.BETA.-Lactam antibiotics. I. Comparative structure-activity relationships of 6-acylaminopenicillanic acid derivatives and their 6-(D-.ALPHA.-acylaminophenylacetamido) penicillanic acid analogues.

Ferres, H.; Basker, Michael J.; O’Hanlon, Peter J.

doi:10.7164/antibiotics.27.922

Cited by 11 publications

(2 citation statements)

References 15 publications

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“…Our data are consistent with previous findings that amino group modifications of aminopenicillins enhanced antipseudomonal activity. 14,16,18,[32][33][34][35] A noteworthy finding is that among the derivatives synthesized in this study, DTPA-Amox had potent antipseudomonal activity against clinical isolates of P. aeruginosa that were resistant to piperacillin and carbenicillin (Figure 5; Table 1).…”

Section: Discussionmentioning

confidence: 63%

Development of potent antipseudomonal β‐lactams by means of polycarboxylation of aminopenicillins

Akter

Migiyama

Tsutsuki

et al. 2021

Microbiology and Immunology

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Pseudomonas aeruginosa is a Gram-negative opportunistic pathogen that presents a serious risk to immunosuppressed individuals and other extremely vulnerable patients such as those in intensive care units. The emergence of multidrug-resistant Pseudomonas strains has increased the need for new antipseudomonal agents. In this study, a series of amino groupmodified aminopenicillin derivatives was synthesized that have different numbers of carboxyl groups and structurally resemble carboxypenicillin-ureidopenicillin hybrids, and their antipseudomonal activities were evaluated. Among the derivatives synthesized, diethylenetriaminepentaacetic acid (DTPA)-modified amoxicillin (DTPA-Amox) showed potent antipseudomonal activity, not only against the laboratory strain PAO1 but also against clinically isolated Pseudomonas strains that were resistant to piperacillin and carbenicillin. DTPA-Amox had no obvious cytotoxic effects on cultured mammalian cells. In addition, in an in vivo model of leukopenia, DTPA-Amox treatment produced a moderate but statistically significant improvement in the survival of mice with P. aeruginosa strain PAO1 infection. These data suggest that polycarboxylation by DTPA conjugation is an effective approach to enhance antipseudomonal activity of aminopenicillins.

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Section: Discussionmentioning

confidence: 63%

Development of potent antipseudomonal β‐lactams by means of polycarboxylation of aminopenicillins

Akter

Migiyama

Tsutsuki

et al. 2021

Microbiology and Immunology

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show abstract

“…It has been reported elsewhere that acylation or other N substitution of the amino group in the side chain of a penicillin such as ampicillin has resulted in some penicillins that have improved antipseudomonal activity: sulfoaminobenzylpenicillin, BL-P 1462, guanylureido, and other acylureidobenzylpenicillins, BL-P 1654, BL-P 1597, BAY e6905, and others (4,7,15,16).…”

mentioning

confidence: 99%

PC-904, a Novel Broad-Spectrum Semisynthetic Penicillin with Marked Antipseudomonal Activity: Microbiological Evaluation

1976

Antimicrob Agents Chemother

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Natural Occurrence and Industrial Applications of d‐Amino Acids: An Overview

Martínez‐Rodríguez

Martínez-Gómez

Rodríguez‐Vico

et al. 2010

Chemistry & Biodiversity

114

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Interest in D-amino acids has increased in recent decades with the development of new analytical methods highlighting their presence in all kingdoms of life. Their involvement in physiological functions, and the presence of metabolic routes for their synthesis and degradation have been shown. Furthermore, D-amino acids are gaining considerable importance in the pharmaceutical industry. The immense amount of information scattered throughout the literature makes it difficult to achieve a general overview of their applications. This review summarizes the state-of-the-art on D-amino acid applications and occurrence, providing both established and neophyte researchers with a comprehensive introduction to this topic.

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.BETA.-Lactam antibiotics. I. Comparative structure-activity relationships of 6-acylaminopenicillanic acid derivatives and their 6-(D-.ALPHA.-acylaminophenylacetamido) penicillanic acid analogues.

Cited by 11 publications

References 15 publications

Development of potent antipseudomonal β‐lactams by means of polycarboxylation of aminopenicillins

Development of potent antipseudomonal β‐lactams by means of polycarboxylation of aminopenicillins

PC-904, a Novel Broad-Spectrum Semisynthetic Penicillin with Marked Antipseudomonal Activity: Microbiological Evaluation

Natural Occurrence and Industrial Applications of d‐Amino Acids: An Overview

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