Esters and amides of Edeine A.

Mazerski, Jan; Wojciechowska, H.; Zgoda, Włodzimierz; Woynarowska, Barbara; Borowski, Edward

doi:10.7164/antibiotics.34.28

Cited by 7 publications

(2 citation statements)

References 12 publications

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“…Edeines are pentapeptides with a unique backbone, composed of a glycine, four nonproteinogenic amino acids and a C‐terminal polyamine (spermidine in edeine A 1 and guanyl‐spermidine in edeine B 1 ) (Fig. 1) (Mazerski et al ., 1981; Czerwinski et al ., 1983; Gumieniak et al ., 1983). The biosynthesis of natural products has advantages over chemical synthesis in laboratories due to its low cost and high intensity (Kunga Sugumaran et al ., 2016).…”

Section: Introductionmentioning

confidence: 99%

Enhancement of edeine production in Brevibacillus brevis X23 via in situ promoter engineering

Liu

Zhang

Wang

et al. 2021

Microbial Biotechnology

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Edeines, a group of cationic antimicrobial peptides produced by the soil bacterium Brevibacillus, have broad biological effects, such as antimicrobial, anticancer and immunosuppressive activities. However, the yield of edeines in wild-type (WT) Brevibacillus is extremely low, and chemical synthesis of edeines is a time-consuming process. Genetic engineering has proven to be an effective approach to produce antibiotics with high yield. In this study, the edeine biosynthetic gene cluster (ede BGC), which is involved in edeine production, was identified and characterized in Brevibacillus brevis X23. To improve edeine production in B. brevis X23, the ede BGC promoter was replaced with six different promoters, P mwp , P spc , P xylA , P shuttle-09 , P grac or P 43 , through double-crossover homologous recombination. The new promoters significantly increased the expression of the ede BGC as well as edeine production by 2.9 AE 0.4 to 20.5 AE 1.2-fold and 3.6 AE 0.1to 8.7 AE 0.7fold respectively. The highest yield of edeines (83.6 mg l À1 ) was obtained in B. brevis X23 with the P mwp promoter. This study provides a practical approach for producing high yields of edeines in B. brevis.

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Section: Introductionmentioning

confidence: 99%

Enhancement of edeine production in Brevibacillus brevis X23 via in situ promoter engineering

Liu

Zhang

Wang

et al. 2021

Microbial Biotechnology

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“…Taking into consideration the unique biological properties of these peptides (the immunological activity and the capacity for universal inhibition of protein biosynthesis) and the difficulties in the chemical synthesis of natural antibiotics, we undertook the synthesis of edeine analogues with simplified structures. It was previously demonstrated that the presence of the free ionizable carboxyl group in the (2R,6S,7R)-A 2 ha moiety was not essential for the biological activity of edeines [20,21]. As a continuation of our research project [22], we recently synthesized the following edeine antibiotic analogues ( Compounds 1-4 were shown to exhibit significantly diminished antibacterial and antifungal activities [22], and they did not display toxic effects towards mammalian cells [23].…”

Section: Introductionmentioning

confidence: 99%

The immunoregulatory effects of edeine analogues in mice

Czajgucki¹,

Zimecki²,

Andruszkiewicz³

2007

Cellular and Molecular Biology Letters

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Abstract:The edeines analogs were tested in several in vitro and in vivo assays using the mouse model, with edeine B (peptide W1) and cyclosporine A as reference compounds. The peptides displayed moderate, stimulatory effects on concanavalin A-induced (ConA-induced) splenocyte proliferation, whereas their effects on pokeweed mitogen-induced (PWM-induced) splenocyte proliferation were inhibitory. The peptides inhibited lipopolysacharide-induced (LPSinduced) tumor necrosis factor alpha production but had little effect on interleukin 6 production. In the model of the humoral immune response in vitro to sheep red blood cells, peptide 1 was distinctly stimulatory in the investigated concentrations (1-100 μg/ml), whereas peptides 3 and 4 only stimulated the number of antibody-forming cells at the highest concentration (100 μg/ml). In the model of the delayed type hypersensitivity in vivo to ovalbumin, the peptides were moderately suppressive (3 being the most active). The reference peptide W1 stimulated ConA-induced cell proliferation at 1-10 μg/ml but was inhibitory at 100 μg/ml. It also inhibited PWM-induced cell proliferation in a dosedependent manner. This peptide had no effect on the humoral immune response in vitro or on cytokine production, but inhibited DTH reaction in vivo. The relationship between structure and activity, and a possible mode of action of the peptides, is discussed in this paper.

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Structure activity relationship studies on the antimicrobial activity of novel edeine A and D analogues

2006

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Edeines are pentapeptide amide antibiotics composed of four nonprotein amino acids, glycine, and polyamine. They exhibit antimicrobial and immunosuppressive activities and are universal inhibitors of translation. Moreover, it was proven that the free ionizable carboxy group in the (2R, 6S, 7R)-2,6-diamino-7-hydroxyazelaic acid moiety is not essential for biological activity of these compounds. In this paper we describe the synthesis of four novel edeine A and D analogues in which the above-mentioned acid residue was replaced with the (3R, 4S)- or (3S, 4S)-4,5-diamino-3-hydroxypentanoic acid moiety. In one compound we also introduced into molecule the 3-N,N-dimethyl derivative of (S)-2,3-diaminopropanoic acid to prevent the transpeptidation process, which results in the loss of biological activity of alpha-isomers of edeines. All peptides were synthesized applying the active ester and azide methods and on the basis of the coupling of suitable N-terminal tripeptides with proper C-terminal dipeptide amides. The activities of the newly obtained edeine analogues against selected strains of bacteria and fungi are also presented.

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Esters and amides of Edeine A.

Abstract: Methods for the synthesis of esters and amides of edeine A were developed and a number of derivatives of this type was obtained and characterized. The antimicrobial activities of the derivatives are comparable to the activity of the native antibiotic and indicate that the

Cited by 7 publications

References 12 publications

Enhancement of edeine production in Brevibacillus brevis X23 via in situ promoter engineering

Enhancement of edeine production in Brevibacillus brevis X23 via in situ promoter engineering

The immunoregulatory effects of edeine analogues in mice

Structure activity relationship studies on the antimicrobial activity of novel edeine A and D analogues

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