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A special issue of Pharmaceuticals (ISSN 1424-8247). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (31 December 2021) | Viewed by 46577

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Dr. Jean Jacques Vanden Eynde

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Formerly Head, Department of Organic Chemistry (FS), University of Mons-UMONS, 7000 Mons, Belgium
Interests: heterocycles; medicinal chemistry; green chemistry; microwave-induced synthesis
Special Issues, Collections and Topics in MDPI journals

Dr. Annie Mayence

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Formerly Professor, Haute Ecole Provinciale de Hainaut-Condorcet, 7330 Saint-Ghislain, Belgium
Interests: medicinal chemistry; organic synthesis; parasitic diseases; orphan drugs
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Past decades have seen the birth of innovative technologies and strategies enabling the medicinal chemist to explore new therapeutic opportunities and better contribute to improvements in health and wellbeing.

Exceptional progress has been made in microwave- and ultrasound-assisted syntheses, mechanochemistry, multi-component reactions, combinatorial chemistry, high-throughput screenings, computational studies, analytical methods, spectroscopy and imaging, and many other topics of critical importance in modern pharmaceutical sciences.

This Topical Collection is aimed at giving our readers a vast overview of these innovations and how they can be exploited to advance scientific knowledge and understanding in drug discovery and development.

Dr. Jean Jacques Vanden Eynde
Dr. Annie Mayence
Collection Editors

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Keywords

catalysis
in silico
in vitro
flow
one-pot
microreactors
microwave
mix and divide
screening
solid-phase synthesis
solvent-free reactions
ultrasound
virtual screening
supercritical conditions

Published Papers (12 papers)

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Research

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14 pages, 1908 KiB

Open AccessArticle

Synthesis and Biological Characterization of the New Glycolipid Lactose Undecylenate (URB1418)

by Michele Verboni, Serena Benedetti, Raffaella Campana, Francesco Palma, Lucia Potenza, Maurizio Sisti, Andrea Duranti and Simone Lucarini

Pharmaceuticals 2022, 15(4), 456; https://0-doi-org.brum.beds.ac.uk/10.3390/ph15040456 - 08 Apr 2022

Cited by 4 | Viewed by 1871

Abstract

As a follow-up to our previous studies on glycolipid surfactants, a new molecule, that is lactose 6′-O-undecylenate (URB1418), was investigated. To this end, a practical synthesis and studies aimed at exploring its specific properties were carried out. URB1418 showed antifungal activities against Trichophyton rubrum F2 and Candida albicans ATCC 10231 (MIC 512 μg/mL) and no significant antibacterial activity against Staphylococcus aureus and Pseudomonas aeruginosa. At the same time, it presented anti-inflammatory properties, as documented by the dose-dependent reduction in LPS-induced NO release in RAW 264.7 cells, while a low antioxidant capacity in the range of concentrations tested (EC₅₀ > 200 µM) was also observed. Moreover, URB1418 offers the advantage of being more stable than the reference polyunsaturated lactose esters and of being synthesized using a “green” procedure, involving an enzymatic method, high yield and low manufacturing cost. For all these reasons and the absence of toxicity (HaCaT cells), the new glycolipid presented herein could be considered an interesting compound for applications in various fields. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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10 pages, 1635 KiB

Open AccessFeature PaperArticle

Synthesis of Silver Nanoparticles Using Odontosoria chinensis (L.) J. Sm. and Evaluation of their Biological Potentials

by Marimuthu alias Antonysamy Johnson, Thangaiah Shibila, Santhanam Amutha, Irwin R. A. Menezes, José G. M. da Costa, Nadghia F. L. Sampaio and Henrique D. M. Coutinho

Pharmaceuticals 2020, 13(4), 66; https://0-doi-org.brum.beds.ac.uk/10.3390/ph13040066 - 13 Apr 2020

