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Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry

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

Deadline for manuscript submissions: closed (31 December 2020) | Viewed by 41672

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Dr. Maria Emília De Sousa

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1. Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), 4450-208 Porto, Portugal
2. Laboratory of Organic and Pharmaceutical Chemistry, Faculty of Pharmacy, University of Porto, 4050-313 Porto, Portugal
Interests: medicinal chemistry; organic synthesis; heterocycles; P-glycoprotein; anticancer; antimicrobials; chiral drugs; marine natural products
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Prof. Dr. Katalin Prokai-Tatrai

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Department of Pharmacology and Neuroscience, University of North Texas Health Science Center, Fort Worth, TX 76107, USA
Interests: drug design of central nervous system agents; neuropeptides and peptidomimetics; prodrugs for CNS delivery; CNS-selective estrogen therapy; neuroprotection; proteomics
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Dr. Paula A. C. Gomes

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LAQV-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Porto, Portugal
Interests: anti-infective agents; antimicrobial peptides; antiparasitic drugs; drug rescuing and repurposing; peptide-grafted materials; peptide synthesis
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Prof. Dr. Stefania Galdiero

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Department of Pharmacy, University of Naples Federico II, Via Mezzocannone 16, 80134 Napoli, Italy
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Prof. Dr. Sandra Gemma

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Department of Biotechnology, Chemistry and Pharmacy, University of Siena, Via Aldo Moro 2, 53100 Siena, Italy
Interests: medicinal chemistry; small molecules; drug discovery; structure-activity relationships; anti-infective agents; parasitic diseases; chemotherapeutics; synthesis of biologically active compounds
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Prof. Dr. Mariana Spetea

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Institute of Pharmacy, Department of Pharmaceutical Chemistry, Center for Molecular Biosciences (CMBI), University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria
Interests: opioid receptors; opioid pharmacology; pain research; CNS disorders; opioid drug discovery; structure-activity-relationships; GPCRs signalling
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Prof. Dr. Anne Roivainen

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1. Turku PET Centre, University of Turku, Turku, Finland
2. Turku Center for Disease Modeling, University of Turku, Turku, Finland
3. Turku PET Centre, Turku University Hospital, Turku, Finland
Interests: medical biochemistry; radiopharmaceuticals; molecular imaging; imaging agents; inflammation; infection; cancer
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Special Issue Information

Dear Colleagues,

To emphasize women's contributions to the field of medicinal chemistry, our journal, Molecules, will launch a Special Issue on “Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry” to be published in Molecules (ISSN 1420-3049, https://www.mdpi.com/journal/molecules) in 2020. This Special Issue will include high-quality papers and review articles in all areas of medicinal chemistry. We invite medicinal chemists from around the world to share their original research led by female scientist(s) or contribute with up-to-date reviews highlighting the leading role of women in the advancement of the field.

Prof. Maria Emília de Sousa
Prof. Dr. Katalin Prokai-Tatrai
Prof. Dr. Paula A. C. Gomes
Prof. Stefania Galdiero
Prof. Dr. Sandra Gemma
Prof. Dr. Mariana Spetea
Prof. Anne Roivainen
Guest Editors

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Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

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Published Papers (10 papers)

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Research

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19 pages, 1556 KiB

Open AccessFeature PaperArticle

Antinociceptive Efficacy of the µ-Opioid/Nociceptin Peptide-Based Hybrid KGNOP1 in Inflammatory Pain without Rewarding Effects in Mice: An Experimental Assessment and Molecular Docking

by Maria Dumitrascuta, Marcel Bermudez, Olga Trovato, Jolien De Neve, Steven Ballet, Gerhard Wolber and Mariana Spetea

Molecules 2021, 26(11), 3267; https://doi.org/10.3390/molecules26113267 - 28 May 2021

