Article
Biochemistry & Molecular Biology
Ainhoa Oliden-Sanchez, Enrique Alvarado-Martinez, Diana E. E. Ramirez-Ornelas, Miguel A. A. Vazquez, Edurne Avellanal-Zaballa, Jorge Banuelos, Eduardo Pena-Cabrera
Summary: In this study, a synthetic method for a new set of π-extended BODIPY derivatives was reported, which involved the selective functionalization of the meso-position and the halogenated sites using the Liebeskind-Srogl cross-coupling and Suzuki reactions. All these laser dyes exhibited absorption and emission bands in the red edge of the visible spectrum, with the thiophene-containing compounds showing the highest emission efficiency. The fluorescence and laser efficiency of the polyphenylBODIPYs could be further enhanced by decorating the peripheral phenyls with electron donor/acceptor groups. Surprisingly, the polythiopheneBODIPYs demonstrated excellent laser performance despite their charge transfer character. Thus, these BODIPY derivatives offer a palette of stable and bright laser sources covering the spectral range from 610 nm to 750 nm.
Article
Chemistry, Applied
Hui Li, Hanming Dai, Anqing Mei, Xiaohong Ruan, Weili Wang, Dongliang Yang, Wenjun Wang, Qi Zhang, Xiaochen Dong, Jinjun Shao
Summary: In this study, a small molecular fluorescent dye based on boron difluoride formazanate and encapsulated into nanoparticles was successfully synthesized. The nanoparticles showed high fluorescence quantum yield and photothermal conversion efficiency in the NIR-II region, making them promising for cancer therapy.
Article
Chemistry, Multidisciplinary
Joao Felicidade, Fabio M. F. Santos, Jesus F. Arteaga, Patricia Remon, Rene Campos-Gonzalez, Ha-Chi Nguyen, Francisco Najera, Francisco Bosca, David Y. W. Ng, Pedro M. P. Gois, Uwe Pischel
Summary: A series of boronic-acid-derived salicylidenehydrazone (BASHY) complexes were synthesized in good yields through a versatile three-component reaction. These complexes exhibit fluorescence switching behavior by photoinduced electron transfer, which can be controlled by the addition of acid. In organic solvent, the fluorescence is observed in the green-to-orange region, while in water under physiological pH conditions, the fluorescence is observed in the red-to-NIR region with appreciable quantum yields and lifetimes. These characteristics make these dyes suitable for fluorescence lifetime imaging of live cells.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Alexander Schulz, Frank Wuerthner
Summary: This study demonstrated a significant fluorescence enhancement for a weakly fluorescent merocyanine dye by co facially stacking it with other dyes in heterofolda-trimer architectures. This enhancement was explained by the rigidification of the emitting chromophore in the foldamer architecture and the presence of a non forbidden lowest exciton state in H-coupled heteroaggregates, suggesting a promising strategy for improved fluorophores inspired by nature's green fluorescent protein (GFP).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Gana Sanil, Maciej Krzeszewski, Wojciech Chaladaj, Witold Danikiewicz, Iryna Knysh, Lukasz Dobrzycki, Olga Staszewska-Krajewska, Michal K. Cyranski, Denis Jacquemin, Daniel T. Gryko
Summary: This study presents the tandem intramolecular hydroarylation of alkynes accompanied by a 1,2-aryl shift. By utilizing the unique electron-rich character of the 1,4-dihydropyrrolo[3,2-b]pyrrole scaffold, pi-expanded, centrosymmetric pyrrolo[3,2-b]pyrroles were synthesized by reacting alkynes at the already occupied positions 2 and 5. The reaction only proceeds in the presence of cationic gold catalyst and produces unknown compounds with six conjugated rings. These synthesized compounds have potential applications in the creation of new materials with various functionalities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Leonardo Andreoni, Federica Cester Bonati, Jessica Groppi, Davide Balestri, Gianpiero Cera, Alberto Credi, Andrea Secchi, Serena Silvi
Summary: We synthesized and characterized [2]rotaxanes based on a stilbazolium dye and a calix[6]arene macrocycle. Due to the non-symmetry of both components, two orientational isomers were obtained. The two isomers exhibited distinct photophysical and photochemical properties in solution and solid state, surpassing the unencapsulated dye.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Kilian Colas, Karl O. Holmberg, Linus Chiang, Susanne Doloczki, Fredrik J. Swartling, Christine Dyrager
Summary: This study conducted an extensive photophysical investigation of fluorescent derivatives and their ability to specifically image lipid droplets, proving them to be effective probes for detecting lipid deposits in both healthy and cancerous brain cells. Furthermore, all compounds in the series were predicted to cross the blood-brain barrier, opening up possibilities for future in vivo studies exploring the role of lipid droplets in the central nervous system.
