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Novel Functional Hydroxypyridinone-Based Derivatives
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Novel Functional Hydroxypyridinone-Based Derivatives

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (30 April 2022) | Viewed by 17316

Special Issue Editors

Prof. Dr. M. Amelia Santos

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Guest Editor
Centro de Química Estrutural and Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal
Interests: medicinal and enviromnmental chemistry; development and evaluation of polyfunctional chelating compounds for metal decorporation; metal modulation by multitarget drugs to combat neurodegenerative diseases
Special Issues, Collections and Topics in MDPI journals
Dr. Sílvia Chaves

E-Mail Website1 Website2
Guest Editor
Centro de Química Estrutural, Institute of Molecular Sciences, Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal
Interests: chelating agents; anti-neurodegeneratives; molecular modelling; bioinorganic chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Hydroxypyridinones, a family of N-heterocyclic metal chelators, have a quite attractive structure for drug design. In fact, they possess a high metal chelating efficacy, low toxicity and are easy to derivatize in order to improve bioavailability and interaction with specific biological sites. The interest in these types of compounds started with the disclosure of deferiprone, a 3-hydroxy-4-pyridinone compound, which is still in clinical use for the therapy of iron overload/dyshomeostasis associated with certain diseases. More than three decades of research in this area has revealed a variety of applications for the hydroxypyridinone-based compounds such as anti-microbial/biostatic agents, anti-cancer, anti-Alzheimer´s disease multi-target drugs, inhibitors of metalloenzymes, luminescent biosensors, phototherapeutic drugs or diagnostic agents.

We are now launching a Special Issue on "Novel Functional Hydroxypyridinone-

Based Derivatives" for publication in Molecules, an open access journal of the Swiss MDPI editorial. In this Special Issue, original research articles and reviews devoted to the development and study of hydroxypyridinone-based compounds, either extra functionalized bidentate chelators or polydentate derivatives, as well as macromolecular or nanomolecular chelators as carriers of tailored drugs, are welcome.

Prof. Dr. M. Amelia Santos
Prof. Dr. Sílvia Chaves
Guest Editors

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Keywords

  • Metals in diseases
  • Metal decorporation agents
  • Hydroxypyridinones
  • Polyfunctional ligands
  • Anti-neurodegenerative chelating drugs
  • 3,4-Hydroxypyridinones
  • Metal sensors

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Published Papers (6 papers)

