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Women in Bioorganic Chemistry

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

Deadline for manuscript submissions: closed (20 February 2022) | Viewed by 52461

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editors

Dr. Francesca Cardona

E-Mail Website
Guest Editor
Dipartimento di Chimica "Ugo Schiff", Università degli Studi di Firenze, Via della Lastruccia 3-13, 50019 Sesto Fiorentino, FI, Italy
Interests: synthetic organic chemistry; carbohydrate-based glycomimetics; glycosidase inhibitors; iminosugar synthesis; lysosomal storage diseases; Gaucher disease; Parkinson disease
Special Issues, Collections and Topics in MDPI journals
Dr. Camilla Parmeggiani

E-Mail Website1 Website2
Guest Editor
Dipartimento di Chimica "Ugo Schiff", Università degli Studi di Firenze, Via della Lastruccia 3-13, and European Laboratory for Non Linear Spectroscopy (LENS) via Nello Carrara 1, 50019 Sesto Fiorentino (Firenze), Italy
Interests: liquid crystalline elastomers; smart materials; biomaterials; artificial muscles; functional cell scaffolds; new synthetic approaches; photoresponsive molecules; photoresponsive materials
Dr. Camilla Matassini

E-Mail Website
Guest Editor
Department of Chemistry “Ugo Schiff”, University of Firenze, Via della Lastruccia 3-13, 50019 Sesto Fiorentino (FI), Italy
Interests: nitrogen-containing glycomimetics; new oxidation methods, hypervalent iodine reagents; multivalency; gold glyconanoparticles; glycosidase inhibitors; lysosomal enzymes; pharmacological chaperones; Gaucher–Parkinson relationship
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Recent studies have highlighted that there are still subtle gender biases that put women at a disadvantage when disseminating their research, preventing the science community from benefiting from a wider diversity of voices. In order to embrace gender equality, recognize the career progression of women, and to celebrate the achievements of women in the field of bioorganic chemistry, our journal Molecules will launch a Special Issue on “Women in Bioorganic Chemistry” to be published in 2021.

This Special Issue will include high-quality papers (research articles and short communications) and comprehensive review articles in all areas of bioorganic chemistry. The scope of Special Issue is to cover all range of topics at the organic chemistry-biology interface, including: synthesis of bioactive compounds, biotransformation and enzyme inhibition; enzyme catalysis; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and biosynthesis; antitumoral, antiviral and antimicrobial agents; carbohydrates, lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry; biotechnology, organic materials for biomedical applications and biomaterials.

Contributions in which women are the corresponding authors of the manuscripts are strongly encouraged.

We look forward to receiving your contributions.

Prof. Dr. Francesca Cardona
Dr. Camilla Parmeggiani
Dr. Camilla Matassini
Guest Editors

Manuscript Submission Information

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.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Bioorganic chemistry
  • Synthesis of bioactive compounds
  • Natural compounds
  • Enzyme inhibition
  • Medicinal Chemistry
  • Biomaterials

Published Papers (16 papers)

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Editorial

Jump to: Research, Review

8 pages, 5637 KiB  
Editorial
Women in Bioorganic Chemistry
by Francesca Cardona, Camilla Parmeggiani and Camilla Matassini
Molecules 2022, 27(13), 4290; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27134290 - 04 Jul 2022
Viewed by 1550
Abstract
We are very happy to present this Special Issue, for which we acted as guest editors, and which includes scientific contributions from laboratories headed by women active in the field of bioorganic chemistry [...] Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)

