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  1. Article ; Online: The Odd Couple(s)

    Margherita De Rosa / Anna Verdino / Annunziata Soriente / Anna Marabotti

    International Journal of Molecular Sciences, Vol 22, Iss 2, p

    An Overview of Beta-Lactam Antibiotics Bearing More Than One Pharmacophoric Group

    2021  Volume 617

    Abstract: β-lactam antibiotics are among the most important and widely used antimicrobials worldwide and are comprised of a large family of compounds, obtained by chemical modifications of the common scaffolds. Usually these modifications include the addition of ... ...

    Abstract β-lactam antibiotics are among the most important and widely used antimicrobials worldwide and are comprised of a large family of compounds, obtained by chemical modifications of the common scaffolds. Usually these modifications include the addition of active groups, but less frequently, molecules were synthesized in which either two β-lactam rings were joined to create a single bifunctional compound, or the azetidinone ring was joined to another antibiotic scaffold or another molecule with a different activity, in order to create a molecule bearing two different pharmacophoric functions. In this review, we report some examples of these derivatives, highlighting their biological properties and discussing how this strategy can lead to the development of innovative antibiotics that can represent either novel weapons against the rampant increase of antimicrobial resistance, or molecules with a broader spectrum of action.
    Keywords bis-azetidinone derivatives ; dual antibiotics ; podands ; siderophores ; bis beta-lactam ; bis beta-lactam macrocycles ; Biology (General) ; QH301-705.5 ; Chemistry ; QD1-999
    Subject code 540
    Language English
    Publishing date 2021-01-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  2. Article ; Online: Characterization of Linezolid-Analogue L3-Resistance Mutation in Staphylococcus aureus

    Anna Zanfardino / Michela Di Napoli / Federica Migliore / Bruno Hay Mele / Annunziata Soriente / Margherita De Rosa / Eugenio Notomista / Mario Varcamonti

    Microorganisms, Vol 11, Iss 700, p

    2023  Volume 700

    Abstract: In a previous study, a linezolid analogue, called 10f, was synthesized. The 10f molecule has an antimicrobial activity comparable to that of the parental compound. In this study, we isolated a Staphylococcus aureus ( S. aureus ) strain resistant to 10f. ... ...

    Abstract In a previous study, a linezolid analogue, called 10f, was synthesized. The 10f molecule has an antimicrobial activity comparable to that of the parental compound. In this study, we isolated a Staphylococcus aureus ( S. aureus ) strain resistant to 10f. After sequencing the 23S rRNA and the ribosomal proteins L3 (rplC) and L4 (rplD) genes, we found that the resistant phenotype was associated with a single mutation G359U in rplC bearing to the missense mutation G120V in the L3 protein. The identified mutation is far from the peptidyl transferase center, the oxazolidinone antibiotics binding site, thus suggesting that we identified a new and interesting example of a long-range effect in the ribosome structure.
    Keywords linezolid analogue ; antibiotic resistance ; antimicrobial activity ; Biology (General) ; QH301-705.5
    Language English
    Publishing date 2023-03-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  3. Article ; Online: Hexahexyloxycalix[6]arene, a Conformationally Adaptive Host for the Complexation of Linear and Branched Alkylammonium Guests

    Veronica Iuliano / Carmen Talotta / Paolo Della Sala / Margherita De Rosa / Annunziata Soriente / Placido Neri / Carmine Gaeta

    Molecules, Vol 28, Iss 4749, p

    2023  Volume 4749

    Abstract: Hexahexyloxycalix[6]arene 2b leads to the endo -cavity complexation of linear and branched alkylammonium guests showing a conformational adaptive behavior in CDCl 3 solution. Linear n -pentylammonium guest 6a + induces the cone conformation of 2b at the ... ...

