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2. In Situ Bioconjugation of a Maleimide-Functionalized Ruthenium-Based Photosensitizer to Albumin for Photodynamic Therapy

Author

Vinck, Robin, primary, Dömötör, Orsolya, additional, Karges, Johannes, additional, Jakubaszek, Marta, additional, Seguin, Johanne, additional, Tharaud, Mickaël, additional, Guérineau, Vincent, additional, Cariou, Kevin, additional, Mignet, Nathalie, additional, Enyedy, Éva A., additional, and Gasser, Gilles, additional

Published
2023
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3. In SituBioconjugation of a Maleimide-Functionalized Ruthenium-Based Photosensitizer to Albumin for Photodynamic Therapy

Author

Vinck, Robin, Dömötör, Orsolya, Karges, Johannes, Jakubaszek, Marta, Seguin, Johanne, Tharaud, Mickaël, Guérineau, Vincent, Cariou, Kevin, Mignet, Nathalie, Enyedy, Éva A., and Gasser, Gilles

Abstract

Maleimide-containing prodrugs can quickly and selectively react with circulating serum albumin following their injection in the bloodstream. The drug–albumin complex then benefits from longer blood circulation times and better tumor accumulation. Herein, we have applied this strategy to a previously reported highly phototoxic Ru polypyridyl complex-based photosensitizer to increase its accumulation at the tumor, reduce off-target cytotoxicity, and therefore improve its pharmacological profile. Specifically, two complexes were synthesized bearing a maleimide group: one complex with the maleimide directly incorporated into the bipyridyl ligand, and the other has a hydrophilic linker between the ligand and the maleimide group. Their interaction with albumin was studied in-depth, revealing their ability to efficiently bind both covalently and noncovalently to the plasma protein. A crucial finding is that the maleimide-functionalized complexes exhibited significantly lower cytotoxicity in noncancerous cells under dark conditions compared to the nonfunctionalized complex, which is a highly desirable property for a photosensitizer. The binding to albumin also led to a decrease in the phototoxicity of the Ru bioconjugates in comparison to the nonfunctionalized complex, probably due to a decreased cellular uptake. Unfortunately, this decrease in phototoxicity was not compensated by a dramatic increase in tumor accumulation, as was demonstrated in a tumor-bearing mouse model using inductively coupled plasma mass spectrometry (ICP-MS) studies. Consequently, this study provides valuable insight into the future design of in situalbumin-binding complexes for photodynamic therapy in order to maximize their effectiveness and realize their full potential.

Published
2023
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4. Ruthenium(II) Complex Containing a Redox-Active Semiquinonate Ligand as a Potential Chemotherapeutic Agent: From Synthesis toIn VivoStudies

Author

Notaro, Anna, primary, Frei, Angelo, additional, Rubbiani, Riccardo, additional, Jakubaszek, Marta, additional, Basu, Uttara, additional, Koch, Severin, additional, Mari, Cristina, additional, Dotou, Mazzarine, additional, Blacque, Olivier, additional, Gouyon, Jérémie, additional, Bedioui, Fethi, additional, Rotthowe, Nils, additional, Winter, Rainer F., additional, Goud, Bruno, additional, Ferrari, Stefano, additional, Tharaud, Mickaël, additional, Řezáčová, Martina, additional, Humajová, Jana, additional, Tomšík, Pavel, additional, and Gasser, Gilles, additional

Published
2020
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6. Mechanisms of action of Ru(II) polypyridyl complexes as photodynamic therapy photosensitizers and chemotherapy agents

Author

Jakubaszek, Marta, STAR, ABES, Institute of Chemistry for Life and Health Sciences (iCLeHS), Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris sciences et lettres, and Gilles Gasser

Subjects
Pdt, [CHIM.THER] Chemical Sciences/Medicinal Chemistry, Ruthénium, Mechanisms, Mecanismes, Chemotherapy, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Ruthenium, Chimiothérapie
Abstract