Research

Jump to: Editorial, Review

28 pages, 6982 KiB  
Article
Borylated 2,3,4,5-Tetrachlorophthalimide and Their 2,3,4,5-Tetrachlorobenzamide Analogues: Synthesis, Their Glycosidase Inhibition and Anticancer Properties in View to Boron Neutron Capture Therapy
by David M. Campkin, Yuna Shimadate, Barbara Bartholomew, Paul V. Bernhardt, Robert J. Nash, Jennette A. Sakoff, Atsushi Kato and Michela I. Simone
Molecules 2022, 27(11), 3447; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27113447 - 26 May 2022
Cited by 5 | Viewed by 2084
Abstract
Tetrachlorinated phthalimide analogues bearing a boron-pinacolate ester group were synthesised via two synthetic routes and evaluated in their glycosidase modulating and anticancer properties, with a view to use them in boron neutron capture therapy (BNCT), a promising radiation type for cancer, as this [...] Read more.
Tetrachlorinated phthalimide analogues bearing a boron-pinacolate ester group were synthesised via two synthetic routes and evaluated in their glycosidase modulating and anticancer properties, with a view to use them in boron neutron capture therapy (BNCT), a promising radiation type for cancer, as this therapy does little damage to biological tissue. An unexpected decarbonylation/decarboxylation to five 2,3,4,5-tetrachlorobenzamides was observed and confirmed by X-ray crystallography studies, thus, giving access to a family of borylated 2,3,4,5-tetrachlorobenzamides. Biological evaluation showed the benzamide drugs to possess good to weak potencies (74.7–870 μM) in the inhibition of glycosidases, and to have good to moderate selectivity in the inhibition of a panel of 18 glycosidases. Furthermore, in the inhibition of selected glycosidases, there is a core subset of three animal glycosidases, which is always inhibited (rat intestinal maltase α-glucosidase, bovine liver β-glucosidase and β-galactosidase). This could indicate the involvement of the boron atom in the binding. These glycosidases are targeted for the management of diabetes, viral infections (via a broad-spectrum approach) and lysosomal storage disorders. Assays against cancer cell lines revealed potency in growth inhibition for three molecules, and selectivity for one of these molecules, with the growth of the normal cell line MCF10A not being affected by this compound. One of these molecules showed both potency and selectivity; thus, it is a candidate for further study in this area. This paper provides numerous novel aspects, including expedited access to borylated 2,3,4,5-tetrachlorophthalimides and to 2,3,4,5-tetrachlorobenzamides. The latter constitutes a novel family of glycosidase modulating drugs. Furthermore, a greener synthetic access to such structures is described. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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12 pages, 1650 KiB  
Article
New Chemotypes for the Inhibition of (p)ppGpp Synthesis in the Quest for New Antimicrobial Compounds
by Crescenzo Coppa, Luca Sorrentino, Monica Civera, Marco Minneci, Francesca Vasile and Sara Sattin
Molecules 2022, 27(10), 3097; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27103097 - 12 May 2022
Cited by 3 | Viewed by 2172
Abstract
Antimicrobial resistance (AMR) poses a serious threat to our society from both the medical and economic point of view, while the antibiotic discovery pipeline has been dwindling over the last decades. Targeting non-essential bacterial pathways, such as those leading to antibiotic persistence, a [...] Read more.
Antimicrobial resistance (AMR) poses a serious threat to our society from both the medical and economic point of view, while the antibiotic discovery pipeline has been dwindling over the last decades. Targeting non-essential bacterial pathways, such as those leading to antibiotic persistence, a bacterial bet-hedging strategy, will lead to new molecular entities displaying low selective pressure, thereby reducing the insurgence of AMR. Here, we describe a way to target (p)ppGpp (guanosine tetra- or penta-phosphate) signaling, a non-essential pathway involved in the formation of persisters, with a structure-based approach. A superfamily of enzymes called RSH (RelA/SpoT Homolog) regulates the intracellular levels of this alarmone. We virtually screened several fragment libraries against the (p)ppGpp synthetase domain of our RSH chosen model RelSeq, selected three main chemotypes, and measured their interaction with RelSeq by thermal shift assay and STD-NMR. Most of the tested fragments are selective for the synthetase domain, allowing us to select the aminobenzoic acid scaffold as a hit for lead development. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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12 pages, 1906 KiB  
