A Fluorinated Analogue of Marine Bisindole Alkaloid 2,2-Bis(6-bromo-1H-indol-3-yl)ethanamine as Potential Anti-Biofilm Agent and Antibiotic Adjuvant Against Staphylococcus aureus

Campana, Raffaella; Mangiaterra, Gianmarco; Tiboni, Mattia; Frangipani, Emanuela; Biavasco, Francesca; Lucarini, Simone; Citterio, Barbara

doi:10.3390/ph13090210

Cited by 12 publications

(8 citation statements)

References 37 publications

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“…Antibiotic adjuvants include: (1) anti-resistance drugs such as β-lactamase inhibitors pump inhibitors, membrane permeabilizers, and biofilm inhibitors; (2) antivirulence drugs, such as quorum-sensing inhibitors, toxin inhibitors, and secretion system inhibitors; (3) host-directed therapies such as innate immune system agonists and immunomodulatory peptides; and (4) other therapies such as phage, probiotic, and oral rehydration therapies ( Gill et al, 2015 ). Various synthetic and natural compounds such as prazolopyridazine derivatives ( Schaenzer et al, 2018 ), isoflavonoids ( Abreu et al, 2017 ), plant extracts ( Abreu et al, 2016 ), cationic peptides ( Geitani et al, 2019 ), cannabidiol ( Wassmann et al, 2022 ), marine bisindole alkaloid ( Campana et al, 2020 ), cinnamonitrile ( Speri et al, 2019 ), amine oxide alkyl derivatives ( Fagnani et al, 2021 ), and brominated carbazoles ( Berndsen et al, 2022 ) have been recently proposed to be used as antibiotic adjuvants against S. aureus strains.…”

Section: Discussionmentioning

confidence: 99%

Fatty Acids as Aminoglycoside Antibiotic Adjuvants Against Staphylococcus aureus

et al. 2022

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Fatty acids have diverse functions in the vast majority of cells. At high doses, they act as antimicrobials while, at low doses, they exhibit antibiofilm and antivirulence activities. In this study, the synergistic antibacterial and antibiofilm activities of 30 fatty acids and 11 antibiotics were investigated against methicillin-sensitive and methicillin-resistant Staphylococcus aureus strains. Of the 15 saturated and 15 unsaturated fatty acids examined, 16 enhanced the antibacterial activity of tobramycin. Combinatorial treatment with myristoleic acid (the most active) at 10 μg/ml and tobramycin at 10 μg/ml decreased cell survival by >4 log as compared with tobramycin treatment alone. Notably, aminoglycoside antibiotics, such as tobramycin, kanamycin, gentamicin, and streptomycin exhibited antimicrobial synergy with myristoleic acid. Co-treatment with myristoleic acid and antibiotics markedly decreased biofilm formation. Interestingly, co-treatment with tobramycin and myristoleic acid induced a reduction in S. aureus cell size. These results suggest that fatty acids, particularly myristoleic acid, can be used as aminoglycoside antibiotic adjuvants against recalcitrant S. aureus infections.

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Section: Discussionmentioning

confidence: 99%

Fatty Acids as Aminoglycoside Antibiotic Adjuvants Against Staphylococcus aureus

et al. 2022

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“…Since the 2,2‐bis(6‐bromo‐3‐indolyl) ethanamine targets anti‐apoptotic Bcl‐2 protein and, consequently, can have success in killing many types of cancer, its chemical structure can be considered the basic scaffold to obtain synthetic derivatives with similar biological properties but with an improved chemical stability (Imran et al, 2015). Synthetic derivative activities as antimicrobial molecules and, in particular, compound 1 as antibiofilm agent, have been previously described (Campana et al, 2019; Campana et al, 2020). Here, the anti‐cancer potential action of three bisindole alkaloid derivatives has been evaluated.…”

Section: Discussionmentioning

confidence: 99%

Morpho‐functional analyses reveal that changes in the chemical structure of a marine bisindole alkaloid alter the cytotoxic effect of its derivatives