Cited by 13 | Viewed by 2774

Abstract

The present study was aimed to synthesize silver nanoparticles (AgNPs) from the aqueous extracts of Odontosoria chinensis (L.) J. Sm. and the synthesized AgNPs were examined for their biopotentials. The Odontosoria chinensis extracts were added to 1 mM AgNO₃ solution with different ratios viz., 0.5:9.5, 1:9, 1.5:8.5 and 2:8 ratios for the reduction of Ag ions. After reduction, the AgNPs of Odontosoria chinensis were analyzed spectroscopically for further confirmation. The synthesized AgNPs of Odontosoria chinensis were characterized by pH, ultra violet–visible spectroscopy (UV-Vis), Fourier transform–infra red spectroscopy (FT-IR), scanning electron microscopy-energy dispersive X-ray analysis (SEM-EDAX) and X-Ray diffraction (XRD). The time taken for the complete reduction of Silver (Ag) in solution to nanoparticle was 10 min. The O. chinensis aqueous extracts mediated silver nanoparticles showed a broad peak with distinct absorption at around 400–420 nm and confirmed the silver nanoparticle formation. FT-IR results also confirmed the existence of organic materials in the silver nanoparticles of O. chinensis. The EDX spectra of AgNPs of O. chinenesis revealed the occurrence of a strong Ag peak. The synthesis of AgNPs of O. chinenesis was confirmed with the existence of a peak at 46.228°. The toxic potential of AgNPs of O. chinenesis showed varied percentage mortality with the LC₅₀ values of 134.68 μL/ 50 mL and 76.5 μL/50 mL, respectively. The anti-inflammatory and anti-diabetic activities of aqueous and AgNPs of O. chinenesis were statistically significant at p < 0.05 level. Conclusion: The results demonstrated the toxicity, anti-diabetic and anti-inflammatory potential of the studied AgNPs. The synthesized nanoparticles of Odontosoria chinensis could be tested as an alternative to anticancer, anti-diabetic and anti-inflammatory drugs. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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14 pages, 2228 KiB

Open AccessArticle

Production and Characterization of Chitosan–Polyanion Nanoparticles by Polyelectrolyte Complexation Assisted by High-Intensity Sonication for the Modified Release of Methotrexate

by Yhors Ciro, John Rojas, Maria J. Alhajj, Gustavo A. Carabali and Constain H. Salamanca

Pharmaceuticals 2020, 13(1), 11; https://0-doi-org.brum.beds.ac.uk/10.3390/ph13010011 - 08 Jan 2020

Cited by 24 | Viewed by 3327

Abstract

A promising strategy to improve the effectivity of anticancer treatment and decrease its side effects is to modulate drug release by using nanoparticulates (NPs) as carriers. In this study, methotrexate-loaded chitosan–polyanion nanoparticles were produced by polyelectrolyte complexation assisted by high-intensity sonication, using several anionic polymers, such as the sodium and potassium salts of poly(maleic acid-alt-ethylene) and poly(maleic acid-alt-octadecene), here named PAM-2 and PAM-18, respectively. Such NPs were analyzed and characterized according to particle size, polydispersity index, zeta potential and encapsulation efficiency. Likewise, their physical stability was tested at 4 °C and 40 °C in order to evaluate any change in the previously mentioned particle parameters. The in vitro methotrexate release was assessed at a pH of 7.4, which simulated physiological conditions, and the data were fitted to the heuristic models of order one, Higuchi, Peppas–Sahlin and Korsmeyer–Peppas. The results revealed that most of the MTX-chitosan–polyanion NPs have positive zeta potential values, sizes <280 nm and monodisperse populations, except for the NPs formed with PAM-18 polyanions. Further, the NPs showed adequate physical stability, preventing NP–NP aggregation. Likewise, these carriers modified the MTX release by an anomalous mechanism, where the NPs formed with PAM-2 polymer led to a release mechanism controlled by diffusion and relaxation, whereas the NPs formed with PAM-18 led to a mainly diffusion-controlled release mechanism. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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17 pages, 3742 KiB

Open AccessArticle

Bio- Fortification of Angelica gigas Nakai Nano-Powder Using Bio-Polymer by Hot Melt Extrusion to Enhance the Bioaccessibility and Functionality of Nutraceutical Compounds

by Md Obyedul Kalam Azad, Wie Soo Kang, Jung Dae Lim and Cheol Ho Park

Pharmaceuticals 2020, 13(1), 3; https://0-doi-org.brum.beds.ac.uk/10.3390/ph13010003 - 25 Dec 2019