Article
Binding Interaction of Betulinic Acid to α-Glucosidase and Its Alleviation on Postprandial Hyperglycemia
by Shaodan Chen, Bing Lin, Jiangyong Gu, Tianqiao Yong, Xiong Gao, Yizhen Xie, Chun Xiao, Janis Yaxian Zhan and Qingping Wu
Molecules 2022, 27(8), 2517; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27082517 - 13 Apr 2022
Cited by 9 | Viewed by 2270
Abstract
Inhibiting the intestinal α-glucosidase can effectively control postprandial hyperglycemia for type 2 diabetes mellitus (T2DM) treatment. In the present study, we reported the binding interaction of betulinic acid (BA), a pentacyclic triterpene widely distributed in nature, on α-glucosidase and its alleviation on postprandial [...] Read more.
Inhibiting the intestinal α-glucosidase can effectively control postprandial hyperglycemia for type 2 diabetes mellitus (T2DM) treatment. In the present study, we reported the binding interaction of betulinic acid (BA), a pentacyclic triterpene widely distributed in nature, on α-glucosidase and its alleviation on postprandial hyperglycemia. BA was verified to exhibit a strong inhibitory effect against α-glucosidase with an IC50 value of 16.83 ± 1.16 μM. More importantly, it showed a synergistically inhibitory effect with acarbose. The underlying inhibitory mechanism was investigated by kinetics analysis, surface plasmon resonance (SPR) detection, molecular docking, molecular dynamics (MD) simulation and binding free energy calculation. BA showed a non-competitive inhibition on α-glucosidase. SPR revealed that it had a strong and fast affinity to α-glucosidase with an equilibrium dissociation constant (KD) value of 5.529 × 10−5 M and a slow dissociation. Molecular docking and MD simulation revealed that BA bound to the active site of α-glucosidase mainly due to the van der Waals force and hydrogen bond, and then changed the micro-environment and secondary structure of α-glucosidase. Free energy decomposition indicated amino acid residues such as PHE155, PHE175, HIE277, PHE298, GLU302, TRY311 and ASP347 of α-glucosidase at the binding pocket had strong interactions with BA, while LYS153, ARG210, ARG310, ARG354 and ARG437 showed a negative contribution to binding affinity between BA and α-glucosidase. Significantly, oral administration of BA alleviated the postprandial blood glucose fluctuations in mice. This work may provide new insights into the utilization of BA as a functional food and natural medicine for the control of postprandial hyperglycemia. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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16 pages, 4464 KiB  
Article
Resolution of a Configurationally Stable Hetero[4]helicene
by Michela Lupi, Martina Onori, Stefano Menichetti, Sergio Abbate, Giovanna Longhi and Caterina Viglianisi
Molecules 2022, 27(4), 1160; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27041160 - 09 Feb 2022
Cited by 4 | Viewed by 2489
Abstract
We have developed an efficient chemical resolution of racemic hydroxy substituted dithia-aza[4]helicenes (DTA[4]H) 1(OH) using enantiopure acids as resolving agents. The better diastereomeric separation was achieved on esters prepared with (1S)-(−)-camphanic acid. Subsequent simple manipulations produced highly optically pure (≥ 99% [...] Read more.
We have developed an efficient chemical resolution of racemic hydroxy substituted dithia-aza[4]helicenes (DTA[4]H) 1(OH) using enantiopure acids as resolving agents. The better diastereomeric separation was achieved on esters prepared with (1S)-(−)-camphanic acid. Subsequent simple manipulations produced highly optically pure (≥ 99% enantiomeric excess) (P) and (M)-1(OH) in good yields. The role of the position where the chiral auxiliary is inserted (cape- vs. bay-zone) and the structure of the enantiopure acid used on successful resolution are discussed. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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13 pages, 1088 KiB  
