitizers and membrane-coating technology.
Review
Pharmacology & Pharmacy
Ana Maria Udrea, Adriana Smarandache, Andra Dinache, Catalina Mares, Simona Nistorescu, Speranta Avram, Angela Staicu
Summary: Malignant melanoma is a severe form of skin cancer with various risk factors, and photodynamic therapy using photosensitizers has shown promise in its treatment. However, the presence of melanin and its antioxidant properties can hinder the effectiveness of this therapy, leading to the exploration of new photosensitizing platforms. The use of nanotechnology has advanced the development of photosensitizers, enhancing solubility, optical absorption, and tumor targeting.
Article
Biochemistry & Molecular Biology
Dawid Lazewski, Malgorzata Kucinska, Edward Potapskiy, Joanna Kuzminska, Artur Tezyk, Lukasz Popenda, Stefan Jurga, Anna Teubert, Zofia Gdaniec, Jacek Kujawski, Katarzyna Grzyb, Tomasz Pedzinski, Marek Murias, Marcin Wierzchowski
Summary: This work focuses on the synthesis and characterization of metal-free, zinc (II), and cobalt (II) porphyrins with short PEG chains. The compounds were characterized using various spectroscopic techniques and mass spectrometry. The UV-Vis absorption bands of the compounds were determined using computational models based on DFT and TD-DFT. The compounds showed promising photosensitizing activity and were tested on different cancer cell lines. The results showed a clear structure-activity relationship between the substituents, their positions, and the central metal ions. Particularly, the metal-free and zinc derivatives exhibited strong cytotoxic activity against bladder cancer cells. Overall, this study highlights the potential application of these compounds in photodynamic therapy.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Physical
Rosilene A. Welter, Harrson Santana, Lucimara G. de la Torre, Mark Robertson, Osvaldir Pereira Taranto, Michael Oelgemoeller
Summary: Methyl oleate, a fatty acid methyl ester, was successfully produced through photoesterification of oleic acid using TO and UVA light. The main operational conditions of the reaction were evaluated and optimized. The study proposed a photoesterification mechanism and described the reaction using the Langmuir-Hinshelwood kinetic model. Thermodynamic results indicated the importance of operational conditions in supplying energy and increasing reactant miscibility.
Review
Biochemistry & Molecular Biology
Arno Wiehe, Mathias O. Senge
Summary: This review provides an overview of the research, development, and clinical applications of the photosensitizer 5,10,15,20-tetra(m-hydroxyphenyl)chlorin (mTHPC, temoporfin) in photodynamic (cancer) therapy (PDT) and other medical applications. The review covers the chemistry, biochemistry, pharmacology, and clinical applications of temoporfin, including the formulation development such as liposomal formulations. The literature covered spans from 2009 to early 2022 and is connected to a previous extensive review on this photosensitizer, which traces its development, approval, and clinical application.
PHOTOCHEMISTRY AND PHOTOBIOLOGY
(2023)
Review
Green & Sustainable Science & Technology
Michael S. A. Kamel, Ahmed Al-jumaili, Michael Oelgemoller, Mohan Jacob
Summary: Organic photovoltaics (OPVs) have emerged as a promising alternative to inorganic photovoltaics, but further improvements in efficiency are needed. This review provides a comprehensive overview of the progress in OPV performance over the past decade through the application of various inorganic nanoparticles (INPs), and analyzes the factors affecting the efficiency of OPVs.