Cited by 11 | Viewed by 3168

Abstract

Opioids are the most effective analgesics, with most clinically available opioids being agonists to the µ-opioid receptor (MOR). The MOR is also responsible for their unwanted effects, including reward and opioid misuse leading to the current public health crisis. The imperative need for safer, non-addictive pain therapies drives the search for novel leads and new treatment strategies. In this study, the recently discovered MOR/nociceptin (NOP) receptor peptide hybrid KGNOP1 (H-Dmt-D-Arg-Aba-β-Ala-Arg-Tyr-Tyr-Arg-Ile-Lys-NH₂) was evaluated following subcutaneous administration in mouse models of acute (formalin test) and chronic inflammatory pain (Complete Freund’s adjuvant-induced paw hyperalgesia), liabilities of spontaneous locomotion, conditioned place preference, and the withdrawal syndrome. KGNOP1 demonstrated dose-dependent antinociceptive effects in the formalin test, and efficacy in attenuating thermal hyperalgesia with prolonged duration of action. Antinociceptive effects of KGNOP1 were reversed by naltrexone and SB-612111, indicating the involvement of both MOR and NOP receptor agonism. In comparison with morphine, KGNOP1 was more potent and effective in mouse models of inflammatory pain. Unlike morphine, KGNOP1 displayed reduced detrimental liabilities, as no locomotor impairment nor rewarding and withdrawal effects were observed. Docking of KGNOP1 to the MOR and NOP receptors and subsequent 3D interaction pattern analyses provided valuable insights into its binding mode. The mixed MOR/NOP receptor peptide KGNOP1 holds promise in the effort to develop new analgesics for the treatment of various pain states with fewer MOR-mediated side effects, particularly abuse and dependence liabilities. Full article

(This article belongs to the Special Issue Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry)

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13 pages, 22419 KiB

Open AccessArticle

Covalent Histone Modification by an Electrophilic Derivative of the Anti-HIV Drug Nevirapine

by Shrika G. Harjivan, Catarina Charneira, Inês L. Martins, Sofia A. Pereira, Guadalupe Espadas, Eduard Sabidó, Frederick A. Beland, M. Matilde Marques and Alexandra M. M. Antunes

Molecules 2021, 26(5), 1349; https://doi.org/10.3390/molecules26051349 - 3 Mar 2021

Cited by 5 | Viewed by 2785

Abstract

Nevirapine (NVP), a non-nucleoside reverse transcriptase inhibitor widely used in combined antiretroviral therapy and to prevent mother-to-child transmission of the human immunodeficiency virus type 1, is associated with several adverse side effects. Using 12-mesyloxy-nevirapine, a model electrophile of the reactive metabolites derived from the NVP Phase I metabolite, 12-hydroxy-NVP, we demonstrate that the nucleophilic core and C-terminal residues of histones are targets for covalent adduct formation. We identified multiple NVP-modification sites at lysine (e.g., H2BK47, H4K32), histidine (e.g., H2BH110, H4H76), and serine (e.g., H2BS33) residues of the four histones using a mass spectrometry-based bottom-up proteomic analysis. In particular, H2BK47, H2BH110, H2AH83, and H4H76 were found to be potential hot spots for NVP incorporation. Notably, a remarkable selectivity to the imidazole ring of histidine was observed, with modification by NVP detected in three out of the 11 histidine residues of histones. This suggests that NVP-modified histidine residues of histones are prospective markers of the drug’s bioactivation and/or toxicity. Importantly, NVP-derived modifications were identified at sites known to determine chromatin structure (e.g., H4H76) or that can undergo multiple types of post-translational modifications (e.g., H2BK47, H4H76). These results open new insights into the molecular mechanisms of drug-induced adverse reactions. Full article

(This article belongs to the Special Issue Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry)

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22 pages, 17115 KiB

Open AccessArticle

From Combinations to Single-Molecule Polypharmacology—Cromolyn-Ibuprofen Conjugates for Alzheimer’s Disease

by Claudia Albertini, Marina Naldi, Sabrina Petralla, Silvia Strocchi, Daniela Grifoni, Barbara Monti, Manuela Bartolini and Maria Laura Bolognesi

Molecules 2021, 26(4), 1112; https://doi.org/10.3390/molecules26041112 - 19 Feb 2021