Nowadays chemotherapy is the most common therapy used to treat cancer. Currently employed drugs are not ideal, and there is a need for new chemotherapeutics. Photodynamic therapy (PDT) is a succesful alternative or complimentary treatment to chemotherapy, radiotherapy and surgery. This medical technique involves non-toxic photosensitiser (PS) which after irradiation with specific and defined wavelenght can react with molecular oxygen or other biological substrates. As a result very reactive oxygen species or radicals are created, leading to impairment of metabolic pathways and eventually to cell death. Ru(II) polypyridyl complexes are promising chemotherapeutics as well as photosensitisers for PDT. Aim of this thesis is to understand how Ru(II)complexes excert their action in living cells. Understanding mechanisms in which photosensitizers or chemotherpeutics are acting is an important step in designing new, better compounds suitable for chemotherapy and/or for PDT., Cette thèse de doctorat a pour dessain d’évaluer d’un point de vue chimique, mais surtout biologique les complexes polypyridyle Ru (II). Ces complexes métalliques peuvent être utilisés comme photosensibilisateurs (PS) pour la thérapie photodynamique (PDT), ou encore comme agents chimiothérapeutiques dans le traitement du cancer. La PDT est un traitement alternatif ou complémentaire à la chirurgie, la chimiothérapie ou la radiothérapie.Ses nombreux avantages lui confèrent un intêret dans le traitement actuel du cancer. Son contrôle spatial et temporel est particulièrement intéressant, ce qui conduit à cibler les tumeurs tout en préservant les tissus sains. De plus, les résistances à répétition et les effets secondaires graves provoqués par la chimiothérapie incitent le monde scientifique à rechercher de nouveaux médicaments candidats anticancéreux. Les complexes de ruthénium sont l'un des groupes les plus prometteurs de médicaments candidats à base de métaux (comme chimiothérapeutiques ou PS) en raison de leurs multiples états d'oxydation stables. Cette thèse décrit un aperçu des modes d'action connus des complexes polypyridyle Ru (II) comme PS pour la PDT et introduit de nouveaux complexes, qui peuvent être utilisés pour des traitements PDT réguliers et ciblés. En outre, cette thèse se concentre également sur la caractérisation d'une nouvelle classe de complexes Ru générés comme agents anticancéreux potentiels pour la chimiothérapie, par coordination de différents dioxoligands au noyau métallique.

Published
2020

8. Rationally Designed Long-Wavelength Absorbing Ru(II) Polypyridyl Complexes as Photosensitizers for Photodynamic Therapy

Author

Karges, Johannes, Heinemann, Franz, Jakubaszek, Marta, Maschietto, Federica, Subecz, Chloé, Dotou, Mazzarine, Vinck, Robin, Blacque, Olivier; https://orcid.org/0000-0001-9857-4042, Tharaud, Mickaël, Goud, Bruno, Viñuelas Zahínos, Emilio; https://orcid.org/0000-0003-0634-1829, Spingler, Bernhard; https://orcid.org/0000-0003-3402-2016, Ciofini, Ilaria, Gasser, Gilles; https://orcid.org/0000-0002-4244-5097, Karges, Johannes, Heinemann, Franz, Jakubaszek, Marta, Maschietto, Federica, Subecz, Chloé, Dotou, Mazzarine, Vinck, Robin, Blacque, Olivier; https://orcid.org/0000-0001-9857-4042, Tharaud, Mickaël, Goud, Bruno, Viñuelas Zahínos, Emilio; https://orcid.org/0000-0003-0634-1829, Spingler, Bernhard; https://orcid.org/0000-0003-3402-2016, Ciofini, Ilaria, and Gasser, Gilles; https://orcid.org/0000-0002-4244-5097

