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Furlan, Renata Ligia de Araujo; Garrido, Leandro M.; Brumatti, Gabriela; Amarante-Mendes, Gustavo P.; Martins, R. A.; Facciotti, Maria Cândida Reginato; Padilla, Gabriel

doi:10.1023/a:1020633909762

Cited by 21 publications

(4 citation statements)

References 24 publications

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“…We hypothesize that this discrepancy results from intercalation as intercalation is known to reduce electrophoretic mobility. 77,78 A comparison with DNR (5) indicated that hybrid 7 is marginally less effective at inhibiting the relaxation of −SC DNA (Figure 3a vs Figure 3b) and that both compounds inhibit +SC with largely the same effectiveness (Figure 3c vs Figure 3d).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis and Cytotoxic Evaluation of Arimetamycin A and Its Daunorubicin and Doxorubicin Hybrids

et al. 2021

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The arimetamycin A glycan governs the compound’s cytotoxicity (IC 50 ). To study this branched, deoxy-amino disaccharide, we designed and synthesized a modified acyl donor that underwent glycosylation with three anthracycline aglycones: steffimycinone, daunorubicinone, and doxorubicinone. The result of the approach was a synthesis of arimetamycin A and two novel hybrid anthracyclines. Each molecule exhibited enhanced cytotoxicity in comparison to the parent anthracyclines, steffimycin B, daunorubicin, and doxorubicin. An orienting mechanistic evaluation revealed that the daunorubicin hybrid inhibits the ability of human topoisomerase IIα to relax negatively and positively supercoiled DNA.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis and Cytotoxic Evaluation of Arimetamycin A and Its Daunorubicin and Doxorubicin Hybrids

et al. 2021

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“…For the gel-based assay, the intercalation ability of hLig1 inhibitor with DNA substrate was evaluated as discussed earlier. 26 In brief, linearized pUC18 plasmid was incubated with hLig1 inhibitor up to 600 μM concentration for 30 min at 37 °C. Doxorubicin and ampicillin were used as positive and negative controls, respectively.…”

Section: Ethylmentioning

confidence: 99%

Design, synthesis and anticancer activity of dihydropyrimidinone–semicarbazone hybrids as potential human DNA ligase 1 inhibitors

et al. 2016

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“…Masarimycin was investigated for its ability to inhibit nuclease activity and intercalate DNA in established assays (Fig. S7) [20, 21]. Masarimycin showed no inhibition of nuclease activity or ability to intercalate DNA, suggesting the antagonism observed is likely not due to direct interaction with DNA or nucleases.…”

Section: Resultsmentioning

confidence: 99%

“…To determine if masarimycin intercalates DNA, DNA mobility shift assays were performed as previously described using BamHI-linearized pUC18 plasmid [20]. The known DNA intercalator actinomycin D was used as a control.…”

Section: Methodsmentioning

confidence: 99%

Inhibition of Streptococcus pneumoniae growth by masarimycin

et al. 2022

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Despite renewed interest, development of chemical biology methods to study peptidoglycan metabolism has lagged in comparison to the glycobiology field in general. To address this, a panel of diamides were screened against the Gram-positive bacterium Streptococcus pneumoniae to identify inhibitors of bacterial growth. The screen identified the diamide masarimycin as a bacteriostatic inhibitor of S. pneumoniae growth with an MIC of 8 µM. The diamide inhibited detergent-induced autolysis in a concentration-dependent manner, indicating perturbation of peptidoglycan degradation as the mode-of-action. Cell based screening of masarimycin against a panel of autolysin mutants, identified a higher MIC against a ΔlytB strain lacking an endo-N-acetylglucosaminidase involved in cell division. Subsequent biochemical and phenotypic analyses suggested that the higher MIC was due to an indirect interaction with LytB. Further analysis of changes to the cell surface in masarimycin treated cells identified the overexpression of several moonlighting proteins, including elongation factor Tu which is implicated in regulating cell shape. Checkerboard assays using masarimycin in concert with additional antibiotics identified an antagonistic relationship with the cell wall targeting antibiotic fosfomycin, which further supports a cell wall mode-of-action.

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Cited by 21 publications

References 24 publications

Synthesis and Cytotoxic Evaluation of Arimetamycin A and Its Daunorubicin and Doxorubicin Hybrids

Synthesis and Cytotoxic Evaluation of Arimetamycin A and Its Daunorubicin and Doxorubicin Hybrids

Design, synthesis and anticancer activity of dihydropyrimidinone–semicarbazone hybrids as potential human DNA ligase 1 inhibitors

Inhibition of Streptococcus pneumoniae growth by masarimycin

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