Cited by 7 | Viewed by 3865

Abstract

Despite Alzheimer’s disease (AD) incidence being projected to increase worldwide, the drugs currently on the market can only mitigate symptoms. Considering the failures of the classical paradigm “one target-one drug-one disease” in delivering effective medications for AD, polypharmacology appears to be a most viable therapeutic strategy. Polypharmacology can involve combinations of multiple drugs and/or single chemical entities modulating multiple targets. Taking inspiration from an ongoing clinical trial, this work aims to convert a promising cromolyn–ibuprofen drug combination into single-molecule “codrugs.” Such codrugs should be able to similarly modulate neuroinflammatory and amyloid pathways, while showing peculiar pros and cons. By exploiting a linking strategy, we designed and synthesized a small set of cromolyn–ibuprofen conjugates (4–6). Preliminary plasma stability and neurotoxicity assays allowed us to select diamide 5 and ethanolamide 6 as promising compounds for further studies. We investigated their immunomodulatory profile in immortalized microglia cells, in vitro anti-aggregating activity towards Aβ₄₂-amyloid self-aggregation, and their cellular neuroprotective effect against Aβ₄₂-induced neurotoxicity. The fact that 6 effectively reduced Aβ-induced neuronal death, prompted its investigation into an in vivo model. Notably, 6 was demonstrated to significantly increase the longevity of Aβ₄₂-expressing Drosophila and to improve fly locomotor performance. Full article

(This article belongs to the Special Issue Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry)

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16 pages, 3086 KiB

Open AccessFeature PaperArticle

New Antineoplastic Naphthohydroquinones Attached to Labdane and Rearranged Diterpene Skeletons

by Ángela P. Hernández, Pablo Chamorro, Mª Lucena Rodríguez, José M. Miguel del Corral, Pablo A. García, Andrés Francesch, Arturo San Feliciano and Mª Ángeles Castro

Molecules 2021, 26(2), 474; https://doi.org/10.3390/molecules26020474 - 18 Jan 2021

Cited by 3 | Viewed by 1982

Abstract

Terpenylquinones are mixed biogenesis primary or secondary metabolites widespread in Nature with many biological activities, including the antineoplastic cytotoxicity, that have inspired this work. Here, we present a cytotoxic structure-activity relationship of several diterpenylhydroquinone (DTHQ) derivatives, obtained from the natural labdane diterpenoid myrceocommunic acid used as starting material. Different structural modifications, that changed the functionality and stereochemistry of the decalin, have been implemented on the bicyclic core through epoxidation, ozonolysis or decarboxylation, and through induction of biomimetic breaks and rearrangements of the diterpene skeleton. All the isomers generated were completely characterized by spectroscopic procedures. The resulting compounds have been tested in vitro on cultured cancer cells, showing their relevant antineoplastic cytotoxicity, with GI₅₀ values in the μM and sub-μM range. The rearranged compound 8 showed the best cytotoxic results, with GI₅₀ at the submicromolar range, retaining the cytotoxicity level of the parent compounds. In this report, the versatility of the labdane skeleton for chemical transformation and the interest to continue using structural modifications to obtain new bioactive compounds are demonstrated. Full article

(This article belongs to the Special Issue Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry)

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28 pages, 2659 KiB

Open AccessArticle

Hybridization of Curcumin Analogues with Cinnamic Acid Derivatives as Multi-Target Agents Against Alzheimer’s Disease Targets

by Eirini Chainoglou, Argyris Siskos, Eleni Pontiki and Dimitra Hadjipavlou-Litina

Molecules 2020, 25(21), 4958; https://doi.org/10.3390/molecules25214958 - 26 Oct 2020

Cited by 16 | Viewed by 4302

Abstract

The synthesis of the new hybrids followed a hybridization with the aid of hydroxy-benzotriazole (HOBT) and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI.HCL) in dry DMF or thionyl chloride between curcumin analogues and cinnamic acid derivatives. IR, ¹H-NMR, ¹³C-NMR, LC/MS ESI⁺, and elemental analysis were used for the confirmation of the structures of the novel hybrids. The lipophilicity values of compounds were calculated theoretically and experimentally via the reversed chromatography method as R_M values. The novel derivatives were studied through in vitro experiments for their activity as antioxidant agents and as inhibitors of lipoxygenase, cyclooxygenase-2, and acetyl-cholinesterase. All the compounds showed satisfying anti-lipid peroxidation activity of linoleic acid induced by 2,2′-azobis(2-amidinopropane) hydrochloride (AAPH). Hybrid 3e was the most significant pleiotropic derivative, followed by 3a. According to the predicted results, all hybrids could be easily transported, diffused, and absorbed through the blood–brain barrier (BBB). They presented good oral bioavailability and very high absorption with the exception of 3h. No inhibition for CYP1A2, CYP2C9, CYP2C19, CYP2D6, and CYP3A4 was noticed. According to the Ames test, all the hybrids induced mutagenicity with the exception of 3d. Efforts were conducted a) to correlate the in vitro results with the most important physicochemical properties of the structural components of the molecules and b) to clarify the correlation of actions among them to propose a possible mechanism of action. Docking studies were performed on soybean lipoxygenase (LOX) and showed hydrophobic interactions with amino acids. Docking studies on acetylcholinesterase (AChE) exhibited: (a) hydrophobic interactions with TRP281, LEU282, TYR332, PHE333, and TYR336 and (b) π-stacking interactions with TYR336. Full article