Article
Terpenoid Hydrazones as Biomembrane Penetration Enhancers: FT-IR Spectroscopy and Fluorescence Probe Studies
by Mariia Nesterkina, Serhii Smola, Nataliya Rusakova and Iryna Kravchenko
Molecules 2022, 27(1), 206; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27010206 - 29 Dec 2021
Cited by 6 | Viewed by 2013
Abstract
Hydrazones based on mono- and bicyclic terpenoids (verbenone, menthone and carvone) have been investigated in vitro as potential biomembrane penetration enhancers. In this regard, liposomes composed of lecithin or cardiolipin as phospholipid phase components with incorporated fluorescence probes have been prepared using the [...] Read more.
Hydrazones based on mono- and bicyclic terpenoids (verbenone, menthone and carvone) have been investigated in vitro as potential biomembrane penetration enhancers. In this regard, liposomes composed of lecithin or cardiolipin as phospholipid phase components with incorporated fluorescence probes have been prepared using the thin-film ultrasonic dispersion method. The mean particle size of the obtained liposomes, established using laser diffraction, was found to be 583 ± 0.95 nm, allowing us to categorize them as multilamellar vesicles (MLVs) according to their morphology. Pursuant to fluorescence analysis, we may assume a reduction in microviscosity and, consequently, a decrease in the packing density of lecithin and cardiolipin lipids to be the major mechanism of action for terpenoid hydrazones 1–15. In order to determine the molecular organization of the lipid matrix, lipids were isolated from rat strata cornea (SCs) and their interaction with tested compounds was studied by means of Fourier transform infrared spectroscopy. FT-IR examination suggested that these hydrazones fluidized the SC lipids via the disruption of the hydrogen-bonded network formed by polar groups of SC constituents. The relationship between the structure of terpenoid hydrazones and their ability to enhance biomembrane penetration is discussed. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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24 pages, 1988 KiB  
Article
Synthesis and Biological Evaluation of S-, O- and Se-Containing Dispirooxindoles
by Maksim Kukushkin, Vladimir Novotortsev, Vadim Filatov, Yan Ivanenkov, Dmitry Skvortsov, Mark Veselov, Radik Shafikov, Anna Moiseeva, Nikolay Zyk, Alexander Majouga and Elena Beloglazkina
Molecules 2021, 26(24), 7645; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26247645 - 16 Dec 2021
Cited by 7 | Viewed by 2382
Abstract
A series of novel S-, O- and Se-containing dispirooxindole derivatives has been synthesized using 1,3-dipolar cycloaddition reaction of azomethine ylide generated from isatines and sarcosine at the double C=C bond of 5-indolidene-2-chalcogen-imidazolones (chalcogen was oxygen, sulfur or selenium). The cytotoxicity of these dispiro [...] Read more.
A series of novel S-, O- and Se-containing dispirooxindole derivatives has been synthesized using 1,3-dipolar cycloaddition reaction of azomethine ylide generated from isatines and sarcosine at the double C=C bond of 5-indolidene-2-chalcogen-imidazolones (chalcogen was oxygen, sulfur or selenium). The cytotoxicity of these dispiro derivatives was evaluated in vitro using different tumor cell lines. Several molecules have demonstrated a considerable cytotoxicity against the panel and showed good selectivity towards colorectal carcinoma HCT116 p53+/+ over HCT116 p53−/− cells. In particular, good results have been obtained for LNCaP prostate cell line. The performed in silico study has revealed MDM2/p53 interaction as one of the possible targets for the synthesized molecules. However, in contrast to selectivity revealed during the cell-based evaluation and the results obtained in computational study, no significant p53 activation using a reporter construction in p53wt A549 cell line was observed in a relevant concentration range. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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9 pages, 2430 KiB  