Burattini

Battistelli

Verboni

et al. 2022

Microscopy Res & Technique

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2,2-bis(6-bromo-1H-indol-3-yl) ethanamine, a marine bisindole alkaloid, showed anticancer property in several tumor cell lines thanks to the presence of a 3,3 0diindolylmethane scaffold. Here, the modifications in its chemical structure into alkaloid-like derivatives, have been evaluated, to investigate changes in its biological activities. Three derivatives have been considered and their potential apoptotic action has been evaluated through morpho-functional analyses in a human cancer cell line. Apoptosis appears strongly decreased in the derivatives without the bromine atoms (1) and in those where the bromine atoms have been substituted with fluorine atoms (2). On the contrary, the methylation of indole NH (3) does not alter the alkaloid apoptotic activity that occurs through mitochondria involvement supported by cardiolipin peroxidation and dysfunctional mitochondria presence. This manuscript highlights the alkaloid derivative cytotoxic effect, which is strictly correlated to the presence of N-methylated bisindole alkaloid and bromine atoms, conditions which assure to maintain the pro-apoptotic activity. Since molecular therapies, by targeting mitochondria pathways, have shown positive outcomes against several cancer cells, the alkaloid with bisindole methylated scaffold and the two bromine atoms can be considered a promising candidate to develop new derivatives with strong anticancer property.anticancer activity, apoptotic cell death, marine alkaloids, mitochondria damage, U937 cell line Research Highlights• 2,2-bis(6-bromo-1H-indol-3-yl) ethanamine is an alkaloid known for its anticancer properties.• Morpho-functional analyses evaluated cytotoxicity of its synthetic derivatives in tumor cells.• Anticancer properties depend on the presence of bisindole scaffold and the two bromine units.Marine bisindole alkaloids showed significant cytotoxicity, antineoplastic and antimicrobial properties (Kamel et al., 2020; Veale & Davies-Coleman, 2014). In particular, 2,2-bis(6-bromo-3-indolyl) ethanamine (BrDIMEA), extracted from the Californian tunicate Didemnum candidum and the New Caledonian sponge Orina (Salucci et al., 2018), is a strong cytotoxic agent and its anticancer

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“…Nine studies did not indicate information on extraction sources due to purchasing from material companies (Campana et al, 2020;Guo et al, 2021;Johnson et al, 2020;Li et al, 2021;Özdoğan et al, 2021;Ribeiro-Vidal et al, 2020;Tang et al, 2022;Xu et al, 2020;Zhou et al, 2021). One of these studies fabricated doxycycline-containing chitosan/carboxymethyl chitosan nanoparticles (Dox:CS/CMCS-NPs) and evaluated several biological activities, including antibacterial, anti-inflammatory, and cell proliferative activities (Xu et al, 2020).…”

Section: Fisheries and Aquatic Sciencesmentioning

confidence: 99%

Therapeutic effect of marine bioactive substances against periodontitis based on in vitro, in vivo, and clinical studies

Lee¹,

Kwon²,

Jung³

2023

Fish Aquat Sci

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Marine bioactive substances (MBS), such as phlorotannins, collagens, peptides, sterols, and polysaccharides, are increasing attention as therapeutic agents for several diseases due to their pharmacological effects. Previous studies have demonstrated the biological activities of MBS including antibacterial, anticoagulant, antidiabetic, antimicrobial, anti-inflammatory activities. Among numerous human diseases, periodontitis is one of the high-prevalence inflammatory diseases in the world. To treat periodontitis, several surgeries (bone grafting, flap surgery, and soft tissue graft) are usually used. However, the surgery for patients with chronic periodontitis induces several side effects, including additional inflammatory responses at the operated site, chronic wound healing, and secondary surgery. Therefore, this review assessed the most recent trends in MBS using Google Scholar, PubMed, and Web of Science search engines to develop marine-derived therapeutic agents for periodontitis. Further, we summarized the current applications and therapeutic potential of MBS to serve as a reference for developing novel technologies applied to MBS against periodontitis treatment.

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A Fluorinated Analogue of Marine Bisindole Alkaloid 2,2-Bis(6-bromo-1H-indol-3-yl)ethanamine as Potential Anti-Biofilm Agent and Antibiotic Adjuvant Against Staphylococcus aureus

Cited by 12 publications

References 37 publications

Fatty Acids as Aminoglycoside Antibiotic Adjuvants Against Staphylococcus aureus

Fatty Acids as Aminoglycoside Antibiotic Adjuvants Against Staphylococcus aureus

Morpho‐functional analyses reveal that changes in the chemical structure of a marine bisindole alkaloid alter the cytotoxic effect of its derivatives

Therapeutic effect of marine bioactive substances against periodontitis based on in vitro, in vivo, and clinical studies

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