(This article belongs to the Special Issue Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry)

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15 pages, 2907 KiB

Open AccessArticle

Design, Synthesis and Functional Analysis of Cyclic Opioid Peptides with Dmt-Tic Pharmacophore

by Arijit Sarkar, Anna Adamska-Bartlomiejczyk, Justyna Piekielna-Ciesielska, Karol Wtorek, Alicja Kluczyk, Attila Borics and Anna Janecka

Molecules 2020, 25(18), 4260; https://doi.org/10.3390/molecules25184260 - 17 Sep 2020

Cited by 2 | Viewed by 3216

Abstract

The opioid receptors are members of the G-protein-coupled receptor (GPCR) family and are known to modulate a variety of biological functions, including pain perception. Despite considerable advances, the mechanisms by which opioid agonists and antagonists interact with their receptors and exert their effect are still not completely understood. In this report, six new hybrids of the Dmt-Tic pharmacophore and cyclic peptides, which were shown before to have a high affinity for the µ-opioid receptor (MOR) were synthesized and characterized pharmacologically in calcium mobilization functional assays. All obtained ligands turned out to be selective antagonists of the δ-opioid receptor (DOR) and did not activate or block the MOR. The three-dimensional structural determinants responsible for the DOR antagonist properties of these analogs were further investigated by docking studies. The results indicate that these compounds attach to the DOR in a slightly different orientation with respect to the Dmt-Tic pharmacophore than Dmt-TicΨ[CH₂-NH]Phe-Phe-NH₂ (DIPP-NH₂[Ψ]), a prototypical DOR antagonist peptide. Key pharmacophoric contacts between the DOR and the ligands were maintained through an analogous spatial arrangement of pharmacophores, which could provide an explanation for the predicted high-affinity binding and the experimentally observed functional properties of the novel synthetic ligands. Full article

(This article belongs to the Special Issue Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry)

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Review

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18 pages, 8708 KiB

Open AccessReview

Acridine-Based Antimalarials—From the Very First Synthetic Antimalarial to Recent Developments

by Mélanie Fonte, Natália Tassi, Paula Gomes and Cátia Teixeira

Molecules 2021, 26(3), 600; https://doi.org/10.3390/molecules26030600 - 24 Jan 2021

Cited by 25 | Viewed by 4028

Abstract

Malaria is among the deadliest infectious diseases in the world caused by Plasmodium parasites. Due to the high complexity of the parasite’s life cycle, we partly depend on antimalarial drugs to fight this disease. However, the emergence of resistance, mainly by Plasmodium falciparum, has dethroned most of the antimalarials developed to date. Given recent reports of resistance to artemisinin combination therapies, first-line treatment currently recommended by the World Health Organization, in Western Cambodia and across the Greater Mekong sub-region, it seems very likely that artemisinin and its derivatives will follow the same path of other antimalarial drugs. Consequently, novel, safe and efficient antimalarial drugs are urgently needed. One fast and low-cost strategy to accelerate antimalarial development is by recycling classical pharmacophores. Quinacrine, an acridine-based compound and the first clinically tested synthetic antimalarial drug with potent blood schizonticide but serious side effects, has attracted attention due to its broad spectrum of biological activity. In this sense, the present review will focus on efforts made in the last 20 years for the development of more efficient, safer and affordable antimalarial compounds, through recycling the classical quinacrine drug. Full article

(This article belongs to the Special Issue Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry)