Article
A Galactosidase-Activatable Fluorescent Probe for Detection of Bacteria Based on BODIPY
by Xi Chen, Yu-Cong Liu, Jing-Jing Cui, Fang-Ying Wu and Qiang Xiao
Molecules 2021, 26(19), 6072; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26196072 - 08 Oct 2021
Cited by 7 | Viewed by 2204
Abstract
Pathogenic E. coli infection is one of the most widespread foodborne diseases, so the development of sensitive, reliable and easy operating detection tests is a key issue for food safety. Identifying bacteria with a fluorescent medium is more sensitive and faster than using [...] Read more.
Pathogenic E. coli infection is one of the most widespread foodborne diseases, so the development of sensitive, reliable and easy operating detection tests is a key issue for food safety. Identifying bacteria with a fluorescent medium is more sensitive and faster than using chromogenic media. This study designed and synthesized a β-galactosidase-activatable fluorescent probe BOD-Gal for the sensitive detection of E. coli. It employed a biocompatible and photostable 4,4-difluoro-3a,4a-diaza-s-indancene (BODIPY) as the fluorophore to form a β-O-glycosidic bond with galactose, allowing the BOD-Gal to show significant on-off fluorescent signals for in vitro and in vivo bacterial detection. This work shows the potential for the use of a BODIPY based enzyme substrate for pathogen detection. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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21 pages, 25807 KiB  
Article
New 4-Aminoproline-Based Small Molecule Cyclopeptidomimetics as Potential Modulators of α4β1 Integrin
by Andrea Sartori, Kelly Bugatti, Elisabetta Portioli, Monica Baiula, Irene Casamassima, Agostino Bruno, Francesca Bianchini, Claudio Curti, Franca Zanardi and Lucia Battistini
Molecules 2021, 26(19), 6066; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26196066 - 07 Oct 2021
Cited by 3 | Viewed by 2318
Abstract
Integrin α4β1 belongs to the leukocyte integrin family and represents a therapeutic target of relevant interest given its primary role in mediating inflammation, autoimmune pathologies and cancer-related diseases. The focus of the present work is the design, synthesis and characterization [...] Read more.
Integrin α4β1 belongs to the leukocyte integrin family and represents a therapeutic target of relevant interest given its primary role in mediating inflammation, autoimmune pathologies and cancer-related diseases. The focus of the present work is the design, synthesis and characterization of new peptidomimetic compounds that are potentially able to recognize α4β1 integrin and interfere with its function. To this aim, a collection of seven new cyclic peptidomimetics possessing both a 4-aminoproline (Amp) core scaffold grafted onto key α4β1-recognizing sequences and the (2-methylphenyl)ureido-phenylacetyl (MPUPA) appendage, was designed, with the support of molecular modeling studies. The new compounds were synthesized through SPPS procedures followed by in-solution cyclization maneuvers. The biological evaluation of the new cyclic ligands in cell adhesion assays on Jurkat cells revealed promising submicromolar agonist activity in one compound, namely, the c[Amp(MPUPA)Val-Asp-Leu] cyclopeptide. Further investigations will be necessary to complete the characterization of this class of compounds. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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13 pages, 2749 KiB  
Article
Hybrid Multivalent Jack Bean α-Mannosidase Inhibitors: The First Example of Gold Nanoparticles Decorated with Deoxynojirimycin Inhitopes
by Costanza Vanni, Anne Bodlenner, Marco Marradi, Jérémy P. Schneider, Maria de los Angeles Ramirez, Sergio Moya, Andrea Goti, Francesca Cardona, Philippe Compain and Camilla Matassini
Molecules 2021, 26(19), 5864; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26195864 - 27 Sep 2021
Cited by 7 | Viewed by 3008
Abstract
Among carbohydrate-processing enzymes, Jack bean α-mannosidase (JBα-man) is the glycosidase with the best responsiveness to the multivalent presentation of iminosugar inhitopes. We report, in this work, the preparation of water dispersible gold nanoparticles simultaneously coated with the iminosugar deoxynojirimycin (DNJ) inhitope and simple [...] Read more.
