Corrigendum to “γ-Alkylidene-γ-lactones and isobutylpyrrol-2(5H)-ones analogues to rubrolides as inhibitors of biofilm formation by Gram-positive and Gram-negative bacteria” [Bioorg. Med. Chem. Lett. 24 (2014) 1052–1056]

Pereira, Ulisses Alves; Barbosa, Luiz C. A.; Maltha, Célia R. A.; Demuner, Antônio J.; Masood, Mohammed A.; Pimenta, Aparecida Linhares

doi:10.1016/j.bmcl.2014.03.028

Cited by 4 publications

(9 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Various natural and synthetic furanones (1, 2a-g) and synthetic lactams (3, 4) (Figure 1) have been used successfully for inhibition of bacterial adherence. [10][11][12][13][14][15][16] However, a number of synthetic and natural compounds obtained from algae, fungi, and other organisms, although displaying inhibitory activity toward QS, have little or no therapeutic value due to their unstable nature or toxicity. Therefore, efforts have F I G U R E 1 Structure for (1) natural and (2a-g) synthetic furanones, (3,4) synthetic lactams, and (5) furan-2 (5H)-one been directed toward the development of safe and effective QS inhibitor compounds, both synthetic or from natural sources.…”

Section: Introductionmentioning

confidence: 99%

Functionalization of poly(lactic‐co‐glycolic acid) nanofibrous membranes with antibiofilm compounds

et al. 2021

Self Cite

View full text Add to dashboard Cite

The aim of this research was to investigate the activity of functionalized PLGA electrospun membranes in preventing Streptococcus mutans biofilm formation.PLGA nanofibres were functionalized with the additives Melaleuca alternifolia and Coffea canephora essential oils, furan-2(5H)-one, and a novel synthetic butyrolactam, in three concentrations (0.002%, 0.004%, and 0.008% w/v). Samples were characterized by SEM, FTIR-ATR, and GC-MS and exposed to S. mutans cultures. Planktonic growth was determined following a 24-and 48-h incubation period by spectrophotometry and the biofilm formation was evaluated by counting colony forming units. Cytotoxicity of the new biomaterials was assessed by MTS assay, through the quantification of viable placenta-derived stem cells grown over the functionalized nanofibrous membranes. Observation of the electrospun membranes on SEM images revealed the smooth and bead-free morphology of the nanofibres. No solvent residues were observed by FTIR-ATR, but the GC-MS results showed that N,N-dimethylformamide and dimethylsulfoxide were present as residues in the membranes after functionalization. Functionalization reduced bacterial attachment to membrane surfaces, with best results being obtained for M. alternifolia essential oil, furanone, and butyrolactam. Cytotoxicity results showed that furan-2(5H)-one-functionalized membranes demonstrated no statistically significant difference in the cell viability compared to the control membranes.

show abstract

Section: Introductionmentioning

confidence: 99%

Functionalization of poly(lactic‐co‐glycolic acid) nanofibrous membranes with antibiofilm compounds

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…35 e anteriormente empregadas com sucesso para o preparo de vários análogos de nostoclídeos [36][37][38][39] e rubrolídeos. [19][20][21][22][23][24] Para isso, as lactonas foram submetidas à reação com os aldeídos na presença de TBDMSOTf e DIPEA. Esse procedimento resulta na formação de um sililfurano intermediário que condensa com o aldeído resultando na formação de um sililéter intermediário.…”

Section: Sínteseunclassified

“…Nos últimos anos, nosso grupo tem relatado a síntese de vários butenolídeos análogos a compostos naturais e que apresentam atividades antibacteriana, 19,20 herbicida 21 , inibidora de fotossíntese [21][22][23] e citotóxica. 24 Dando continuidade a essa linha de pesquisa, e considerando que os cadiolídeos ainda foram pouco investigados em termos de atividade antimicrobiana, no presente artigo descrevemos a síntese de 21 novos análogos aos cadiolídeos empregando adaptações da metodologia desenvolvida por Boukouvalas e Thibault.…”