Cited by 8 | Viewed by 3496

Abstract

Angelica gigas Nakai (AGN) is a popular traditional herbal medicine which has been used to alleviate various human diseases in Korea since ancient times. However, the low bioaccessibility of the nutraceutical compounds of AGN results in a poor water solubility, thereby limiting bioavailability. In this regard, a ternary AGN–biopolymer–plasticizer composite (AGNC) was developed to enhance the bioaccessibility of nutraceutical compounds from extrudate AGN formulations manufactured by hot melt extrusion (HME). The AGNC was prepared with extrudate AGN (EAGN) using different hydroxypropyl methylcellulose (HPMC) biopolymers (5% w/w) viz.: hypromellose phthalate (HP), hypromellose (AN), and hypromellose (CN) along with acetic acid (AA) (0.1 M, 20% w/v) as a plasticizer. The non-extrudate fresh AGN (FAGN) powder was used as a control. The physicochemical properties of the extrudate formulations and control were characterized by differential scanning calorimetry (DSC) and Fourier-transform infrared spectroscopy (FTIR). DSC analysis showed a lower enthalpy (ΔH) (12.22 J/g) and lower glass transition temperature (T_g) (41 °C) in HP-AA-EAGN compared to the control. FTIR confirmed the physical crosslinking between AGN and biopolymer in the extrudate composite and demonstrated that some functional groups formed viz., -OH and -CH₂. The obtained result also shows that the particle size was reduced by 341 nm, and solubility was increased by 65.5% in HP-AA-EAGN compared to the control (1499 nm, 29.4%, respectively). The bioaccessibility of the total phenolic content and the total flavonoids—including decursin (D) and decursinol angelate (DA)—were significantly higher in HP-AA-EAGN compared to the control. The 2,2-diphenyl-1 picryl hydrazyl (DPPH) free radical scavenging capacity and ferric reducing antioxidant power assay (FRAP) indicated that the HP-AA-EAGN formulation preserves a greater antioxidant profile than the other formulations. Finally, it is summarized that the addition of acidified HP biopolymer increased the bioaccessibility, functionality, and improved the physicochemical properties of nutraceutical compounds in the extrudate AGN formulation. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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19 pages, 2270 KiB

Open AccessArticle

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

by Raffaella Campana, Alessio Merli, Michele Verboni, Francesca Biondo, Gianfranco Favi, Andrea Duranti and Simone Lucarini

Pharmaceuticals 2019, 12(4), 186; https://0-doi-org.brum.beds.ac.uk/10.3390/ph12040186 - 17 Dec 2019

Cited by 21 | Viewed by 4417

Abstract

A small library of sugar-based (i.e., glucose, mannose and lactose) monoesters containing hydrophobic aliphatic or aromatic tails were synthesized and tested. The antimicrobial activity of the compounds against a target panel of Gram-positive, Gram-negative and fungi was assessed. Based on this preliminary screening, the antibiofilm activity of the most promising molecules was evaluated at different development times of selected food-borne pathogens (E. coli, L. monocytogenes, S. aureus, S. enteritidis). The antibiofilm activity during biofilm formation resulted in the following: mannose C10 > lactose biphenylacetate > glucose C10 > lactose C10. Among them, mannose C10 and lactose biphenylacetate showed an inhibition for E. coli 97% and 92%, respectively. At MICs values, no toxicity was observed on Caco-2 cell line for all the examined compounds. Overall, based on these results, all the sugar-based monoesters showed an interesting profile as safe antimicrobial agents. In particular, mannose C10 and lactose biphenylacetate are the most promising as possible biocompatible and safe preservatives for pharmaceutical and food applications. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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12 pages, 2067 KiB

Open AccessCommunication

In Vitro Characterization and Stability Profiles of Antibody–Fluorophore Conjugates Derived from Interchain Cysteine Cross-Linking or Lysine Bioconjugation

by Camille Martin, Guillaume Brachet, Cyril Colas, Emilie Allard-Vannier, Claire Kizlik-Masson, Clara Esnault, Renaud Respaud, Caroline Denevault-Sabourin, Igor Chourpa, Valérie Gouilleux-Gruart, Marie-Claude Viaud-Massuard and Nicolas Joubert

Pharmaceuticals 2019, 12(4), 176; https://0-doi-org.brum.beds.ac.uk/10.3390/ph12040176 - 02 Dec 2019

Cited by 8 | Viewed by 4229

Abstract

Fluorescent labelling of monoclonal antibodies (mAbs) is classically performed by chemical bioconjugation methods. The most frequent labelling technique to generate antibody–fluorophore conjugates (AFCs) involves the bioconjugation onto the mAb lysines of a dye bearing an N-hydroxysuccinimide ester or an isothiocyanate group. However, discrepancies between labelling experiments or kits can be observed, related to reproducibility issues, alteration of antigen binding, or mAb properties. The lack of information on labelling kits and the incomplete characterization of the obtained labelled mAbs largely contribute to these issues. In this work, we generated eight AFCs through either lysine or interchain cysteine cross-linking bioconjugation of green-emitting fluorophores (fluorescein or BODIPY) onto either trastuzumab or rituximab. This strategy allowed us to study the influence of fluorophore solubility, bioconjugation technology, and antibody nature on two known labelling procedures. The structures of these AFCs were thoroughly analyzed by mass spectroscopy, and their antigen binding properties were studied. We then compared these AFCs in vitro by studying their respective spectral properties and stabilities. The shelf stability profiles and sensibility to pH variation of these AFCs prove to be dye-, antibody- and labelling-technology-dependent. Fluorescence emission in AFCs was higher when lysine labelling was used, but cross-linked AFCs were revealed to be more stable. This must be taken into account for the design of any biological study involving antibody labelling. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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21 pages, 3589 KiB

