Physicochemical properties of vancomycin and iodovancomycin and their complexes with diacetyl-<scp>l</scp>-lysyl-<scp>d</scp>-alanyl-<scp>d</scp>-alanine

Nieto, Manuel; Perkins, H. R.

doi:10.1042/bj1230773

Cited by 171 publications

(94 citation statements)

References 11 publications

(5 reference statements)

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“…Vancomycin interferes with cell wall synthesis by combining with the D-alanine residues of the peptidoglycan chain and preventing the cross-link required for stable cell wall synthesis, thus being bactericidal against dividing microbes. [30][31][32] Gentamicin, on the other hand, is an aminoglycoside which inhibits protein synthesis by binding to the 30S subunit of the ribosome. 33,34 Therefore, vancomycin has a direct effect on the cell wall, whereas gentamicin is thought to have an indirect effect on the development and integrity of the cell membrane.…”

Section: Discussionmentioning

confidence: 99%

Distinction between intact and antibiotic‐inactivated bacteria by real‐time PCR after treatment with propidium monoazide

Kobayashi

Oethinger

Tuohy

et al. 2010

Journal Orthopaedic Research

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One limitation to the use of the polymerase chain reaction (PCR) to identify orthopedic infections has been apparent falsepositive results, possibly due to the detection of dead bacteria. We recently showed that the use of DNA-binding agent propidium monoazide (PMA) could distinguish viable from heat-inactivated bacteria, and, in this study, we investigated whether the same technique can be applied to bacteria killed by two antibiotics with distinctly different mechanisms of action, a test of greater clinical relevance than thermal inactivation. Staphylococcus aureus and S. epidermidis were inactivated by vancomycin and gentamicin and treated with PMA or left untreated before DNA extraction. The threshold cycle difference of antibiotic-treated bacteria with and without PMA pretreatment was investigated with PCR primers for the 16S rDNA and tuf genes. Our results indicated that PMA effectively inhibited detection by PCR of bacteria, which had been inactivated by either vancomycin or gentamicin. The effect was statistically significant at 24 h after treatment (C t difference consistently >3; p < 0.05) and after 10 days of treatment (C t difference >4; p < 0.01), when compared to viable cells (C t difference 1-2). Vancomycin had a stronger effect on the C t value than gentamicin, reflecting the different mechanism of action of each antibiotic. Techniques of this type may help reduce clinically false-positive PCR results caused by the detection of dead bacteria, and may be especially useful in patients who have received antibiotics, such as patients undergoing the second stage of a two-stage revision for infected arthroplasty. ß

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Section: Discussionmentioning

confidence: 99%

Distinction between intact and antibiotic‐inactivated bacteria by real‐time PCR after treatment with propidium monoazide

Kobayashi

Oethinger

Tuohy

et al. 2010

Journal Orthopaedic Research

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“…Somma et al (1984) reported that teicoplanin, like vancomycin (Best & Durham, 1965;Nieto & Perkins, 1971), binds to cell walls and forms a complex with peptides related to bacterial peptidoglycan, such as…”

Section: Inhibition Of' Teicoplanin-induced Lysis By the Peptide Ac-lmentioning

confidence: 99%

Bacteriolytic effect of teicoplanin

Chmara

Ripa

Mignini

et al. 1991

Journal of General Microbiology

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The glycopeptide antibiotic teicoplanin belongs to the same group as vancomycin and ristocetin and is a valuable tool for studying the autolytic system of sensitive Gram-positive bacteria. Teicoplanin, at a concentration of 1 pg ml-I, caused rapid lysis of exponential phase cells of Streptococcus faecafis. Baciffus spp. were most sensitive to the antibiotic; effective lysis occurred at 0.1 pg teicoplanin ml-l . The bacteriolytic effect depended on the antibiotic concentration, the growth phase and growth rate of the target organism. Antibiotic added to overnight cultures did not cause lysis. Mgz+ (50 mM) was unable to prevent lysis. Mutants with decreased autolytic activity were more resistant to teicoplanin and lysed more slowly than the wild-type. Growth of bacteria in slightly acidic medium protected the cells against the lytic effect of teicoplanin typically observed at pH 7 or 8. This pH-dependent antibiotic tolerance was demonstrated with both bacilli and streptococci. Bacterial lysis was prevented by the presence of Ac-L-Lys(Ac)-D-Ala-D-Ala and normal growth was observed when this peptide was added simultaneously with teicoplanin. Bacteria pretreated with teicoplanin, washed and transferred to fresh medium or buffers behaved as if the antibiotic was still present; in neutral or slightly alkaline conditions strong lysis occurred, whereas in acidic buffer only bacteriostasis was observed. In contrast to vancomycin, teicoplanin induced some lysis of bacteria in hypertonic media, presumably by affecting the integrity of the cell membrane.

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“…Their structure elucidation therefore presents an interesting challenge to current methods, especially since some aspects of the molecular basis for their physiological action are known (Refs. 31,32). …”

Section: Structural Studies On Glycopeptide Antibioticsmentioning

confidence: 99%

Structural and sequencing studies on peptides, proteins, and glycopeptide antibiotics by mass spectrometry

Williams¹

1978

Pure and Applied Chemistry

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-Mass spectrometry is now established as a useful method for establishing the sequence of small peptides (2-10 residues), following their derivatisation (by N-acetylation and permethylation) to increase volatility.The strength of the method lies in its ability to deal with simple mixtures of peptides and to identify unusual amino acids.The weakness of the method (relative to some wet-chemical approaches to sequencing) lies in the current inability of the method to sequence larger peptides, and the relatively low sensitivity when working with peptides near the molecular weight limit of the method.This last shortcoming is due to our present inability to volatilise and efficiently produce high mass ions from the larger peptides, the inherent sensitivity of mass spectrometry being in contrast extremely high.The use of deuterated reagents in degradation and derivatisation reactions provides a powerful method for structure elucidation of glycopeptide antibiotics containing unusual amino acids.

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Physicochemical properties of vancomycin and iodovancomycin and their complexes with diacetyl-l-lysyl-d-alanyl-d-alanine

Cited by 171 publications

References 11 publications

Distinction between intact and antibiotic‐inactivated bacteria by real‐time PCR after treatment with propidium monoazide

Distinction between intact and antibiotic‐inactivated bacteria by real‐time PCR after treatment with propidium monoazide

Bacteriolytic effect of teicoplanin

Structural and sequencing studies on peptides, proteins, and glycopeptide antibiotics by mass spectrometry

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