Mechanism of Action of Dipropofol and Synergistic Action with Other Antibacterial Agents in Vitro

Ogata, Masahiro; Kunikane, Takao; Seki, Masako; Oka, Kentaro; Urano, Shiro; Seki, Syûzô; Seki, Yasuhide; Endō, Toyoshige

doi:10.1248/bpb.28.1773

Cited by 4 publications

(3 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synergy against VRE was only confirmed with the combination between dipropofol and rifampicin. 15) To our knowledge, this is the first study describing the enhancing activity of ascorbic acid to the antimicrobial compound, and in the presence of ascorbic acid dipropofol was solubilized in water, stable to air oxidation and showed synergistic potency against Gram-positive and Gramnegative bacteria. In conclusion, we could offer a new route for the development of solubilzing lipophilic compounds, which was abandoned due to strong lipohilicity.…”

Section: Resultsmentioning

confidence: 85%

Solubilization of Dipropofol, an Antibacterial Agent, Using Saccharide and Ascorbic Acid

Ogata

Oka

Seki

et al. 2007

Biological & Pharmaceutical Bulletin

Self Cite

View full text Add to dashboard Cite

For more than 30 years, vancomycin has been a reliable treatment for Gram-positive bacterial infection. Injectable forms of vancomycin were introduced, and have been used exclusively for methicillin-resistant Staphylococcus aureus (MRSA) infection. Recently, the MRSA strain, which contains the vanA gene, with high resistance to vancomycin (MIC Ͼ128 mg/ml) has been reported in clinical isolates. 1,2)The emergence of vancomycin resistant bacterial strains is a very serious public health problem. Therefore, a new anti-MRSA antibiotic is clinically of interest. Dipropofol ( Fig. 1) was recognized as an oxidative dimerization metabolite of propofol (2,6-diisopropylphenol), a novel sedative and anesthetic agent having antioxidant activity, but not antibacterial activity.3,4) Dipropofol was investigated to have a higher antioxidant activity than that of propofol, and to show potent antibacterial activity against Grampositive strains including MRSA and vancomycin resistant Enterococci (VRE). 4,5) However, the insolubility of dipropofol in water could be plausible for its efficacy and application fields. Consequently, the solubilization of dipropofol in water was a next target. To obtain the water-solubility of the compounds, many researchers have used synthetic approaches and selected suitable derivatives.6,7) However, we selected another method of adding other types of compounds, expecting complex formations and synergistic activity with the additions. MATERIALS AND METHODSChemicals Dextrose anhydrous, saccharose, ascorbic acid and lecithin (from egg) were purchased from the Wako Pure Chemical Co. (Osaka, Japan). D(Ϫ)-Fructose, D(ϩ)-mannose, D(ϩ)-xylose, maltose monohydrate, and D-sorbitol were purchased from Sigma-Aldrich Japan K.K. (Tokyo, Japan). Dipropofol was synthesized by the method reported previously. 4)Antimicrobial Susceptibility The disk-diffusion test, using S. aureus 209P and E. coli JCM5491 (ATCC25922) was applied to determine the antimicrobial activity of the test compounds. The test organisms were grown overnight at 37°C by shaking in a TSB medium and the aliquots (100 ml) were streaked onto trypticase soy agar plates. A dipropofol solution (1 mg/ml in methanol) was suspended with saccharide (1 g) or ascorbic acid (1 g). The perfect removal of methanol produced a dipropofol complex with saccharide or ascorbic acid, which dissolved in distilled water (5 ml). For plate diffusion tests, 50 ml of the test compound was dropped on paper disks (diameter 8 mm), which were dried under sterile conditions and put on and an agar plate inoculated with the test organism. The plates were cultivated at 37°C for 24 h. Combination Study and Synergism DeterminationThe in vitro combinational effect of the dipropofol with ascorbic acid was examined by the checkerboard titration method. Overnight a culture of S. aureus, grown in 10 ml of Mueller-Hinton broth at 37°C, was diluted 10 3 -fold with fresh Mueller-Hinton broth, followed by the addition of S. aureus (about 5ϫ10 4 CFU) onto 20 ml Mueller-Hinton agar layers which co...