Open AccessFeature PaperArticle

Study of Iron Piperazine-Based Chelators as Potential Siderophore Mimetics

by Pauline Loupias, Isabelle Dechamps-Olivier, Laurent Dupont, Pierre Vanlemmens, Catherine Mullié, Nicolas Taudon, Anne Bouchut, Alexandra Dassonville-Klimpt and Pascal Sonnet

Pharmaceuticals 2019, 12(4), 160; https://0-doi-org.brum.beds.ac.uk/10.3390/ph12040160 - 23 Oct 2019

Cited by 7 | Viewed by 4277

Abstract

Gram-negative bacteria’s resistance such as Pseudomonas aeruginosa and the Burkholderia group to conventional antibiotics leads to therapeutic failure. Use of siderophores as Trojan horses to internalize antibacterial agents or toxic metals within bacteria is a promising strategy to overcome resistance phenomenon. To combat the Pseudomonas sp, we have synthesized and studied two piperazine-based siderophore mimetics carrying either catecholate moieties (1) or hydroxypyridinone groups (2) as iron chelators. These siderophore-like molecules were prepared in no more than four steps with good global yields. The physicochemical study has highlighted a strong iron affinity since their pFe values were higher than 20. 1 possesses even a pFe value superior than those of pyoverdine, the P. aeruginosa endogenous siderophore, suggesting its potential ability to compete with it. At physiological pH, 1 forms mainly a 2:3 complex with iron, whereas two species are observed for 2. Unfortunately, the corresponding Ga(III)-1 and 2 complexes showed no antibacterial activity against P. aeruginosa DSM 1117 strain. The evaluation of their siderophore-like activity showed that 1 and 2 could be internalized by the bacteria. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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12 pages, 1682 KiB

Open AccessArticle

Cardiolipin-Based Lipopolyplex Platform for the Delivery of Diverse Nucleic Acids into Gram-Negative Bacteria

by Federico Perche, Tony Le Gall, Tristan Montier, Chantal Pichon and Jean-Marc Malinge

Pharmaceuticals 2019, 12(2), 81; https://0-doi-org.brum.beds.ac.uk/10.3390/ph12020081 - 28 May 2019

Cited by 9 | Viewed by 3606

Abstract

Antibiotic resistance is a growing public health concern. Because only a few novel classes of antibiotics have been developed in the last 40 years, such as the class of oxazolidinones, new antibacterial strategies are urgently needed (Coates, A.R. et al., 2011). Nucleic acid-based antibiotics are a new type of antimicrobials. However, free nucleic acids cannot spontaneously cross the bacterial cell wall and membrane; consequently, their intracellular delivery into bacteria needs to be assisted. Here, we introduce an original lipopolyplex system named liposome polymer nucleic acid (LPN), capable of versatile nucleic acid delivery into bacteria. We characterized LPN formed with significant therapeutic nucleic acids: 11 nt antisense single-stranded (ss) DNA and double-stranded (ds) DNA of 15 and 95 base pairs (bp), 9 kbp plasmid DNA (pDNA), and 1000 nt ssRNA. All these complexes were efficiently internalized by two different bacterial species, i.e., Escherichia coli and Pseudomonas aeruginosa, as shown by flow cytometry. Consistent with intracellular delivery, LPN prepared with an antisense oligonucleotide and directed against an essential gene, induced specific and important bacterial growth inhibition likely leading to a bactericidal effect. Our findings indicate that LPN is a versatile platform for efficient delivery of diverse nucleic acids into Gram-negative bacteria. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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12 pages, 945 KiB

Open AccessArticle

Retinal Gene Distribution and Functionality Implicated in Inherited Retinal Degenerations Can Reveal Disease-Relevant Pathways for Pharmacologic Intervention

by Debarshi Mustafi, Amirmohsen Arbabi, Hossein Ameri and Krzysztof Palczewski

Pharmaceuticals 2019, 12(2), 74; https://0-doi-org.brum.beds.ac.uk/10.3390/ph12020074 - 17 May 2019