    Abstract Hexahexyloxycalix[6]arene 2b leads to the endo -cavity complexation of linear and branched alkylammonium guests showing a conformational adaptive behavior in CDCl 3 solution. Linear n -pentylammonium guest 6a + induces the cone conformation of 2b at the expense of the 1,2,3-alternate, which is the most abundant conformer of 2b in the absence of a guest. In a different way, branched alkylammonium guests, such as tert -butylammonium 6b + and isopropylammonium 6c + , select the 1,2,3-alternate as the favored 2b conformation ( 6b + / 6c + ⊂ 2b 1,2,3-alt ), but other complexes in which 2b adopts different conformations, namely, 6b + / 6c + ⊂ 2b cone , 6b + / 6c + ⊂ 2b paco , and 6b + / 6c + ⊂ 2b 1,2-alt , have also been revealed. Binding constant values determined via NMR experiments indicated that the 1,2,3-alternate was the best-fitting 2b conformation for the complexation of branched alkylammonium guests, followed by cone > paco > 1,2-alt. Our NCI and NBO calculations suggest that the H-bonding interactions ( + N–H···O) between the ammonium group of the guest and the oxygen atoms of calixarene 2b are the main determinants of the stability order of the four complexes. These interactions are weakened by increasing the guest steric encumbrance, thus leading to a lower binding affinity. Two stabilizing H-bonds are possible with the 1,2,3-alt- and cone- 2b conformations, whereas only one H-bond is possible with the other paco- and 1,2-alt- 2b stereoisomers.
    Keywords conformation ; calixarene ; molecular recognition ; alkylammonium guests ; Organic chemistry ; QD241-441
    Subject code 333
    Language English
    Publishing date 2023-06-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  4. Article ; Online: Multiple threading of a triple-calix[6]arene host

    Veronica Iuliano / Roberta Ciao / Emanuele Vignola / Carmen Talotta / Patrizia Iannece / Margherita De Rosa / Annunziata Soriente / Carmine Gaeta / Placido Neri

    Beilstein Journal of Organic Chemistry, Vol 15, Iss 1, Pp 2092-

    2019  Volume 2104

    Abstract: The synthesis of the triple-calix[6]arene derivative 6 in which three calix[6]arene macrocycles are linked to a central 1,3,5-trimethylbenzene moiety is reported. Derivative 6 is able to give multiple-threading processes in the presence of ... ...

    Abstract The synthesis of the triple-calix[6]arene derivative 6 in which three calix[6]arene macrocycles are linked to a central 1,3,5-trimethylbenzene moiety is reported. Derivative 6 is able to give multiple-threading processes in the presence of dialkylammonium axles. The formation of pseudo[2]rotaxane, pseudo[3]rotaxane, and pseudo[4]rotaxane by threading one, two, and three, respectively, calix-wheels of 6 has been studied by 1D and 2D NMR, DOSY, and ESI-FT-ICR MS/MS experiments. The use of a directional alkylbenzylammonium axle led to the stereoselective formation of endo-alkyl pseudo[n]rotaxane stereoisomers.
    Keywords calixarene ; multiple-threading ; pseudo[n]rotaxane ; stereoisomers ; Science ; Q ; Organic chemistry ; QD241-441
    Language English
    Publishing date 2019-09-01T00:00:00Z
    Publisher Beilstein-Institut
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  5. Article: Exploiting the p-Bromodienone Route for the Formation and Trapping of Calixarene Oxenium Cations with Enamine Nucleophiles

    Soriente, Annunziata / Aldo Spinella / Carmen Talotta / Carmine Gaeta / Margherita De Rosa / Pellegrino La Manna / Placido Neri

    Journal of organic chemistry. 2018 May 09, v. 83, no. 11

    2018  

    Abstract: This study shows that calixarene p-bromodienone derivatives can act as precursors for the formation of oxenium cations, which can be trapped with enamine C-nucleophiles. When calixarene p-bromodienones were treated with enamines, in the presence of ... ...

