Synthesis and Biological Properties of Alkyl Esters of Polyene Antibiotics

Bruzzese, T.; Cambieri, M.; Recusani, F

doi:10.1002/jps.2600640327

Cited by 38 publications

(15 citation statements)

References 4 publications

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“…In vitro studies against S. cerevisiae and in vivo studies against C. albicans in mice confirmed previous findings that polyene macrolide ester salts are at least as biologically active as their parent antibiotics and in some cases even more active (Bonner et al, 1972). Bruzzese et al (1975) findings agreed with Bonner's, but also observed that the lengthening of the aliphatic chain in the ester group (methyl to butyl) produced a gradual decrease in activity. Bonner et al (1972) also examined the acute intraperitoneal toxicities of polyene macrolides and their methyl ester hydrochlorides in mice.…”

Section: Carboxyl Group Derivativessupporting

confidence: 91%

“…More comprehensive studies were performed examining the biological properties of polyene macrolide ester salts (Bonner et al, 1972;Bruzzese et al, 1975). In vitro studies against S. cerevisiae and in vivo studies against C. albicans in mice confirmed previous findings that polyene macrolide ester salts are at least as biologically active as their parent antibiotics and in some cases even more active (Bonner et al, 1972).…”

Section: Carboxyl Group Derivativesmentioning

confidence: 63%

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Comparative Study of a Semisynthetic Derivative of Natamycin and the Parent Antibiotic on the Spoilage of Shredded Cheddar Cheese

Suloff

Marcy

Hackney

et al. 2003

Journal of Food Protection

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The polyene macrolide antibiotic natamycin (Antibiotic A-5283) is commonly used to retard the growth of surface molds on various cheese varieties. Natamycin is commonly applied to the surface of cheese by dipping or spraying, using an aqueous dispersion containing 200 to 300 ppm of the additive. The large molecular weight of natamycin, 666 g/mol, and conjugated double bond structure causes it to be extremely insoluble in water and most food grade solvents. The inability to apply natamycin in true solution creates void non-treated areas on the food surface. These non-treated areas promote the growth of fungal organisms.A water soluble N-alkyl semisynthetic derivative of natamycin was synthesized by the Michael addition reaction of the parent with a N-substituted malemide. A comparative study investigating the effectiveness of the semisynthetic derivative of natamycin and the parent antibiotic in suppressing mold growth on one month aged shredded Cheddar cheese modified atmosphere packaged (MAP) was performed. A 20 ppm natamycin treatment effectively suppressed visible mold growth (<10 4 CFU/g) in MAP samples for up to 30 days after opening. The 20 ppm semisynthetic derivative performed similarly to the 10 ppm natamycin treatment in retarding mold growth. Visible mold growth did not occur for these treatments in MAP samples until 20 days after opening. Analysis of storage conditions revealed that an outgrowth of mold in shredded cheese occurred in MAP packages stored longer than 15 days. This bloom in mold growth was attributed to the degradation of natamycin and the semisynthetic derivative throughout storage.The stability and degradation of natamycin and the derivative were monitored throughout the study. Antibiotic concentration on the cheese surface was quantified by molecular absorption spectrometry. Results from this study showed, heavily contaminated samples caused the rate and loss of natamycin and the derivative to increase. Antibiotic concentration decreased at a similar rate in MAP and open package conditions. Natamycin and derivative were found to have similar degradation properties.iii DEDICATION This thesis is dedicated to my wife, Amy Lynn Suloff. I cannot express in words the love and support Amy provided during this project. For these endearing qualities, and so many more I want to thank her. iv ACKNOWLEDGMENTS

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Section: Carboxyl Group Derivativessupporting

confidence: 91%

Section: Carboxyl Group Derivativesmentioning

confidence: 63%

Comparative Study of a Semisynthetic Derivative of Natamycin and the Parent Antibiotic on the Spoilage of Shredded Cheddar Cheese

Suloff

Marcy

Hackney

et al. 2003

Journal of Food Protection

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“…Amphotericin B methyl ester (AME), the water-soluble derivative of AMB, has been shown in experimental animals to be significantly less toxic than the parent compound (6) and to be effective in the treatment of certain experimental fungal infections (1,8). Although systemic candidiasis is likely to be a major indication for AME therapy once approved for human use, there is little published information on the in vitro susceptibility of Candida albicans to this antibiotic (2,5,9). We report the comparative susceptibility of 465 clinical isolates of C. albicans to AMB and AME.…”

mentioning

confidence: 99%

Comparative Susceptibility of Candida albicans to Amphotericin B and Amphotericin B Methyl Ester