RENEWABLE & SUSTAINABLE ENERGY REVIEWS
(2022)
Article
Chemistry, Organic
Claire Donohoe, Asterios Charisiadis, Sophie Maguire, Brendan Twamley, Fabio A. Schaberle, Ligia C. Gomes-da-Silva, Mathias O. Senge
Summary: The time dependence of atropisomer interconversion has hindered the development of single atropisomer drug candidates. The instability caused by moderate interconversion energy barriers is a concern for drug stability. However, there is a recent focus on developing stable atropisomer drugs with enhanced activity.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Biao Yang, Kaifeng Niu, Nan Cao, Nitika Grover, Wenchao Zhao, Alexander Riss, Jonas Bjoerk, Willi Auwaerter, Johannes V. Barth, Mathias O. Senge
Summary: In this study, the behavior of 1,3-disubstituted BCP moieties on metal surfaces was examined using low-temperature scanning tunneling microscopy/non-contact atomic force microscopy studies and density functional theory modeling. The configuration, supramolecular assembly, and thermally activated dehalogenative coupling reactions of BCP-containing precursors on Au(111) were investigated, resulting in the formation of polymeric chains. These findings provide sub-molecular insights into the behavior of BCP scaffolds on surfaces and expand the potential application of BCP derivatives in custom-designed surface architectures.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Nitika Grover, Maxime Cheveau, Brendan Twamley, Christopher J. Kingsbury, Cornelia M. Mattern, Mathias O. Senge
Summary: We present a two-step method for obtaining versatile bicyclo[1.1.1]pentane (BCP) derivatives using Grignard reagents. This approach allows for the incorporation of BCP units into tetrapyrrolic macrocycles, as well as the synthesis of a novel class of calix[4]pyrrole analogues by replacing bridging methylene groups with BCP units. Moreover, electron-withdrawing substituents at the BCP bridgeheads lead to the formation of a doubly N-confused system. Single-crystal X-ray diffraction analyses and 2D NMR spectroscopy reveal that the pyrrole rings in BCP-containing macrocycles exist in 1,3-alternate or alpha beta alpha beta conformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Irina Osadchuk, Hanna-Eliisa Luts, Karolis Norvaisa, Victor Borovkov, Mathias O. Senge
Summary: The determination of molecular stereochemistry and absolute configuration is important in chemistry, pharmacology, and biology. Electronic circular dichroism (ECD) is a widely used tool for chirality assignment, but the mechanisms of induced ECD in porphyrin complexes are not fully understood.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Engineering, Chemical
Rosilene Andrea Welter, Harrson Silva Santana, Lucimara Gaziola de la Torre, Mark C. Barnes, Osvaldir Pereira Taranto, Michael Oelgemoeller
Summary: Biodiesel is a large-scale eco-friendly substitute and additive to fossil fuels. Traditional methods of production have several disadvantages, leading to the exploration of alternative feedstocks, catalysts, and operational conditions. This review analyzes current biodiesel technologies and improvement strategies.
CHEMBIOENG REVIEWS
(2023)
Article
Crystallography
Harry C. Sample, Brendan Twamley, Mathias O. Senge
Summary: The crystal structures of three S-(pyridin-2-yl) benzothioesters with different para-phenyl substituents are reported. These compounds are used in the mono-acylation of pyrrolic species to produce multifunctional tetrapyrroles. The dominant interactions in the crystal packing vary from pi-pi stacking in compound 1 to exclusively C-H···O/N interactions in compound 3 as the para-phenyl motif changes from electron withdrawing to electron donating.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
(2023)
Article
Crystallography
Harry C. Sample, Brendan Twamley, Mathias O. Senge
Summary: The crystal structure of compound 1 (C26H24Br2N4O8S2) is presented in this study. Compound 1 was obtained as a by-product in the synthesis of geminal-dimethyl hydrodipyrrins. Unexpected enantiomeric resolution was observed in both the bulk sample and crystal of 1, with distinct C-H···O (C-methyl-H···O-nitro, C-sp3-H···O-sulfonyl) interactions present in the enantiomers, along with other interactions, forming a polymer along the c-axis direction. Little data is available on the 1,3-dinitrobutane scaffold, unlike the well-documented pyrrolic fragments.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Davide Ranieri, Alberto Privitera, Fabio Santanni, Karolina Urbanska, Grant J. Strachan, Brendan Twamley, Enrico Salvadori, Yu-Kai Liao, Mario Chiesa, Mathias O. Senge, Federico Totti, Lorenzo Sorace, Roberta Sessoli
Summary: By synthesizing and studying a VIVO-CuII porphyrin dimer, we observed measurable exchange coupling and good spin coherence, making it suitable for operating two-qubit molecular spin-based quantum gates under various conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Irina Osadchuk, Hanna-Eliisa Luts, Karolis Norvaisa, Victor Borovkov
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Editorial Material
Chemistry, Multidisciplinary
Irina Osadchuk, Hanna-Eliisa Luts, Karolis Norvaisa, Victor Borovkov, Mathias O. Senge
Summary: This article features the groups of Irina Osadchuk at Tallinn University of Technology and Mathias Senge at Trinity College Dublin. The image illustrates the measurement and simulation of ECD and UV-Vis spectra of a porphyrin molecule with two guest molecules (R)-camphor sulfonic acid under UV-visible light irradiation. Read the full text of the article at 10.1002/chem.202301408.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Nan Cao, Jonas Bjoerk, Eduardo Corral-Rascon, Zhi Chen, Mario Ruben, Mathias O. Senge, Johannes V. Barth, Alexander Riss
Summary: This study investigates how aromaticity affects the reactivity of alkyne-substituted porphyrin molecules on a Au(111) surface. The experiments show that carbon atoms stabilized by aromaticity display lower reactivity, which is consistent with density functional theory calculations.
Review
Chemistry, Multidisciplinary
Tomoya Ishizuka, Nitika Grover, Christopher J. Kingsbury, Hiroaki Kotani, Mathias O. Senge, Takahiko Kojima
Summary: This article summarizes the synthetic methods and design aspects of nonplanar porphyrin formation, the key properties and functionality of the nonplanar aromatic framework, and the scope and utility of this emerging class in addressing important scientific, industrial, and environmental issues.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