Article
Chemistry, Multidisciplinary
Fabien Ceugniet, Quentin Huaulme, Alexandra Sutter, Denis Jacquemin, Nicolas Leclerc, Gilles Ulrich
Summary: This article reports the synthesis and properties of heterosubstituted alpha beta-fused BODIPY fluorophores. The compounds were synthesized from 2,3,5,6-tetrahalo-BODIPY through sequential and selective Stille cross-coupling reactions, allowing the introduction of different substituents at specific positions on the BODIPY ring. The fully fused compounds showed a bathochromically shifted emission and a hyperchromic shift of the absorption maxima, with relatively high fluorescence quantum yields. Computational studies were conducted to gain a comprehensive understanding of the photophysical behavior of these dyes.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Juan S. Rocha-Ortiz, Alberto Insuasty, Duvalier Madrid-Usuga, Ana G. Mora-Leon, Alejandro Ortiz
Summary: The three new triphenylamine-BODIPY dyads BDPT1-3 exhibit strong electronic interactions between donor and acceptor moieties, high sensitivity to alkoxy groups, and promising properties for application in organic photovoltaic or light emitting devices.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mengyao Zhao, Jianbo Wang, Zuhai Lei, Lingfei Lu, Shangfeng Wang, Hongxin Zhang, Benhao Li, Fan Zhang
Summary: The newly developed pTAS sensors can achieve high sensitivity tumor pH monitoring within a wider response region, extending the pH detection range. Through dual-channel ratiometric bioimaging, the dynamic changes in tumor pH can be visualized in vivo.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Ming-Ho Liu, Zhe Zhang, Yu-Chi Yang, Yang-Hsiang Chan
Summary: This study presents semiconductor polymers with emission characteristics in the NIR-IIa window, which show potential for high-resolution, noninvasive brain imaging in live mice and offer a platform for future design of NIR-IIa or even NIR-IIb emitting Pdots.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Kilian Colas, Susanne Doloczki, Mauricio Posada Urrutia, Christine Dyrager
Summary: This minireview discusses the synthesis, structure-photophysical properties relationship, and bioimaging applications of fluorescent coumarins, xanthenes, BODIPYs, and cyanines. Advantages and disadvantages of the emissive units are also explored, along with general practical considerations when using fluorophores in a biological context.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yuta Kudoh, Emi Suzuki, Hikari Ochiai, Kakeru Ise, Yoshifumi Kimura, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano
Summary: The properties of azaporphyrins can be modulated by changing the number of meso-nitrogen atoms. This study reports the synthesis of the first examples of 5,10,15,20-tetraaryl-5-azaporphyrinium (MTAMAP) salts. The inclusion of one meso-nitrogen atom significantly changes the properties of the porphyrin ring, making MTAMAP salts promising for the development of new fluorophores and photosensitizers.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Yogajivan Rout, Jean Michel Merkes, Srinivas Banala, Rajneesh Misra
Summary: Photoacoustic imaging (PAI) is a non-invasive imaging technique with great application potential in medical diagnosis. Organic chromophores and inorganic nanoparticles are widely used as contrast agents. In this study, we propose an extended conjugated organic chromophore system to enhance the photoacoustic signal by modifying the absorption spectrum and quenching the fluorescence emission.
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Manuel Weh, Jessica Ruehe, Benedikt Herbert, Ana-Maria Krause, Frank Wuerthner
Summary: The deracemization process of a racemic mixture of chiral molecules into enantioenriched compounds is achieved by an inherently chiral perylene bisimide cyclophane, which can transform [5]-helicene into an enantioenriched mixture with a high enantiomeric excess. The macrocyclic supramolecular host shows strong and enantioselective binding towards homochiral carbohelicenes, suggesting potential applications in template-catalyzed deracemization processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Instruments & Instrumentation
Snezana Dordevic, Maria Medel Gonzalez, Inmaculada Conejos-Sanchez, Barbara Carreira, Sabina Pozzi, Rita C. Acurcio, Ronit Satchi-Fainaro, Helena F. Florindo, Maria J. Vicent
Summary: The field of nanomedicine faces challenges in regulatory clarity and consistency. Developing nanomedicines requires considerations of critical quality attributes, appropriate analytical methods, important process parameters, and pre-clinical models. Close collaboration with regulatory agencies is advised to accelerate the development of future nanomedicines.