Abstract

The utilization of photodynamic therapy (PDT) for the treatment of various types of cancer has gained increasing attention over the last decades. Despite the clinical success of approved photosensitizers (PSs), their application is sometimes limited due to poor water solubility, aggregation, photodegradation, and slow clearance from the body. To overcome these drawbacks, research efforts are devoted toward the development of metal complexes and especially Ru(II) polypyridine complexes based on their attractive photophysical and biological properties. Despite the recent research developments, the vast majority of complexes utilize blue or UV-A light to obtain a PDT effect, limiting the penetration depth inside tissues and, therefore, the possibility to treat deep-seated or large tumors. To circumvent these drawbacks, we present the first example of a DFT guided search for efficient PDT PSs with a substantial spectral red shift toward the biological spectral window. Thanks to this design, we have unveiled a Ru(II) polypyridine complex that causes phototoxicity in the very low micromolar to nanomolar range at clinically relevant 595 nm, in monolayer cells as well as in 3D multicellular tumor spheroids.

Published
2020

9. A Maltol‐Containing Ruthenium Polypyridyl Complex as a Potential Anticancer Agent

Author

Notaro, Anna, primary, Jakubaszek, Marta, additional, Koch, Severin, additional, Rubbiani, Riccardo, additional, Dömötör, Orsolya, additional, Enyedy, Éva A., additional, Dotou, Mazzarine, additional, Bedioui, Fethi, additional, Tharaud, Mickaël, additional, Goud, Bruno, additional, Ferrari, Stefano, additional, Alessio, Enzo, additional, and Gasser, Gilles, additional

Published
2020
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11. Rationally Designed Long-Wavelength Absorbing Ru(II) Polypyridyl Complexes as Photosensitizers for Photodynamic Therapy

Author

Karges, Johannes, primary, Heinemann, Franz, additional, Jakubaszek, Marta, additional, Maschietto, Federica, additional, Subecz, Chloé, additional, Dotou, Mazzarine, additional, Vinck, Robin, additional, Blacque, Olivier, additional, Tharaud, Mickaël, additional, Goud, Bruno, additional, Viñuelas Zahı́nos, Emilio, additional, Spingler, Bernhard, additional, Ciofini, Ilaria, additional, and Gasser, Gilles, additional

Published
2020
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12. Increasing the Cytotoxicity of Ru(II) Polypyridyl Complexes by Tuning the Electronic Structure of Dioxo Ligands

Author

Notaro, Anna, primary, Jakubaszek, Marta, additional, Rotthowe, Nils, additional, Maschietto, Federica, additional, Vinck, Robin, additional, Felder, Patrick S., additional, Goud, Bruno, additional, Tharaud, Mickaël, additional, Ciofini, Ilaria, additional, Bedioui, Fethi, additional, Winter, Rainer F., additional, and Gasser, Gilles, additional

Published
2020
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14. Ruthenium-initiated polymerization of lactide: a route to remarkable cellular uptake for photodynamic therapy of cancer

Author

Soliman, Nancy, primary, McKenzie, Luke K., additional, Karges, Johannes, additional, Bertrand, Emilie, additional, Tharaud, Mickaël, additional, Jakubaszek, Marta, additional, Guérineau, Vincent, additional, Goud, Bruno, additional, Hollenstein, Marcel, additional, Gasser, Gilles, additional, and Thomas, Christophe M., additional

Published
2020
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15. Mechanisms of action of Ru(ii) polypyridyl complexes in living cells upon light irradiation

Author

Jakubaszek, Marta, Goud, Bruno, Ferrari, Stefano, Gasser, Gilles, University of Zurich, and Gasser, Gilles

Subjects
1503 Catalysis, 10061 Institute of Molecular Cancer Research, 2508 Surfaces, Coatings and Films, 2506 Metals and Alloys, 570 Life sciences, biology, 2504 Electronic, Optical and Magnetic Materials, 610 Medicine & health, 2503 Ceramics and Composites, 1600 General Chemistry, 2505 Materials Chemistry
Published
2018
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16. Rationally Designed Long-Wavelength Absorbing Ru(II) Polypyridyl Complexes as Photosensitizers for Photodynamic Therapy