Among carbohydrate-processing enzymes, Jack bean α-mannosidase (JBα-man) is the glycosidase with the best responsiveness to the multivalent presentation of iminosugar inhitopes. We report, in this work, the preparation of water dispersible gold nanoparticles simultaneously coated with the iminosugar deoxynojirimycin (DNJ) inhitope and simple monosaccharides (β-d-gluco- or α-d-mannosides). The display of DNJ at the gold surface has been modulated (i) by using an amphiphilic linker longer than the aliphatic chain used for the monosaccharides and (ii) by presenting the inhitope, not only in monomeric form, but also in a trimeric fashion through combination of a dendron approach with glyconanotechnology. The latter strategy resulted in a strong enhancement of the inhibitory activity towards JBα-man, with a Ki in the nanomolar range (Ki = 84 nM), i.e., more than three orders of magnitude higher than the monovalent reference compound. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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15 pages, 1339 KiB  
Article
α,α-Difluorophosphonohydroxamic Acid Derivatives among the Best Antibacterial Fosmidomycin Analogues
by Aurore Dreneau, Fanny S. Krebs, Mathilde Munier, Chheng Ngov, Denis Tritsch, Didier Lièvremont, Michel Rohmer and Catherine Grosdemange-Billiard
Molecules 2021, 26(16), 5111; https://doi.org/10.3390/molecules26165111 - 23 Aug 2021
Cited by 4 | Viewed by 2214
Abstract
Three α,α-difluorophosphonate derivatives of fosmidomycin were synthesized from diethyl 1,1-difluorobut-3-enylphosphonate and were evaluated on Escherichia coli. Two of them are among the best 1-deoxy-d-xylulose 5-phosphate reductoisomerase inhibitors, with IC50 in the nM range, much better than fosmidomycin, the reference [...] Read more.
Three α,α-difluorophosphonate derivatives of fosmidomycin were synthesized from diethyl 1,1-difluorobut-3-enylphosphonate and were evaluated on Escherichia coli. Two of them are among the best 1-deoxy-d-xylulose 5-phosphate reductoisomerase inhibitors, with IC50 in the nM range, much better than fosmidomycin, the reference compound. They also showed an enhanced antimicrobial activity against E. coli on Petri dishes in comparison with the corresponding phosphates and the non-fluorinated phosphonate. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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18 pages, 3095 KiB  
Article
Novel d-Annulated Pentacyclic Steroids: Regioselective Synthesis and Biological Evaluation in Breast Cancer Cells
by Svetlana K. Vorontsova, Anton V. Yadykov, Alexander M. Scherbakov, Mikhail E. Minyaev, Igor V. Zavarzin, Ekaterina I. Mikhaevich, Yulia A. Volkova and Valerii Z. Shirinian
Molecules 2020, 25(15), 3499; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25153499 - 31 Jul 2020
Cited by 8 | Viewed by 3144
Abstract
The acid-catalyzed cyclization of benzylidenes based on 16-dehydropregnenolone acetate (16-DPA) was studied. It was found that these compounds readily undergo regioselective interrupted Nazarov cyclization with trapping chloride ion and an efficient method of the synthesis of d-annulated pentacyclic steroids based on this [...] Read more.
The acid-catalyzed cyclization of benzylidenes based on 16-dehydropregnenolone acetate (16-DPA) was studied. It was found that these compounds readily undergo regioselective interrupted Nazarov cyclization with trapping chloride ion and an efficient method of the synthesis of d-annulated pentacyclic steroids based on this reaction was proposed. The structures of the synthesized pentacyclic steroids were determined by NMR and X-ray diffraction. It was found that the reaction affords a single diastereomer, but the latter can crystallize as two conformers depending on the structure. Antiproliferative activity of synthesized compounds was evaluated against two breast cancer cell lines: MCF-7 and MDA-MB-231. All tested compounds showed relatively high antiproliferative activity. The synthetic potential of the protocol developed was illustrated by the gram-scale experiment. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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Review