    Abstract This study shows that calixarene p-bromodienone derivatives can act as precursors for the formation of oxenium cations, which can be trapped with enamine C-nucleophiles. When calixarene p-bromodienones were treated with enamines, in the presence of AgClO4, the lower rim-substituted C–O–C products were obtained by an electrophilic attack of the intermediate calixarene-oxenium cation with a contemporary cone-to-partial-cone inversion of the involved aromatic ring.
    Keywords aromatic compounds ; cations ; chemical reactions ; chemical structure ; enamines ; Lewis acids ; Lewis bases ; organic chemistry
    Language English
    Dates of publication 2018-0509
    Size p. 5947-5953.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.8b00431
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  6. Article ; Online: Novel Penicillin-Type Analogues Bearing a Variable Substituted 2-Azetidinone Ring at Position 6

    Margherita De Rosa / Giovanni Vigliotta / Giuseppe Palma / Carmela Saturnino / Annunziata Soriente

    Molecules, Vol 20, Iss 12, Pp 22044-

    Synthesis and Biological Evaluation

    2015  Volume 22057

    Abstract: The synthesis and the biological activity of novel semi-synthetic β-lactam compounds containing an azetidinone moiety joined to the amino-nitrogen of the (+)-6-aminopenicillanic acid (6-APA) as new antibacterial agents is reported. The synthesized ... ...

    Abstract The synthesis and the biological activity of novel semi-synthetic β-lactam compounds containing an azetidinone moiety joined to the amino-nitrogen of the (+)-6-aminopenicillanic acid (6-APA) as new antibacterial agents is reported. The synthesized compounds were screened for their in vitro antimicrobial activity against a panel of Gram positive and Gram negative pathogens and environmental bacteria. Tested compounds displayed good antimicrobial activity against all tested Gram positive bacteria and for Staphylococcus aureus and Staphylococcus epidermidis antimicrobial activity resulted higher than that of the reference antibiotic. Additionally, in vitro cytotoxic screening was also carried out indicating that the compounds do not cause a cell vitality reduction effective at concentration next to and above those shown to be antimicrobial.
    Keywords 6-aminopenicillanic acid (6-APA) ; 2-azetidinone ; β-lactam antibiotics ; antibacterial ; Staudinger reaction ; Organic chemistry ; QD241-441
    Subject code 540
    Language English
    Publishing date 2015-12-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  7. Article: Negative Solvatochromism in a N-Linked p-Pyridiniumcalix[4]arene Derivative

    Iuliano, Veronica / Carmen Talotta / Carmine Gaeta / Annunziata Soriente / Margherita De Rosa / Silvano Geremia / Neal Hickey / Benedetta Mennucci / Placido Neri

    Organic letters. 2019 Apr. 02, v. 21, no. 8

    2019  

    Abstract: In this paper, we report the synthesis, structural characterization, and solvatochromic properties of a N-linked p-pyridiniumcalix[4]arenediol derivative 1. In the solid state, 1 forms a dimeric assembly stabilized by a network of weak H-bonding ... ...

    Abstract In this paper, we report the synthesis, structural characterization, and solvatochromic properties of a N-linked p-pyridiniumcalix[4]arenediol derivative 1. In the solid state, 1 forms a dimeric assembly stabilized by a network of weak H-bonding interactions involving acetonitrile solvent molecules. In solution, 1 shows a peculiar negative solvatochromism which was rationalized with the aid of TD-DFT calculations. The species responsible for this phenomenon is the monodeprotonated betainic form of 1 which is easily formed at pH close to neutrality.
    Keywords acetonitrile ; aromatic hydrocarbons ; chemical reactions ; chemical structure ; hydrogen bonding ; pH ; solvents
    Language English
    Dates of publication 2019-0402
    Size p. 2704-2707.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.9b00683
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  8. Article ; Online: Synthesis and biological evaluation of the progenitor of a new class of cephalosporin analogues, with a particular focus on structure-based computational analysis.

    Anna Verdino / Giovanni Vigliotta / Deborah Giordano / Ivana Caputo / Annunziata Soriente / Margherita De Rosa / Anna Marabotti

    PLoS ONE, Vol 12, Iss 7, p e

    2017  Volume 0181563

    Abstract: We present the synthesis and biological evaluation of the prototype of a new class of cephalosporins, containing an additional isolated beta lactam ring with two phenyl substituents. This new compound is effective against Gram positive microorganisms, ... ...