Author

Karges, Johannes, primary, Heinemann, Franz, primary, Jakubaszek, Marta, primary, Maschietto, Federica, primary, Subecz, Chloé, primary, Dotou, Mazzarine, primary, Blacque, Olivier, primary, Tharaud, Mickaël, primary, Goud, Bruno, primary, Vinuelas Zahinos, Emilio, primary, Spingler, Bernhard, primary, Ciofini, Ilaria, primary, and Gasser, Gilles, primary

Published
2019
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20. Encapsulation of a Ruthenium(II) Complex in Polylactide Nanoparticles: A Route to Remarkable Cellular Uptake for Photodynamic Therapy of Cancer

Author

Soliman, Nancy, primary, McKenzie, Luke K., primary, Karges, Johannes, primary, Bertrand, Emilie, primary, Tharaud, Mickaël, primary, Jakubaszek, Marta, primary, Guérineau, Vincent, primary, Goud, Bruno, primary, Hollenstein, Marcel, primary, Gasser, Gilles, primary, and Thomas, Christophe M., primary

Published
2019
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21. A Ruthenium(II) Complex Containing a Redox-Active Semiquinonate Ligand as Potential Chemotherapeutic Agent: From Synthesis to In Vivo Studies

Author

Notaro, Anna, primary, Frei, Angelo, additional, Rubbiani, Riccardo, additional, Jakubaszek, Marta, additional, Basu, Uttara, additional, Koch, Severin, additional, Mari, Cristina, additional, Dotou, Mazzarine, additional, Blacque, Olivier, additional, Gouyon, Jérémie, additional, Bedioui, Fethi, additional, Rotthowe, Nils, additional, Winter, Rainer F., additional, Goud, Bruno, additional, Ferrari, Stefano, additional, Tharaud, Mickaël, additional, Řezáčová, Martina, additional, Humajová, Jana, additional, Tomšík, Pavel, additional, and Gasser, Gilles, additional

Published
2019
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23. Evaluation of the potential of cobalamin derivatives bearing ru(ii) polypyridyl complexes as photosensitizers for photodynamic therapy

Author

Jakubaszek, Marta, Rossier, Jeremie, Karges, Johannes, Delasoie, Joachim, Goud, Bruno, Gasser, Gilles, Zobi, Fabio, Jakubaszek, Marta, Rossier, Jeremie, Karges, Johannes, Delasoie, Joachim, Goud, Bruno, Gasser, Gilles, and Zobi, Fabio

Abstract

The current photosensitizers (PSs) for photodynamic therapy (PDT) lack selectivity for cancer cells. To tackle this drawback, in view of selective cancer delivery, we envisioned conjugating two ruthenium polypyridyl complexes to vitamin B12 (Cobalamin, Cbl) to take advantage of the solubility and active uptake of the latter. Ultimately, our results showed that the transcobalamin pathway is unlikely involved for the delivery of these ruthenium‐based PDT PSs, emphasizing the difficulty in successfully delivering metal complexes to cancer cells.

Published
2019

24. FeIII–Salen‐Based Probes for the Selective and Sensitive Detection of E450 in Foodstuff.

Author

Yadav, Prerna, Jakubaszek, Marta, Spingler, Bernhard, Goud, Bruno, Gasser, Gilles, and Zelder, Felix

Subjects
*VASCULAR diseases, *CALCIFICATION, *ADENOSINE triphosphate, *PYROPHOSPHATES
Abstract

Inorganic pyrophosphate (PPi) is considered as a diagnostic marker for various diseases such as cancer and vascular calcification. PPi also plays an important preservative role as an additive E450 in foodstuff. In this work, a selective FeIII–salen‐based probe for PPi is described; this probe disassembles in the presence of the target analyte into its molecular blocks, 1,2‐propanediamine and 3‐chloro‐5‐formyl‐4‐hydroxybenzenesulfonic acid. The latter signaling unit leads to a fluorometric response. Compared with a related prototype, the new complex shows a 2.3‐times stronger emission at 500 nm and a 155‐times better selectivity of PPi over adenosine triphosphate (ATP). Importantly, the new probe was successfully applied for detecting E450 in foodstuff. [ABSTRACT FROM AUTHOR]