show abstract

Section: Resultsmentioning

confidence: 85%

Solubilization of Dipropofol, an Antibacterial Agent, Using Saccharide and Ascorbic Acid

Ogata

Oka

Seki

et al. 2007

Biological & Pharmaceutical Bulletin

Self Cite

View full text Add to dashboard Cite

show abstract

“…We also know previous reports that the resin oils contain the ammonium and benzoic acid, a phenolic type that is antioxidant and oxidative. So far, there is no study that can give us a clear and accurate idea of the work of essential oils, so it is very likely that each component of essential oils have a special mechanism of action, and takes its work in three stages: (i) Attack essential bacterial wall oils, causing increased permeability and loss of cellular components, (ii) Acidification within the cell, disrupting cellular energy production and (iii) Destruction of genetic material, resulting in the death of bacteria [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27].…”

Section: Antibacterial Activitymentioning

confidence: 99%

Evaluation of antibacterial and antioxidant activities of three types of benzoin resin

et al. 2018

View full text Add to dashboard Cite

The benzoin resin is used extensively in traditional medicine for its many reported therapeutic properties. The essential oils of three different types of benzoin resin were extracted using the traditional method in this study. The yield of essential oils of the white, red and gray types of resin was 1.01, 0.92 and 0.54%, respectively. The obtained extracts were tested against two types of pathogenic bacteria, Staphylococcus aureus and Escherichia coli. The tests showed that essential oil of gray type resin is effective against both Escherichia coli (14 mm) and Staphylococcus aureus (11 mm). The antioxidant activity has been also evaluated to compare the efficiency of different type of resin with DPPH· assay. In the DPPH· system, the antioxidant activity of the red resin extract (0.01 μg/mL) was superior to that of the white (27.32 μg/mL) and gray (42.90 μg/mL) extracts, with IC50 values, respectively.

show abstract

“…We concluded that the mode of action of dipropofol was mediated by inhibition of protein synthesis or an amino acid incorporation system. 14) However, interaction of the hydroxyl group, isopropyl group, and dimeric skeleton in the expression of antibacterial activity is not clear. Based on the evidence, it was suggested that dipropofol seems to be a useful compound for a hospital infection such as Linezolid, because of its strong antibacterial activity against VRE and MRSA.…”

Section: )mentioning

confidence: 99%

Antibacterial Activity of Dipropofol and Related Compounds

Ogata

Sato

Kunikane

et al. 2005

Biological & Pharmaceutical Bulletin

Self Cite

View full text Add to dashboard Cite

Phenolic compounds, in general, exhibit antioxidant and antibacterial activities. We studied antimicrobial activity of the phenolic antioxidants, propofol (2,6-diisopropylphenol), tocopherol, eugenol, butylated hydroxyanisole (BHA), and several of their dimer compounds. Dipropofol (dimer of 2,6-diisopropylphenol) showed strong antibacterial activity against gram-positive strains including methicillin resistant Staphylococcus aureus (MRSA) and vancomycin resistant Enterococci (VRE), while propofol and other monomeric and dimeric phenols having methyl or tert-butyl groups showed no remarkable activity. The results indicated that the dimeric structure of 2,6-diisopropylphenol moiety may play an important role in the antibacterial activity.

show abstract

Mechanism of Action of Dipropofol and Synergistic Action with Other Antibacterial Agents in Vitro

Cited by 4 publications

References 14 publications

Solubilization of Dipropofol, an Antibacterial Agent, Using Saccharide and Ascorbic Acid

Solubilization of Dipropofol, an Antibacterial Agent, Using Saccharide and Ascorbic Acid

Evaluation of antibacterial and antioxidant activities of three types of benzoin resin

Antibacterial Activity of Dipropofol and Related Compounds

Contact Info

Product

Resources

About