DRUG DELIVERY AND TRANSLATIONAL RESEARCH
(2022)
Editorial Material
Pharmacology & Pharmacy
Ronit Satchi-Fainaro, Helena F. Florindo, Maria J. Vicent
ADVANCED DRUG DELIVERY REVIEWS
(2022)
Article
Biochemistry & Molecular Biology
Maria J. S. A. Silva, Robin Vinck, Youchao Wang, Bruno Saubamea, Mickael Tharaud, Elena Dominguez-Jurado, Johannes Karges, Pedro M. P. Gois, Gilles Gasser
Summary: An increasing number of novel Ru(II) polypyridyl complexes have been successfully applied as photosensitizers (PSs) for photodynamic therapy (PDT). Classical maleimide and versatile NHS-activated acrylamide strategies were employed to conjugate a promising Ru(II) polypyridyl complex to the N-terminally Cys-modified Bombesin (BBN) targeting unit. Although lacking in tumoral selectivity, the new bioconjugates showed high phototoxic activity and decreased toxicity in the absence of light irradiation, making them potentially useful for advanced cancer treatment.
Article
Chemistry, Multidisciplinary
Tingxiang Yang, Abha Valavalkar, Antonio Romero-Arenas, Anindita Dasgupta, Patrick Then, Avinash Chettri, Christian Eggeling, Abel Ros, Uwe Pischel, Benjamin Dietzek-Ivansic
Summary: In this study, two four-coordinate organoboron N,C-chelate complexes with different functional terminals on the PEG chains were investigated for their photophysical properties in human MCF-7 cells. The excited-state relaxation dynamics were similar in DMSO, but aggregation was observed in water for the complexes with carboxylate terminal group. In cellulo studies showed different features depending on the nature of the anchoring PEG chains, with shorter lifetimes of charge-transfer state in cellulo compared to DMSO for complexes with an amino group.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Antonio Dominguez-Alfaro, Vania F. Pais, David B. Guzman-Rios, Daniel Collado, Francisco Najera, Ezequiel Perez-Inestrosa, Uwe Pischel
Summary: A bichromophoric dyad composed of a Prodan-derived moiety and a BODIPY dye was synthesized and characterized for multiphoton fluorescence microscopy of N13 microglial cells. The efficient energy transfer of the dyad was observed independent of solvent polarity, but in polar media, photoinduced electron transfer competed with energy transfer. The Prodan-derived chromophore also exhibited significant two-photon absorption, making it suitable as a sensitization antenna for BODIPY fluorescence.
Article
Chemistry, Physical
Miroslav Dangalov, Adolfo Fernandez-Figueiras, Martin A. Ravutsov, Ekaterina Vakarelska, Maya K. Marinova, Nuno R. Candeias, Svilen P. Simeonov
Summary: A Ru-catalyzed isomerization reaction of Achmatowicz derivatives is reported, providing unexplored routes for diversification of the biogenic furanic platform. Mechanistic insights were studied using computational and deuterium labeling techniques. This transformation proved to be a robust tool for the synthesis of bioderived monomers and 4-keto-o-valerolactones, enabling the flexible synthesis of acetogenins. Additionally, a concise and protective group-free asymmetric total synthesis of two natural products, (S,S)-muricatacin and (S,S)-L-factor, is described.
Article
Oncology
Akshaya Murugesan, Sana Kari, Anita Shrestha, Benedicta Assoah, Konda Mani Saravanan, Monica Murugesan, Ramesh Thiyagarajan, Nuno R. Candeias, Meenakshisundaram Kandhavelu
Summary: A novel library of dioxocin derivatives was developed as glutaminase inhibitors for treating glioblastoma. These compounds exhibited significant growth inhibition effect in glioblastoma cells and showed stronger anti-tumor activity compared to the standard drug temozolomide. The most promising compound interacted with key residues of glutaminase and demonstrated potential anti-proliferative properties.