Section: Introductionunclassified

“…EM, m/z (%) 754 ([M +. ], C 27 H 18 Br 4 O 6 , 15), 755 ([M+1] + , 5), 756 ([M+2] + , 55), 757 ([M+3] + , 16), 758 ([M+4] + , 79), 759 ([M+5] + , 23), 760 ([M+6] + , 53), 761 ([M+7] + , 15), 762 ([M+8] + , 15), 679(9), 677 (9), 411 (13), 410(5), 409(24), 407(13), 295 (49), 294(10), 293 (100), 291 (52), 250(10), 248 (5), 239(16), 237(19), 235(10), 228 (59), 226(60), 215 (29), 213 (47), 211 (20), 200 (11), 199 (10), 198 (10), 119 (54), 103 (11), 89 (15), 77 (8), 76 (9), 75 (10), 63 (5), 57 (6). HRMS [ESI(+), IT-TOF]: calculado [C 27 H 19 Br 4 O 6 ] + 754,7910; encontrado 754,7905.…”

mentioning

confidence: 99%

“…EM, m/z (%) 634 ([M +. ], C 24 H 13 Br 3 O 6 , 3), 636 ([M+2] + , 9), 638 ([M+4] + , 9), 640 ([M+6] + , 3), 560(6), 558(13), 556(6), 214(5), 212(5), 122(8), 121 (100), 105(7), 93(19), 82(7), 80(6), 65(10).HRMS [ESI(+), IT-TOF]: calculado [C 24 H 13 Br 3 O 6 ] + 634,8335; encontrado 634,8340. (Z)-4-(3-bromo-4-hidroxifenil)-5-(3,5-dibromo-4-hidroxibenzilideno)-3-(4-metoxibenzoil)furan-2(5H)-ona (16h')O composto 16h' foi obtido como um sólido laranja, em 25% de rendimento, após purificação por cromatografia em coluna de sílica gel.…”

unclassified

See 2 more Smart Citations

Inibição Do Crescimento De Microrganismos Patogênicos Induzida Por Butenolídeos Análogos Aos Cadiolídeos

Mairink

Barbosa

Maltha

et al. 2019

View full text Add to dashboard Cite

INHIBITORY EFFECT ON GROWTH OF PATHOGENIC MICROORGANISMS INDUCED BY BUTENOLIDES RELATED TO CADIOLIDES. The increasing number of antibiotic resistant microorganisms requires the development of new drugs. In this context, natural cadiolides are promising leads as they present potent antimicrobial activity and low cytotoxicity. In this work we report the synthesis of 21 new cadiolide analogues. The synthesis involved a Diels−Alder cycloaddition/ cycloreversion reaction between an oxazole and different ynones, affording four intermediate butenolides (14a-d) in 61-81% yield. These intermediates were subjected to a vinylogous Knoevenagel condensation, followed by demethylation of the methoxylated compounds, affording all 21 analogues in good yields. The antibiotic activity of all compounds was evaluated against a panel of five microorganisms. The bioassays on the microbial growth showed that the cadiolides are more active for Gram-positive than Gram-negative bacteria, and have low activity against the fungus C. albicans. The most active compounds (14b, 15b, 15c and 16e) were effective against S. aureus showing IC 50 in the range of 1.8-6.0 µg mL-1. The results also indicated that the nature and position of substituent groups on the aromatic moieties have some effect on the activities.

show abstract

Rubrolide analogues and their derived lactams as potential anticancer agents

et al. 2016

View full text Add to dashboard Cite

show abstract

Corrigendum to “γ-Alkylidene-γ-lactones and isobutylpyrrol-2(5H)-ones analogues to rubrolides as inhibitors of biofilm formation by Gram-positive and Gram-negative bacteria” [Bioorg. Med. Chem. Lett. 24 (2014) 1052–1056]

Cited by 4 publications

References 0 publications

Functionalization of poly(lactic‐co‐glycolic acid) nanofibrous membranes with antibiofilm compounds

Functionalization of poly(lactic‐co‐glycolic acid) nanofibrous membranes with antibiofilm compounds

Inibição Do Crescimento De Microrganismos Patogênicos Induzida Por Butenolídeos Análogos Aos Cadiolídeos

Rubrolide analogues and their derived lactams as potential anticancer agents

Contact Info

Product

Resources

About