Syntheses and anti-MRSA activities of the C3 analogs of mansonone F, a potent anti-bacterial sesquiterpenoid: insights into its structural requirements for anti-MRSA activity

Shin, Dongyun; Kim, Sun Nam; Chae, Junghyun; Hyun, Soonsil; Seo, Sang Woo; Lee, Yong‐Sil; Lee, Kwang-Ok; Kim, Seokho; Lee, Yun Sang; Jeong, Jae Min; Choi, Nam-Song; Suh, Young‐Ger

doi:10.1016/j.bmcl.2004.06.039

Cited by 40 publications

(9 citation statements)

References 13 publications

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“…However, some Staphylococcus strains resistant to glycopeptides have been reported in Brazil [ 11 ] and other countries [ 12 ]. Then, the research on new antimicrobial agents is an area of great importance [ 5 , 13 ].…”

Section: Introductionmentioning

confidence: 99%

Tabebuia avellanedae naphthoquinones: activity against methicillin-resistant staphylococcal strains, cytotoxic activity and in vivo dermal irritability analysis

Pereira

Machado

Leal

et al. 2006

Ann Clin Microbiol Antimicrob

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BackgroundMethicillin-resistant Staphylococcus aureus (MRSA) and coagulase-negative staphylococcus infections are a worldwide concern. Currently, these isolates have also shown resistance to vancomycin, the last therapy used in these cases. It has been observed that quinones and other related compounds exhibit antibacterial activity. This study evaluated the antibacterial activity, toxicity and in vivo dermal irritability of lapachol extracted from Tabebuia avellanedae and derivatives against methicillin-resistant staphylococcal isolates. In addition, its mechanism of action was also analyzed.MethodsThe compounds β-lapachone, 3-hydroxy β N lapachone and α-lapachone were tested to determine the MIC values against methicillin-resistant S. aureus, S. epidermidis and S. haemolyticus strains, being the two last ones hetero-resistant to vancomycin. Experiments of protein synthesis analysis to investigate the naphthoquinones action were assessed. In vitro toxicity to eukaryotic BSC-40 African Green Monkey Kidney cell cultures and in vivo primary dermal irritability in healthy rabbits were also performed.ResultsThe compounds tested showed antibacterial activity (MICs of 8, 4/8 and 64/128 μg/mL to β-lapachone, 3-hydroxy β N lapachone and α-lapachone, respectively), but no bactericidal activity was observed (MBC > 512 μg/mL for all compounds). Although it has been observed toxic effect in eukaryotic cells, the compounds were shown to be atoxic when applied as topic preparations in healthy rabbits. No inhibition of proteins synthesis was observed.ConclusionOur results suggest that quinones could be used in topic preparations against wound infections caused by staphylococci, after major investigation of the pharmacological properties of the compounds. Studies about the use of these compounds on tumoral cells could be carried on, due to their effect in eukaryotic cells metabolism.

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Section: Introductionmentioning

confidence: 99%

Tabebuia avellanedae naphthoquinones: activity against methicillin-resistant staphylococcal strains, cytotoxic activity and in vivo dermal irritability analysis

Pereira

Machado

Leal

et al. 2006

Ann Clin Microbiol Antimicrob

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“…The orthoquinone structure was reported to be essential for the anti-methicillin-resistant S. aurens (MRSA) activity of the sesquiterpenoid quinone, mansonone. 12 However, for antifungal activity, we found that paraquinone was more potent than orthoquinone. Furthermore, the MIC values of thymoquinone and menadione were not reversed by the addition of excess d-cysteine (data not shown).…”

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confidence: 97%

Evaluation of the effect of terpenoid quinones on Trichophyton mentagrophytes by solution and vapor contact

Inouye

Uchida²,

Takizawa

et al. 2006

Journal of Infection and Chemotherapy

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“…The MICs of the test compounds and the standard control drugs are tabulated in Table 2. (1). Though this conversion has already been effected in glacial acetic acid under reflux [12], it is now found that the reaction takes place smoothly in water medium without the aid of the acid.…”

Section: In Vitro Antibacterial Activitymentioning

confidence: 91%

“…The synthesized compounds were purified by column chromatography using column silica gel 100-200 mesh (ethyl acetate/hexane 1:2). All the compounds were characterized by UV-Vis spectrophotometer (UV-1800, Shimadzu, Japan) using acetone as solvent, FT-IR spectrometer (IR 8400, Shimadzu, Japan) using KBr pellets, 1 H NMR spectroscopy in DMSO (400 MHz, Bruker), 13 C NMR spect r o s c o p y i n D M S O ( 1 0 0 M H z , B r u k e r ) u s i n g tetramethylsilane (TMS) as internal standard. Coupling constants (J values) are reported in hertz.…”

Section: Methodsmentioning

confidence: 99%

“…The vancomycin and teicoplanin of glycopeptide antibiotics, quinupristin/ dalfopristin, and linezolid of new antibiotics are clinically identified and used for the treatment of MRSA infections, but the structural complexity and side effects of these antibiotics have prompted increased efforts to develop novel antibiotics. Thus, the discovery and development of new classes of antibacterial drugs are essentially of great concern due to the rapid acquirement of multidrug resistance by Grampositive and Gram-negative pathogens [1].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, molecular docking and antibacterial evaluation of new 1,4-naphthoquinone derivatives contains carbazole-6,11-dione moiety

2014

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A new series of new 1,4-naphthoquinone derivatives containing carbazole-6,11-dione moiety, which has not been reported yet, has been synthesized from 1,4-naphthoquinone and 4-aminophenylsulfone involving a Michael addition, benzoylation, and Pd-catalyzed coupling. This set of compounds has been evaluated for in vitro antibacterial studies against different Gram-positive and Gramnegative bacteria, and most of the synthesized compounds exhibited good antibacterial activity and the minimum inhibitory concentrations (MICs) are compared with the standard drugs used. Compound 7 exhibited good antibacterial activity among all the molecules studied with the best MIC of 2.1 μg/ mL against Bacillus subtilis. To understand the molecular interactions with targeted proteins, the molecular docking of all the synthesized compounds were carried out; between 14 molecules docked, compound 7 was the one with the best glide and E model score of −7.73 and −95.37, respectively. In all docked molecules, compound 5 exhibited least glide and E model score of −4.55 and −101.56, respectively.

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Syntheses and anti-MRSA activities of the C3 analogs of mansonone F, a potent anti-bacterial sesquiterpenoid: insights into its structural requirements for anti-MRSA activity

Cited by 40 publications

References 13 publications

Tabebuia avellanedae naphthoquinones: activity against methicillin-resistant staphylococcal strains, cytotoxic activity and in vivo dermal irritability analysis

Tabebuia avellanedae naphthoquinones: activity against methicillin-resistant staphylococcal strains, cytotoxic activity and in vivo dermal irritability analysis

Evaluation of the effect of terpenoid quinones on Trichophyton mentagrophytes by solution and vapor contact

Synthesis, molecular docking and antibacterial evaluation of new 1,4-naphthoquinone derivatives contains carbazole-6,11-dione moiety

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