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19 pages, 1386 KiB

Open AccessFeature PaperReview

Modulating Protein–Protein Interactions by Cyclic and Macrocyclic Peptides. Prominent Strategies and Examples

by Rosario González-Muñiz, María Ángeles Bonache and María Jesús Pérez de Vega

Molecules 2021, 26(2), 445; https://doi.org/10.3390/molecules26020445 - 16 Jan 2021

Cited by 20 | Viewed by 4762

Abstract

Cyclic and macrocyclic peptides constitute advanced molecules for modulating protein–protein interactions (PPIs). Although still peptide derivatives, they are metabolically more stable than linear counterparts, and should have a lower degree of flexibility, with more defined secondary structure conformations that can be adapted to imitate protein interfaces. In this review, we analyze recent progress on the main methods to access cyclic/macrocyclic peptide derivatives, with emphasis in a few selected examples designed to interfere within PPIs. These types of peptides can be from natural origin, or prepared by biochemical or synthetic methodologies, and their design could be aided by computational approaches. Some advances to facilitate the permeability of these quite big molecules by conjugation with cell penetrating peptides, and the incorporation of β-amino acid and peptoid structures to improve metabolic stability, are also commented. It is predicted that this field of research could have an important future mission, running in parallel to the discovery of new, relevant PPIs involved in pathological processes. Full article

(This article belongs to the Special Issue Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry)

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43 pages, 7486 KiB

Open AccessReview

From Natural Products to New Synthetic Small Molecules: A Journey through the World of Xanthones

by Madalena M. M. Pinto, Andreia Palmeira, Carla Fernandes, Diana I. S. P. Resende, Emília Sousa, Honorina Cidade, Maria Elizabeth Tiritan, Marta Correia-da-Silva and Sara Cravo

Molecules 2021, 26(2), 431; https://doi.org/10.3390/molecules26020431 - 15 Jan 2021

Cited by 63 | Viewed by 7299

Abstract

This work reviews the contributions of the corresponding author (M.M.M.P.) and her research group to Medicinal Chemistry concerning the isolation from plant and marine sources of xanthone derivatives as well as their synthesis, biological/pharmacological activities, formulation and analytical applications. Although her group activity has been spread over several chemical families with relevance in Medicinal Chemistry, the main focus of the investigation and research has been in the xanthone family. Xanthone derivatives have a variety of activities with great potential for therapeutic applications due to their versatile framework. The group has contributed with several libraries of xanthones derivatives, with a variety of activities such as antitumor, anticoagulant, antiplatelet, anti-inflammatory, antimalarial, antimicrobial, hepatoprotective, antioxidant, and multidrug resistance reversal effects. Besides therapeutic applications, our group has also developed xanthone derivatives with analytical applications as chiral selectors for liquid chromatography and for maritime application as antifouling agents for marine paints. Chemically, it has been challenging to afford green chemistry methods and achieve enantiomeric purity of chiral derivatives. In this review, the structures of the most significant compounds will be presented. Full article

(This article belongs to the Special Issue Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry)

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17 pages, 1862 KiB

Open AccessReview

Nucleophilic Synthesis of 6-l-[¹⁸F]FDOPA. Is Copper-Mediated Radiofluorination the Answer?

by Raisa N. Krasikova

Molecules 2020, 25(19), 4365; https://doi.org/10.3390/molecules25194365 - 23 Sep 2020

Cited by 13 | Viewed by 4411

Abstract

Positron emission tomography employing 6-l-[¹⁸F]fluoro-3,4-dihydroxyphenylalanine (6-l-[¹⁸F]FDOPA) is currently a highly relevant clinical tool for detection of gliomas, neuroendocrine tumors and evaluation of Parkinson’s disease progression. Yet, the deficiencies of electrophilic synthesis of 6-l-[¹⁸F]FDOPA hold back its wider use. To fulfill growing clinical demands for this radiotracer, novel synthetic strategies via direct nucleophilic ¹⁸F-radiloabeling starting from multi-Curie amounts of [¹⁸F]fluoride, have been recently introduced. In particular, Cu-mediated radiofluorination of arylpinacol boronates and arylstannanes show significant promise for introduction into clinical practice. In this short review these current developments will be discussed with a focus on their applicability to automation. Full article

(This article belongs to the Special Issue Recent Contributions of Female Scientists to the Advancement of Medicinal Chemistry)

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