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Research

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13 pages, 3548 KiB  
Article
Pd(II) Binding Strength of a Novel Ambidentate Dipeptide-Hydroxypyridinonate Ligand: A Solution Equilibrium Study
by Linda Bíró, András Ozsváth, Réka Kapitány and Péter Buglyó
Molecules 2022, 27(14), 4667; https://doi.org/10.3390/molecules27144667 - 21 Jul 2022
Viewed by 1548
Abstract
A novel ambidentate dipeptide conjugate (H(L1)) containing N-donor atoms of the peptide part and an (O,O) chelate at the hydroxypyridinone (HP) ring is synthesized and characterized. It is hoped that this chelating ligand can be useful to obtain multitargeted Co(III)/Pt(II) dinuclear complexes with [...] Read more.
A novel ambidentate dipeptide conjugate (H(L1)) containing N-donor atoms of the peptide part and an (O,O) chelate at the hydroxypyridinone (HP) ring is synthesized and characterized. It is hoped that this chelating ligand can be useful to obtain multitargeted Co(III)/Pt(II) dinuclear complexes with anticancer potential. The Pd(II) (as a Pt(II) model but with faster ligand exchange reactions) binding strength of the ligand was studied in an aqueous solution with the combined use of pH-potentiometry and NMR. In an equimolar solution, (L1)− was found to bind Pd(II) via the terminal amino and increasing number of peptide nitrogens of the peptide backbone over a wide pH range. At a 2:1 Pd(II) to ligand ratio, the presence of [Pd2H–x(L1)] (x = 1–4) species, with high stability and with the coordination of the (O,O) chelating set of the ligand, was detected. The reaction of H(L1) with [Co(tren)]3+ (tren = tris(2-aminoethyl)amine) indicated the exclusive binding of (L1)− via its (O,O) donor atoms to the metal unit, while treatment of the resulting Co-complex with Pd(II) afforded the formation of a Co/Pd heterobimetallic complex in solution with an (NH2, Namide) coordination of Pd(II). Shortening the peptide backbone in H(L1) by one peptide unit compared to the structurally similar ambidentate chelator consisting of three peptide bonds resulted in the slightly more favorable formation of the N-coordinated Pd(II) species, allowing the tailoring of the coordination properties. Full article
(This article belongs to the Special Issue Novel Functional Hydroxypyridinone-Based Derivatives)
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19 pages, 3759 KiB  
Article
1-Hydroxy-2(1H)-pyridinone-Based Chelators with Potential Catechol O-Methyl Transferase Inhibition and Neurorescue Dual Action against Parkinson’s Disease
by Joseph C. J. Bergin, Kean Kan Tan, Anya K. Nelson, Cristina-Andreea Amarandei, Véronique Hubscher-Bruder, Jérémy Brandel, Varvara Voinarovska, Annick Dejaegere, Roland H. Stote and David Tétard
Molecules 2022, 27(9), 2816; https://doi.org/10.3390/molecules27092816 - 28 Apr 2022
Cited by 1 | Viewed by 2476
Abstract
Two analogues of tolcapone where the nitrocatechol group has been replaced by a 1-hydroxy-2(1H)-pyridinone have been designed and synthesised. These compounds are expected to have a dual mode of action both beneficial against Parkinson’s disease: they are designed to be inhibitors [...] Read more.
Two analogues of tolcapone where the nitrocatechol group has been replaced by a 1-hydroxy-2(1H)-pyridinone have been designed and synthesised. These compounds are expected to have a dual mode of action both beneficial against Parkinson’s disease: they are designed to be inhibitors of catechol O-methyl transferase, which contribute to the reduction of dopamine in the brain, and to protect neurons against oxidative damage. To assess whether these compounds are worthy of biological assessment to demonstrate these effects, measurement of their pKa and stability constants for Fe(III), in silico modelling of their potential to inhibit COMT and blood–brain barrier scoring were performed. These results demonstrate that the compounds may indeed have the desired properties, indicating they are indeed promising candidates for further evaluation. Full article
(This article belongs to the Special Issue Novel Functional Hydroxypyridinone-Based Derivatives)
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14 pages, 1493 KiB  
Article
Functionalization of Rhodamine Platforms with 3-Hydroxy-4-pyridinone Chelating Units and Its Fluorescence Behavior towards Fe(III)
by Carla Queirós, Sílvia Vinhas, Jéssica Oliveira, Andreia Leite, Ana M. G. Silva and Maria Rangel
Molecules 2022, 27(5), 1567; https://doi.org/10.3390/molecules27051567 - 26 Feb 2022
Viewed by 2616
Abstract
Functionalization of xanthene fluorophores with specific receptor units is an important topic of research aiming for the development of new analytical tools for biological sciences, clinical diagnosis, food and environmental monitoring. Herein, we report a new dihydrorosamine containing two active amino groups, which [...] Read more.
Functionalization of xanthene fluorophores with specific receptor units is an important topic of research aiming for the development of new analytical tools for biological sciences, clinical diagnosis, food and environmental monitoring. Herein, we report a new dihydrorosamine containing two active amino groups, which was functionalized with 3-benzyloxy-1-(3′-carboxypropyl)-2-methyl-4-pyridinone through an amide coupling strategy. Benzylated mono- and di-functionalized dihydrorosamine derivatives (H in position 9 of the xanthene) were obtained, but with modest reaction yields, requiring long and laborious purification procedures. Looking for a more efficient approach, rhodamine 110 was selected to react with the carboxypropyl pyridinone, enabling the isolation of the corresponding mono- and di-functionalized derivatives in amounts that depend on the excess of pyridinone added to the reaction. The structure of all compounds was established by 1H and 13C NMR, MS (ESI) and their absorption and emission properties were evaluated in dichloromethane. The fluorescence behavior of the debenzylated mono-rhodamine 110 derivative in the presence of Fe(III) was studied, making it an interesting fluorogenic dye for future optical sensing applications. Full article
(This article belongs to the Special Issue Novel Functional Hydroxypyridinone-Based Derivatives)
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11 pages, 2936 KiB  
Article
A Multi-Technique Investigation of the Complex Formation Equilibria between Bis-Deferiprone Derivatives and Oxidovanadium (IV)
by Rosita Cappai, Alessandra Fantasia, Guido Crisponi, Eugenio Garribba, M. Amélia Santos and Valeria Marina Nurchi
Molecules 2022, 27(5), 1555; https://doi.org/10.3390/molecules27051555 - 25 Feb 2022
Cited by 3 | Viewed by 1620
Abstract
The increasing biomedical interest in high-stability oxidovanadium(IV) complexes with hydroxypyridinone ligands leads us to investigate the complex formation equilibria of VIVO2+ ion with a tetradentate ligand, named KC21, which contains two 3-hydroxy-1,2-dimethylpyridin-4(1H)-one (deferiprone) moieties, and with the simple [...] Read more.
The increasing biomedical interest in high-stability oxidovanadium(IV) complexes with hydroxypyridinone ligands leads us to investigate the complex formation equilibria of VIVO2+ ion with a tetradentate ligand, named KC21, which contains two 3-hydroxy-1,2-dimethylpyridin-4(1H)-one (deferiprone) moieties, and with the simple bidentate ligand that constitutes the basic unit of KC21, for comparison, named L5. These equilibrium studies were conducted with joined potentiometric–spectrophotometric titrations, and the results were substantiated with EPR measurements at variable pH values. This multi-technique study gave evidence of the formation of an extremely stable 1:1 complex between KC21 and oxidovanadium(IV) at a physiological pH, which could find promising pharmacological applications. Full article
(This article belongs to the Special Issue Novel Functional Hydroxypyridinone-Based Derivatives)
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Review