Cited by 4 | Viewed by 4148

Abstract

The advent of genetic therapies for inherited retinal diseases (IRDs) has spurred the need for precise diagnosis and understanding of pathways for therapeutic targeting. The majority of IRDs that are clinically diagnosed, however, lack an identifiable mutation in established disease-causing loci and thus can be investigated with limited rational drug discovery methods. Transcriptome profiling of the retina can reveal the functional state of the tissue, and geographic profiling can uncover the various clinical phenotypic presentations of IRDs and aid in pharmaceutical intervention. In this investigation, we detail the retinal geographic expression of known retinal disease-causing genes in the primate retina and functional targetable pathways in specific IRDs. Understanding the genetic basis as well as the resulting functional consequences will assist in the discovery of future therapeutic interventions and provide novel insights to medicinal chemists. Herein, we report that, despite the genetic heterogeneity of retinal diseases, potential functional pathways can be elucidated for therapeutic targeting and be used for predictive phenotypic and genotypic modeling of novel IRD presentations. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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Review

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35 pages, 6666 KiB

Open AccessReview

Ultrasound for Drug Synthesis: A Green Approach

by Micheline Draye, Gregory Chatel and Romain Duwald

Pharmaceuticals 2020, 13(2), 23; https://0-doi-org.brum.beds.ac.uk/10.3390/ph13020023 - 31 Jan 2020

Cited by 47 | Viewed by 5860

Abstract

This last century, the development of new medicinal molecules represents a real breakthrough in terms of humans and animal life expectancy and quality of life. However, this success is tainted by negative environmental consequences. Indeed, the synthesis of drug candidates requires the use of many chemicals, solvents, and processes that are very hazardous, toxic, energy consuming, expensive, and generates a large amount of waste. Many large pharmaceutical companies have thus moved to using green chemistry practices for drug discovery, development, and manufacturing. One of them is the use of energy-efficient activation techniques, such as ultrasound. This review summarizes the latest most representative works published on the use of ultrasound for sustainable bioactive molecules synthesis. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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23 pages, 17035 KiB

Open AccessReview

Predictive Power of In Silico Approach to Evaluate Chemicals against M. tuberculosis: A Systematic Review

by Giulia Oliveira Timo, Rodrigo Souza Silva Valle dos Reis, Adriana Françozo de Melo, Thales Viana Labourdette Costa, Pérola de Oliveira Magalhães and Mauricio Homem-de-Mello

Pharmaceuticals 2019, 12(3), 135; https://0-doi-org.brum.beds.ac.uk/10.3390/ph12030135 - 16 Sep 2019

Cited by 9 | Viewed by 4127

Abstract

Mycobacterium tuberculosis (Mtb) is an endemic bacterium worldwide that causes tuberculosis (TB) and involves long-term treatment that is not always effective. In this context, several studies are trying to develop and evaluate new substances active against Mtb. In silico techniques are often used to predict the effects on some known target. We used a systematic approach to find and evaluate manuscripts that applied an in silico technique to find antimycobacterial molecules and tried to prove its predictive potential by testing them in vitro or in vivo. After searching three different databases and applying exclusion criteria, we were able to retrieve 46 documents. We found that they all follow a similar screening procedure, but few studies exploited equal targets, exploring the interaction of multiple ligands to 29 distinct enzymes. The following in vitro/vivo analysis showed that, although the virtual assays were able to decrease the number of molecules tested, saving time and money, virtual screening procedures still need to develop the correlation to more favorable in vitro outcomes. We find that the in silico approach has a good predictive power for in vitro results, but call for more studies to evaluate its clinical predictive possibilities. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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12 pages, 1191 KiB

Open AccessBrief Report

6′-O-Lactose Ester Surfactants as an Innovative Opportunity in the Pharmaceutical Field: From Synthetic Methods to Biological Applications

by Michele Verboni, Simone Lucarini and Andrea Duranti

Pharmaceuticals 2021, 14(12), 1306; https://0-doi-org.brum.beds.ac.uk/10.3390/ph14121306 - 15 Dec 2021

Cited by 13 | Viewed by 2809

Abstract

Glycolipid surfactants are biocompatible and biodegradable compounds characterized by potential applications in various sectors including pharmaceuticals, cosmetics, agriculture, and food production. A specific overview regarding synthetic methodologies and properties of 6′-lactose-based surfactants is presented herein, particularly all the synthetic approaches to this class of lactose esters, such as enzymatic and traditional organic syntheses. Moreover, detailed descriptions of physicochemical data and biocompatibility properties of these molecules, that is, surface tension, critical micelle concentration, emulsifying ability, foaming, particle size distribution, biocompatibility, and safety, are described. Biological applications with a focus on permeability enhancing, antimicrobial activity, and antibiofilm properties of 6′-lactose-based esters are also reported. Full article

(This article belongs to the Special Issue New Tools for Medicinal Chemists)

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