Published
2020
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27. Retention of CENP‐A nucleosomes during DNA replication

Author

Zasadzinska, Ewelina, primary, Huang, Jiehuan, additional, Bailey, Aaron O., additional, Lee, Nancy S., additional, Wong, Kelvin A., additional, Jakubaszek, Marta R., additional, Guo, Lucie, additional, Black, Ben E., additional, and Foltz, Daniel R., additional

Published
2017
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28. Ruthenium(II) Complex Containing a Redox-Active Semiquinonate Ligand as a Potential Chemotherapeutic Agent: From Synthesis to In VivoStudies

Author

Notaro, Anna, Frei, Angelo, Rubbiani, Riccardo, Jakubaszek, Marta, Basu, Uttara, Koch, Severin, Mari, Cristina, Dotou, Mazzarine, Blacque, Olivier, Gouyon, Jérémie, Bedioui, Fethi, Rotthowe, Nils, Winter, Rainer F., Goud, Bruno, Ferrari, Stefano, Tharaud, Mickaël, Řezáčová, Martina, Humajová, Jana, Tomšík, Pavel, and Gasser, Gilles

Abstract

Chemotherapy remains one of the dominant treatments to cure cancer. However, due to the many inherent drawbacks, there is a search for new chemotherapeutic drugs. Many classes of compounds have been investigated over the years to discover new targets and synergistic mechanisms of action including multicellular targets. In this work, we designed a new chemotherapeutic drug candidate against cancer, namely, [Ru(DIP)2(sq)](PF6)(Ru-sq) (DIP = 4,7-diphenyl-1,10-phenanthroline; sq = semiquinonate ligand). The aim was to combine the great potential expressed by Ru(II) polypyridyl complexes and the singular redox and biological properties associated with the catecholate moiety. Experimental evidence (e.g., X-ray crystallography, electron paramagnetic resonance, electrochemistry) demonstrates that the semiquinonate is the preferred oxidation state of the dioxo ligand in this complex. The biological activity of Ru-sqwas then scrutinized in vitroand in vivo, and the results highlight the promising potential of this complex as a chemotherapeutic agent against cancer.

Published
2020
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30. Mechanisms of action of Ru(ii) polypyridyl complexes in living cells upon light irradiation.

Author

Gasser, Gilles, Jakubaszek, Marta, Goud, Bruno, and Ferrari, Stefano

Subjects
*RUTHENIUM compounds, *PHOTODYNAMIC therapy, *IRRADIATION
Abstract

The unique photophysical properties of Ru(ii) polypyridyl complexes make them very attractive candidates as photosensitisers in Photodynamic Therapy (PDT). However, to date, there are not many studies exploring in detail the mechanism(s) of action of such compounds in living systems upon light irradiation. This feature article provides an overview of the most in-depth biological studies on such compounds. [ABSTRACT FROM AUTHOR]

Published
2018
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31. Evaluation of the potential of cobalamin derivatives bearing ru(ii) polypyridyl complexes as photosensitizers for photodynamic therapy

Author

Jakubaszek, Marta, Rossier, Jeremie, Karges, Johannes, Delasoie, Joachim, Goud, Bruno, Gasser, Gilles, Zobi, Fabio, Jakubaszek, Marta, Rossier, Jeremie, Karges, Johannes, Delasoie, Joachim, Goud, Bruno, Gasser, Gilles, and Zobi, Fabio

Abstract

The current photosensitizers (PSs) for photodynamic therapy (PDT) lack selectivity for cancer cells. To tackle this drawback, in view of selective cancer delivery, we envisioned conjugating two ruthenium polypyridyl complexes to vitamin B12 (Cobalamin, Cbl) to take advantage of the solubility and active uptake of the latter. Ultimately, our results showed that the transcobalamin pathway is unlikely involved for the delivery of these ruthenium‐based PDT PSs, emphasizing the difficulty in successfully delivering metal complexes to cancer cells.