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26 pages, 1712 KiB  
Review
Hydroxypyridinone-Based Metal Chelators towards Ecotoxicity: Remediation and Biological Mechanisms
by M. Amélia Santos, Anna Irto, Péter Buglyó and Sílvia Chaves
Molecules 2022, 27(6), 1966; https://doi.org/10.3390/molecules27061966 - 18 Mar 2022
Cited by 5 | Viewed by 3688
Abstract
Hydroxypyridinones (HPs) are recognized as excellent chemical tools for engineering a diversity of metal chelating agents, with high affinity for hard metal ions, exhibiting a broad range of activities and applications, namely in medical, biological and environmental contexts. They are easily made and [...] Read more.
Hydroxypyridinones (HPs) are recognized as excellent chemical tools for engineering a diversity of metal chelating agents, with high affinity for hard metal ions, exhibiting a broad range of activities and applications, namely in medical, biological and environmental contexts. They are easily made and functionalizable towards the tuning of their pharmacokinetic properties or the improving of their metal complex thermodynamic stabilities. In this review, an analysis of the recently published works on hydroxypyridinone-based ligands, that have been mostly addressed for environmental applications, namely for remediation of hard metal ion ecotoxicity in living beings and other biological matrices is carried out. In particular, herein the most recent developments in the design of new chelating systems, from bidentate mono-HP to polydentate multi-HP derivatives, with a structural diversity of soluble or solid-supported backbones are outlined. Along with the ligand design, an analysis of the relationship between their structures and activities is presented and discussed, namely associated with the metal affinity and the thermodynamic stability of the corresponding metal complexes. Full article
(This article belongs to the Special Issue Novel Functional Hydroxypyridinone-Based Derivatives)
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34 pages, 3497 KiB  
Review
Hydroxypyridinones as a Very Promising Platform for Targeted Diagnostic and Therapeutic Radiopharmaceuticals
by Xu Zhou, Linlin Dong and Langtao Shen
Molecules 2021, 26(22), 6997; https://doi.org/10.3390/molecules26226997 - 19 Nov 2021
Cited by 9 | Viewed by 4407
Abstract
Hydroxypyridinones (HOPOs) have been used in the chelation therapy of iron and actinide metals. Their application in metal-based radiopharmaceuticals has also been increasing in recent years. This review article focuses on how multidentate HOPOs can be used in targeted radiometal-based diagnostic and therapeutic [...] Read more.
Hydroxypyridinones (HOPOs) have been used in the chelation therapy of iron and actinide metals. Their application in metal-based radiopharmaceuticals has also been increasing in recent years. This review article focuses on how multidentate HOPOs can be used in targeted radiometal-based diagnostic and therapeutic radiopharmaceuticals. The general structure of radiometal-based targeted radiopharmaceuticals, a brief description of siderophores, the basic structure and properties of bidentate HOPO, some representative HOPO multidentate chelating agents, radiopharmaceuticals based on HOPO multidentate bifunctional chelators for gallium-68, thorium-227 and zirconium-89, as well as the future prospects of HOPO multidentate bifunctional chelators in other metal-based radiopharmaceuticals are described and discussed in turn. The HOPO metal-based radiopharmaceuticals that have shown good prospects in clinical and preclinical studies are gallium-68, thorium-227 and zirconium-89 radiopharmaceuticals. We expect HOPO multidentate bifunctional chelators to be a very promising platform for building novel targeted radiometal-based diagnostic and therapeutic radiopharmaceuticals. Full article
(This article belongs to the Special Issue Novel Functional Hydroxypyridinone-Based Derivatives)
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