Jump to: Editorial, Research

18 pages, 1364 KiB  
Review
Strigolactones, from Plants to Human Health: Achievements and Challenges
by Valentina Dell’Oste, Francesca Spyrakis and Cristina Prandi
Molecules 2021, 26(15), 4579; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26154579 - 29 Jul 2021
Cited by 20 | Viewed by 4092
Abstract
Strigolactones (SLs) are a class of sesquiterpenoid plant hormones that play a role in the response of plants to various biotic and abiotic stresses. When released into the rhizosphere, they are perceived by both beneficial symbiotic mycorrhizal fungi and parasitic plants. Due to [...] Read more.
Strigolactones (SLs) are a class of sesquiterpenoid plant hormones that play a role in the response of plants to various biotic and abiotic stresses. When released into the rhizosphere, they are perceived by both beneficial symbiotic mycorrhizal fungi and parasitic plants. Due to their multiple roles, SLs are potentially interesting agricultural targets. Indeed, the use of SLs as agrochemicals can favor sustainable agriculture via multiple mechanisms, including shaping root architecture, promoting ideal branching, stimulating nutrient assimilation, controlling parasitic weeds, mitigating drought and enhancing mycorrhization. Moreover, over the last few years, a number of studies have shed light onto the effects exerted by SLs on human cells and on their possible applications in medicine. For example, SLs have been demonstrated to play a key role in the control of pathways related to apoptosis and inflammation. The elucidation of the molecular mechanisms behind their action has inspired further investigations into their effects on human cells and their possible uses as anti-cancer and antimicrobial agents. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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29 pages, 911 KiB  
Review
Molecular Targets of Cannabidiol in Experimental Models of Neurological Disease
by Serena Silvestro, Giovanni Schepici, Placido Bramanti and Emanuela Mazzon
Molecules 2020, 25(21), 5186; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25215186 - 07 Nov 2020
Cited by 41 | Viewed by 6390
Abstract
Cannabidiol (CBD) is a non-psychoactive phytocannabinoid known for its beneficial effects including antioxidant and anti-inflammatory properties. Moreover, CBD is a compound with antidepressant, anxiolytic, anticonvulsant and antipsychotic effects. Thanks to all these properties, the interest of the scientific community for it has grown. [...] Read more.
Cannabidiol (CBD) is a non-psychoactive phytocannabinoid known for its beneficial effects including antioxidant and anti-inflammatory properties. Moreover, CBD is a compound with antidepressant, anxiolytic, anticonvulsant and antipsychotic effects. Thanks to all these properties, the interest of the scientific community for it has grown. Indeed, CBD is a great candidate for the management of neurological diseases. The purpose of our review is to summarize the in vitro and in vivo studies published in the last 15 years that describe the biochemical and molecular mechanisms underlying the effects of CBD and its therapeutic application in neurological diseases. CBD exerts its neuroprotective effects through three G protein coupled-receptors (adenosine receptor subtype 2A, serotonin receptor subtype 1A and G protein-coupled receptor 55), one ligand-gated ion channel (transient receptor potential vanilloid channel-1) and one nuclear factor (peroxisome proliferator-activated receptor γ). Moreover, the therapeutical properties of CBD are also due to GABAergic modulation. In conclusion, CBD, through multi-target mechanisms, represents a valid therapeutic tool for the management of epilepsy, Alzheimer’s disease, multiple sclerosis and Parkinson’s disease. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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18 pages, 1760 KiB  
Review
Identification of Key Functional Motifs of Native Amelogenin Protein for Dental Enamel Remineralisation
by Shama S. M. Dissanayake, Manikandan Ekambaram, Kai Chun Li, Paul W. R. Harris and Margaret A. Brimble
Molecules 2020, 25(18), 4214; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25184214 - 14 Sep 2020
Cited by 15 | Viewed by 7014
Abstract
Dental caries or tooth decay is a preventable and multifactorial disease that affects billions of people globally and is a particular concern in younger populations. This decay arises from acid demineralisation of tooth enamel resulting in mineral loss from the subsurface. The remineralisation [...] Read more.
Dental caries or tooth decay is a preventable and multifactorial disease that affects billions of people globally and is a particular concern in younger populations. This decay arises from acid demineralisation of tooth enamel resulting in mineral loss from the subsurface. The remineralisation of early enamel carious lesions could prevent the cavitation of teeth. The enamel protein amelogenin constitutes 90% of the total enamel matrix protein in teeth and plays a key role in the biomineralisation of tooth enamel. The physiological importance of amelogenin has led to the investigation of the possible development of amelogenin-derived biomimetics against dental caries. We herein review the literature on amelogenin, its primary and secondary structure, comparison to related species, and its’ in vivo processing to bioactive peptide fragments. The key structural motifs of amelogenin that enable enamel remineralisation are discussed. The presence of several motifs in the amelogenin structure (such as polyproline, N- and C-terminal domains and C-terminal orientation) were shown to play a critical role in the formation of particle shape during remineralization. Understanding the function/structure relationships of amelogenin can aid in the rational design of synthetic polypeptides for biomineralisation, halting enamel loss and leading to improved therapies for tooth decay. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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17 pages, 1164 KiB  
Review
New Frontiers on Human Safe Insecticides and Fungicides: An Opinion on Trehalase Inhibitors
by Camilla Matassini, Camilla Parmeggiani and Francesca Cardona
Molecules 2020, 25(13), 3013; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25133013 - 01 Jul 2020
Cited by 23 | Viewed by 4167
Abstract
In the era of green economy, trehalase inhibitors represent a valuable chance to develop non-toxic pesticides, being hydrophilic compounds that do not persist in the environment. The lesson on this topic that we learned from the past can be of great help in [...] Read more.
In the era of green economy, trehalase inhibitors represent a valuable chance to develop non-toxic pesticides, being hydrophilic compounds that do not persist in the environment. The lesson on this topic that we learned from the past can be of great help in the research on new specific green pesticides. This review aims to describe the efforts made in the last 50 years in the evaluation of natural compounds and their analogues as trehalase inhibitors, in view of their potential use as insecticides and fungicides. Specifically, we analyzed trehalase inhibitors based on sugars and sugar mimics, focusing on those showing good inhibition properties towards insect trehalases. Despite their attractiveness as a target, up to now there are no trehalase inhibitors that have been developed as commercial insecticides. Although natural complex pseudo di- and trisaccharides were firstly studied to this aim, iminosugars look to be more promising, showing an excellent specificity profile towards insect trehalases. The results reported here represent an overview and a discussion of the best candidates which may lead to the development of an effective insecticide in the future. Full article
(This article belongs to the Special Issue Women in Bioorganic Chemistry)
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