32. Three in One: In Vitro and In Vivo Evaluation of Anticancer Activity of a Theranostic Agent that Combines Magnetic Resonance Imaging, Optical Bioimaging, and Photodynamic Therapy Capabilities.

Author

Boumati S, Sour A, Heitz V, Seguin J, Beitz G, Kaga Y, Jakubaszek M, Karges J, Gasser G, Mignet N, and Doan BT

Subjects
Humans, Precision Medicine, Tissue Distribution, Magnetic Resonance Imaging, Photochemotherapy methods, Neoplasms diagnostic imaging, Neoplasms drug therapy
Abstract

Cancer treatment is a crucial area of research and development, as current chemotherapeutic treatments can have severe side effects or poor outcomes. In the constant search for new strategies that are localized and minimally invasive and produce minimal side effects, photodynamic therapy (PDT) is an exciting therapeutic modality that has been gaining attention. The use of theranostics, which combine diagnostic and therapeutic capabilities, can further improve treatment monitoring through image guidance. This study explores the potential of a theranostic agent consisting of four Gd(III) DTTA complexes (DTTA: diethylenetriamine- N , N , N ″, N ″-tetraacetate) grafted to a meso- tetraphenylporphyrin core for PDT, fluorescence, and magnetic resonance imaging (MRI). The agent was first tested in vitro on both nonmalignant TIB-75 and MRC-5 and tumoral CT26 and HT-29 cell lines and subsequently evaluated in vivo in a preclinical colorectal tumor model. Advanced MRI and optical imaging techniques were employed with engineered quantitative in vivo molecular imaging based on dynamic acquisition sequences to track the biodistribution of agents in the body. With 3D quantitative volume computed by MRI and tumoral cell function assessed by bioluminescence imaging, we could demonstrate a significant impact of the molecular agent on tumor growth following light application. Further exhaustive histological analysis confirmed these promising results, making this theranostic agent a potential drug candidate for cancer.

Published
2023
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33. Synthesis and Characterization of an Epidermal Growth Factor Receptor-Selective Ru II Polypyridyl-Nanobody Conjugate as a Photosensitizer for Photodynamic Therapy.

Author

Karges J, Jakubaszek M, Mari C, Zarschler K, Goud B, Stephan H, and Gasser G

Subjects
Cell Line, Tumor, ErbB Receptors antagonists & inhibitors, Humans, Neoplasms drug therapy, Organometallic Compounds chemical synthesis, Organometallic Compounds chemistry, Photochemotherapy, Photosensitizing Agents chemical synthesis, Photosensitizing Agents chemistry, Polycyclic Compounds chemical synthesis, Polycyclic Compounds chemistry, Ruthenium chemistry
Abstract

There is a current surge of interest in the development of novel photosensitizers (PSs) for photodynamic therapy (PDT), as those currently approved are not completely ideal. Among the tested compounds, we have previously investigated the use of Ru II polypyridyl complexes with a [Ru(bipy) 2 (dppz)] 2+ and [Ru(phen) 2 (dppz)] 2+ scaffold (bipy=2,2'-bipyridine; dppz=dipyrido[3,2-a:2',3'-c]phenazine; phen=1,10-phenanthroline). These complexes selectively target DNA. However, because DNA is ubiquitous, it would be of great interest to increase the selectivity of our PDT PSs by linking them to a targeting vector in view of targeted PDT. Herein, we present the synthesis, characterization, and in-depth photophysical evaluation of a nanobody-containing Ru II polypyridyl conjugate selective for the epidermal growth factor receptor (EGFR) in view of targeted PDT. Using ICP-MS and confocal microscopy, we could demonstrate that our conjugate has high selectivity for the EGFR receptor, which is a crucial oncological target because it is overexpressed and/or deregulated in a variety of solid tumors. However, in contrast to expectations, this conjugate was found to not produce reactive oxygen species (ROS) in cancer cells and is therefore not phototoxic., (© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)

Published
2020
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