    Abstract We present the synthesis and biological evaluation of the prototype of a new class of cephalosporins, containing an additional isolated beta lactam ring with two phenyl substituents. This new compound is effective against Gram positive microorganisms, with a potency similar to that of ceftriaxone, a cephalosporin widely used in clinics and taken as a reference, and with no cytotoxicity against two different human cell lines, even at a concentration much higher than the minimal inhibitory concentration tested. Additionally, a deep computational analysis has been conducted with the aim of understanding the contribution of its moieties to the binding energy towards several penicillin-binding proteins from both Gram positive and Gram negative bacteria. All these results will help us developing derivatives of this compound with improved chemical and biological properties, such as a broader spectrum of action and/or an increased affinity towards their molecular targets.
    Keywords Medicine ; R ; Science ; Q
    Subject code 540
    Language English
    Publisher Public Library of Science (PLoS)
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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  9. Article: An Anthracene-Incorporated [8]Cycloparaphenylene Derivative as an Emitter in Photon Upconversion

    Della Sala, Paolo / Amedeo Capobianco / Andrea Peluso / Carmen Talotta / Carmine Gaeta / Margherita De Rosa / Placido Neri / Tonino Caruso

    Journal of organic chemistry. 2018 Jan. 05, v. 83, no. 1

    2018  

    Abstract: The anthracene-incorporated [8]cycloparaphenylene 2 has been synthesized and its optoelectronic properties studied by UV–vis spectroscopy, cyclic voltammetry, and DFT calculations. NMR and computational studies indicate that the new cycloparaphenylene ... ...

    Abstract The anthracene-incorporated [8]cycloparaphenylene 2 has been synthesized and its optoelectronic properties studied by UV–vis spectroscopy, cyclic voltammetry, and DFT calculations. NMR and computational studies indicate that the new cycloparaphenylene derivative possesses a Cs point group symmetry. The new CPP 2 exhibits peculiar optoelectronic properties: (i) fluorescence emission is blue-shifted with respect to [8]cycloparaphenylene 1, and its quantum yield is higher; (ii) in the presence of an octaethylporphyrin Pd complex, as sensitizer, it undergoes a visible light upconversion. This is the first case in which a cycloparaphenylene derivative is involved as an emitter in low power light frequency conversion.
    Keywords chemical reactions ; chemical structure ; fluorescence ; nuclear magnetic resonance spectroscopy ; organic chemistry ; organic compounds ; photons ; ultraviolet-visible spectroscopy
    Language English
    Dates of publication 2018-0105
    Size p. 220-227.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.7b02590
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  10. Article ; Online: Calixpyrrole Derivatives

    Luca Valenti / Carmen Talotta / Annunziata Soriente / Margherita De Rosa / Franz H. Kohnke / Grazia Cafeo

    Molecules, Vol 14, Iss 7, Pp 2594-

    “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis

    2009  Volume 2601

    Abstract: Calix[4]pyrrole (1), calix[2]m-benzo[4]pyrrole (2), 10α,20β- and 10α,20α- bis(4-nitrophenyl)-calix[4]pyrroles 3 and 4, respectively, were found to exhibit various organocatalytic activities in the diastereoselective vinylogous addition reaction of 2- ... ...

    Abstract Calix[4]pyrrole (1), calix[2]m-benzo[4]pyrrole (2), 10α,20β- and 10α,20α- bis(4-nitrophenyl)-calix[4]pyrroles 3 and 4, respectively, were found to exhibit various organocatalytic activities in the diastereoselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF, 7) to aldehydes. The γ-hydroxybutenolide products are obtained in fairly good yields and with moderate diastereoselectivity. The structures of the catalysts, as well as the reaction conditions, strongly influence the efficiency of the reaction.
    Keywords calixpyrroles ; diastereoselective synthesis ; organocatalysis ; aldol addition ; 2-Trimethyl-silyloxyfuran ; Organic chemistry ; QD241-441
    Language English
    Publishing date 2009-07-01T00:00:00Z
    Publisher MDPI AG
    Document type Article ; Online
    Database BASE - Bielefeld Academic Search Engine (life sciences selection)

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