Bannatyne

Cheung

1977

Antimicrob Agents Chemother

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The in vitro antifungal activities of amphotericin B (AMB) and amphotericin B methyl ester (AME) were compared against 465 clinical isolates of Candida albicans. AMB and AME possessed comparable activity against half of the strains, but against the remainder of the strains the activity of AME was slightly lower than that of AMB. Rarely did AME show superior antifungal activity to AMB.Amphotericin B (AMB) is the most effective antibiotic currently available for the treatment of serious fungal infections in humans. Its usefulness is hampered by its nephrotoxicity and other side effects (4,7,10,11). Amphotericin B methyl ester (AME), the water-soluble derivative of AMB, has been shown in experimental animals to be significantly less toxic than the parent compound (6) and to be effective in the treatment of certain experimental fungal infections (1,8). Although systemic candidiasis is likely to be a major indication for AME therapy once approved for human use, there is little published information on the in vitro susceptibility of Candida albicans to this antibiotic (2, 5, 9). We report the comparative susceptibility of 465 clinical isolates of C. albicans to AMB and AME.MATERIALS AND METHODS Cultures. Four hundred and sixty-five C. albicans isolates, each from a different patient, were obtained from a variety of clinical sources. Duplicate or triplicate isolates of49 of these strains were available and tested. All isolates were identified by germ tube production, sugar fermentation pattern, and carbohydrate assimilation tests with sucrose. Isolates were maintained on nutrient agar slants at 22°C. Before testing, strains were grown on 5% horse blood agar plates for 20 to 40 h at 37°C. Cells were harvested with sterile normal saline, and the turbidity of the suspension was adjusted to a standard transmission of 90% at 530 nm on a Spectronic 20 spectrophotometer (Bausch and Lomb).Media. The susceptibility tests were performed in a solid synthetic medium (5). The medium was dispensed in 350-ml quantities into 1-liter Erlenmeyer flasks and sterilized by autoclaving. AMB or AME was added to the melted agar, mixed well, and dispensed into sterile square petri dishes (100 by 15 mm, integrid; Falcon Plastics). Plates were cooled, stored at 4°C in the dark, and used within 48 h.Preparation of antibiotic dilutions. A 5.0-mg amounit of AMB or AME (E. R. Squibb and Sons, Inc.) was dissolved in 5 ml of sterile dimethyl sulfoxide and diluted with sterile distilled water to obtain stock solutions containing from 200 to 6.25 ,ug/ml. A 3.5-ml portion of the latter or sterile distilled water was added to each flask containing 350 ml of molten agar to produce final concentrations of AMB or AME of 0, 0.0625, 0.125, 0.25, 0.5, 1.0, and 2.0 ug/ml of medium. Susceptibility testing. Standardized cell suspensions of C. albicans were inoculated onto the agar plates by using a Steers replicator. Plates were incubated at 37°C in the dark and read after 48 and 72 h. Complete absence of growth in at least two of three test cultures was considere...

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“…The functional integrity of the PMN is thus a requirement for elimination of Candida, and drugs to be used in topical or systemic therapy should not inhibit these phagocytic cells. With this in mind we have studied the possible effects of the polyene antibiotic mepartricin (Bruzzese, Cambieri and Recusani, 1975), which is active against Trichomonas and Candida, on PMN functions in vitro. Like other polyene antibiotics, mepartricin interacts with the sterols present in cell membranes (Pellegrini, Ruozi and De Bernardi, 1974) causing a rapid drop in oxygen consumption by fungal cells (Ritzerfeld, 1972) and changes in the external layers of the cell wall (Ruozi, Zara and Pellegrini, 1974).…”

Section: T H E Effects O F T H E Polyene Antibiotic M E P a R T R I Cmentioning

confidence: 99%

The Effects of the Polyene Antibiotic Mepartricin on Polymorphonuclear Leucocyte Function: An In-Vitro Study

Sacchi

Cuviot

Ferrari

et al. 1979

Journal of Medical Microbiology

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Synthesis and Biological Properties of Alkyl Esters of Polyene Antibiotics

Cited by 38 publications

References 4 publications

Comparative Study of a Semisynthetic Derivative of Natamycin and the Parent Antibiotic on the Spoilage of Shredded Cheddar Cheese

Comparative Study of a Semisynthetic Derivative of Natamycin and the Parent Antibiotic on the Spoilage of Shredded Cheddar Cheese

Comparative Susceptibility of Candida albicans to Amphotericin B and Amphotericin B Methyl Ester

The Effects of the Polyene Antibiotic Mepartricin on Polymorphonuclear Leucocyte Function: An In-Vitro Study

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