Article
Chemistry, Multidisciplinary
Jialei Chen-Wu, David B. Guzman-Rios, Patricia Remon, Jose A. Gonzalez-Delgado, Antonio J. Martinez-Martinez, Francisco Najera, Jesus F. Arteaga, Uwe Pischel
Summary: A series of dithienylethene (DTE) photoswitches with aza-heteroaromatic cationic moieties were synthesized and characterized for their photochemical and photophysical properties. The efficiency of switching and the composition of photostationary states depended on the degree of pi-conjugation of the heteroaromatic systems. Fine-tuning of fluorescence emission was achieved through pi-conjugation, with DTEs containing acridinium moieties emitting in the red spectral region. The electrocyclic ring-closing reaction resulted in an ON-OFF fluorescence switching.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Joao Felicidade, Fabio M. F. Santos, Jesus F. Arteaga, Patricia Remon, Rene Campos-Gonzalez, Ha-Chi Nguyen, Francisco Najera, Francisco Bosca, David Y. W. Ng, Pedro M. P. Gois, Uwe Pischel
Summary: A series of boronic-acid-derived salicylidenehydrazone (BASHY) complexes were synthesized in good yields through a versatile three-component reaction. These complexes exhibit fluorescence switching behavior by photoinduced electron transfer, which can be controlled by the addition of acid. In organic solvent, the fluorescence is observed in the green-to-orange region, while in water under physiological pH conditions, the fluorescence is observed in the red-to-NIR region with appreciable quantum yields and lifetimes. These characteristics make these dyes suitable for fluorescence lifetime imaging of live cells.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Meeting Abstract
Endocrinology & Metabolism
J. Marques, R. Nunes, M. Carvalho, J. Neves, H. Florindo, D. Ferreira, B. Sarmento
DIABETES RESEARCH AND CLINICAL PRACTICE
(2023)
Article
Infectious Diseases
David Pires, Manoj Mandal, Ana I. Matos, Carina Peres, Maria Joao Catalao, Jose Miguel Azevedo-Pereira, Ronit Satchi-Fainaro, Helena F. Florindo, Elsa Anes
Summary: The golden age of antibiotics for tuberculosis in the 1950s has been overshadowed by the ongoing challenges in controlling the disease and the increasing global antibiotic resistance. Understanding the interactions between TB bacteria and their host can lead to the development of better therapeutics, such as vaccines and host-directed therapies. In this study, a potential nanomedicine based on chitosan (CS-DS) was developed to deliver siRNA targeting cystatin C to infected macrophages, resulting in improved immune responses and decreased intracellular survival of TB bacilli, including drug-resistant strains. These findings suggest the potential adjunctive use of CS-DS in TB therapy, either alone or in combination with antibiotics.
Article
Chemistry, Multidisciplinary
Ana I. I. Matos, Carina Peres, Barbara Carreira, Liane I. F. Moura, Rita C. C. Acurcio, Theresa Vogel, Erik Wegener, Filipa Ribeiro, Marta B. B. Afonso, Fabio M. F. Santos, Agueda Martinez-Barriocanal, Diego Arango, Ana S. S. Viana, Pedro M. P. Gois, Liana C. C. Silva, Cecilia M. P. Rodrigues, Luis Graca, Rainer Jordan, Ronit Satchi-Fainaro, Helena F. F. Florindo
Summary: Activation of host immunity by using a POx-PLGA nanovaccine to modulate TAM function and block PD-1, combined with the delivery of peptide antigens, adjuvants, and regulators of TGF-β expression, provides an alternative approach for cancer immunotherapy.
Article
Chemistry, Multidisciplinary
Jialei Chen-Wu, Patricia Maximo, Patricia Remon, A. Jorge Parola, Nuno Basilio, Uwe Pischel
Summary: The tailored design of a light-triggered supramolecular cascade allows for the transduction of photons into chemical communication and the release of a neurotransmitter, reminiscent of crucial steps in natural vision process.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Rene Campos-Gonzalez, Pablo Vazquez-Dominguez, Patricia Remon, Francisco Najera, Daniel Collado, Ezequiel Perez-Inestrosa, Francisco Bosca, Abel Ros, Uwe Pischel
Summary: Conveniently modified polycyclic aromatic hydrocarbon (PAH) fluorophores with red-shifted absorption and emission properties and two-photon absorption have been synthesized. The rigid structure of the dyes inhibits non-radiative deactivation and allows for the observation of fluorescence and excited triplet-state formation. These dyes are ideal bimodal chromophores for fluorescence and photosensitization.
ORGANIC CHEMISTRY FRONTIERS
(2022)
