Monocyclic β-lactams as antibacterial agents: Facing antioxidant activity of N-methylthio-azetidinones

Cervellati, Rinaldo; Galletti, Paola; Greco, Emanuela; Cocuzza, Clementina; Musumeci, Rosario; Bardini, Luca; Paolucci, Francesco; Pori, Matteo; Soldati, Roberto; Giacomini, Daria

doi:10.1016/j.ejmech.2012.12.024

Cited by 18 publications

(22 citation statements)

References 36 publications

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“…Beside bicyclic β-lactam classes such as penicillins, cephalosporins and carbapenems, monocyclic compounds have emerged due to their interesting, variegated biological activities 25 . The efficacy evaluation against Staphylococcus aureus , including methicillin resistant strains (MRSA) of some monocyclic β-lactams with an alkylthio-group on the β-lactam nitrogen atom, has recently been reported 26–28 . Structure-activity relationship studies pointed out that the presence of a N -methylthio substituent proved to be essential for antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Monocyclic β-lactams loaded on hydroxyapatite: new biomaterials with enhanced antibacterial activity against resistant strains

Giacomini

Torricelli

Gentilomi

et al. 2017

Sci Rep

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The development of biomaterials able to act against a wide range of bacteria, including antibiotic resistant bacteria, is of great importance since bacterial colonization is one of the main causes of implant failure. In this work, we explored the possibility to functionalize hydroxyapatite (HA) nanocrystals with some monocyclic N-thio-substituted β-lactams. To this aim, a series of non-polar azetidinones have been synthesized and characterized. The amount of azetidinones loaded on HA could be properly controlled on changing the polarity of the loading solution and it can reach values up to 17 wt%. Data on cumulative release in aqueous solution show different trends which can be related to the lipophilicity of the molecules and can be modulated by suitable groups on the azetidinone. The examined β-lactams-HA composites display good antibacterial activity against reference Gram-positive and Gram-negative bacteria. However, the results of citotoxicity and antibacterial tests indicate that HA loaded with 4-acetoxy-1-(methylthio)-azetidin-2-one displays the best performance. In fact, this material strongly inhibited the bacterial growth of both methicillin resistant and methicillin susceptible clinical isolates of S. aureus from surgical bone biopsies, showing to be a very good candidate as a new functional biomaterial with enhanced antibacterial activity.

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Section: Introductionmentioning

confidence: 99%

Monocyclic β-lactams loaded on hydroxyapatite: new biomaterials with enhanced antibacterial activity against resistant strains

Giacomini

Torricelli

Gentilomi

et al. 2017

Sci Rep

Self Cite

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“…DHBA is selected as the monomer for grafting reaction since it is the inexpensive acid derivative that contains a catechol moiety (around $ 100 per kg and might be even cheaper in manufactural scale) . Since catechol could be easily oxidized in alkaline conditions, DHBA should be protected before use according to the literature . DMAP/DCC is a common catalyst system for esterification reaction, which is often used for further functionalizing the polymer, including PVA .…”

Section: Resultsmentioning

confidence: 99%

“…First, the t ‐butyldimethylsilyl (TBS)‐protected DHBA (DHBAT) was grafted onto the PVA backbone. DHBAT was synthesized according to the reported work . Specially, 2 g of PVA was added in 30 mL of CH 2 Cl 2 and stirred at room temperature until fully dissolved.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Adhesive Property Study of a Mussel-Inspired Adhesive Based on Poly(vinyl alcohol) Backbone

et al. 2017

Macromol. Chem. Phys.

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In this study, an effective way is presented to synthesize a mussel‐inspired adhesive from two inexpensive commercially available materials: polyvinyl alcohol (PVA) and 3,4‐dihydroxybenzoic acid via the esterification reaction and deprotection technology. This bioinspired adhesive exhibits good bonding ability on metal, glass, plastic, and wood, and the maximum bonding strength can be up to 4.0 MPa at dry conditions on glass substrate. Meanwhile, this adhesive can also be used as a wet/underwater adhesive. Such a PVA‐based bioinspired adhesive may be used as a potential candidate for applications in industrial field.

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“…The total antioxidant activity was determined measuring the phophomolybdenum blue complex with a maximum absorption at 695 nm [26]. The data, which are presented in Tables 2 and 3, showed that all the tested compounds are more active than ibuprofen.…”

Section: Total Antioxidant Activitymentioning

confidence: 99%

“…The total antioxidant activity of the tested compounds was evaluated using the phosphomolybdenum method according to the procedure in [26] with minor modifications. The method is based on the reduction of Mo(VI) to Mo(V) by the tested compounds followed by the formation of a green phosphate/Mo(V) complex at acid pH.…”

Section: Total Antioxidant Activitymentioning

confidence: 99%

Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

et al. 2014

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New thiazolidine-4-one derivatives of 2-(4-isobutylphenyl)propionic acid (ibuprofen) have been synthesized as potential anti-inflammatory drugs. The structure of the new compounds was proved using spectral methods (FR-IR, 1 H-NMR, 13 C-NMR, MS). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the total antioxidant activity, the DPPH and ABTS radical scavenging assays. Reactive oxygen species (ROS) and free radicals are considered to be involved in many pathological events like diabetes mellitus, neurodegenerative diseases, cancer, infections and more recently, in inflammation. It is known that overproduction of free radicals may initiate and amplify the inflammatory process via upregulation of genes involved in the production of proinflammatory cytokines and adhesion molecules. The chemical modulation of acyl hydrazones of ibuprofen 3a-l through cyclization to the corresponding thiazolidine-4-ones 4a-n led to increased antioxidant potential, as all thiazolidine-4-ones were more active than their parent acyl hydrazones and also ibuprofen. The most active compounds are the thiazolidine-4-ones 4e, m, which showed the highest DPPH radical scavenging ability, their activity being comparable with vitamin E.

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Monocyclic β-lactams as antibacterial agents: Facing antioxidant activity of N-methylthio-azetidinones

Cited by 18 publications

References 36 publications

Monocyclic β-lactams loaded on hydroxyapatite: new biomaterials with enhanced antibacterial activity against resistant strains

Monocyclic β-lactams loaded on hydroxyapatite: new biomaterials with enhanced antibacterial activity against resistant strains

Synthesis and Adhesive Property Study of a Mussel-Inspired Adhesive Based on Poly(vinyl alcohol) Backbone

Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

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