One-step synthesis of carbohydrate esters as antibacterial and antifungal agents

Alfindee, Madher N.; Zhang, Qian; Subedi, Yagya Prasad; Shrestha, Jaya P.; Kawasaki, Yukie; Grilley, Michelle; Takemoto, Jon Y.; Chang, Cheng‐Wei Tom

doi:10.1016/j.bmc.2017.12.038

Cited by 41 publications

(49 citation statements)

References 38 publications

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“…Finally, although some of the sugar-based esters here presented have already been published for other applications and also as possible antibacterial agents [22][23][24][29][30][31][32][33], a detailed comparative study concerning the properties of a relative large number of both aliphatic and aromatic amphiphilic carbohydrate esters as antimicrobial (Gram-positive, Gram-negative, and fungi) and mostly antibiofilm agents is still lacking.…”

Section: Scheme 3 Reagents and Conditions: (mentioning

confidence: 99%

“…Purification of the residue by flash chromatography (EtOAc/cyclohexane 8:2) gave 7a-e as white spongy solids and 8a-e as white crystal solids. (Scheme 2).6-O-Octanoyl-d-mannopyranose (mannose caprylate, URB1389) (7a)[29] Yield = 57%, α/β = 1:0.5. 1 H NMR (400 MHz, DMSO): δ = 0.86 (t, 3H+1.5H, J = 6.5 Hz, CH 3 ), 1.24-1.26 (m, 8H+4H), 1.50-1.53 (m, 2H+1H, OCCH 2 CH 2 ), 2.26-2.31 (m, 2H+1H, OCCH 2 CH 2 ), 3.21-3.33 (m, 1.5H, H 3β , H 4β , H 5β ), 3.35-3.41 (m, 1H, H 4α ), 3.49-3.55 (m, 2H+0.5H, H 2α , H 3α , H 2β ), 3.70 (ddd, 1H, J H5α-H6bα = 1.5 Hz, J H5α-H6aα = 7.0 Hz, J H5α-H4α = 9.0 Hz, H 5α ), 3.94-4.02 (m, 1H+0.5H, H 6aα , H 6aβ ), 4.27-4.32 (m, 1H+0.5H, H 6bα , H 6bβ ), 4.53-4.59 (m, 1H+1H, OH 2α , H 1β , OH 2β ), 4.63 (d, 1H, J OH3α-H3α = 4.0 Hz, OH 3α ), 4.66 (d, 0.5H, J OH3β-H3β = 5.5 Hz, OH 3β ), 4.86 (dd, 1H, J H1α-H2αJ H1α-OH1α = 4.5 Hz, H 1α ), 4.89 (d, 1H, J OH4α-H4α = 5.5 Hz, OH 4α ), 4.94 (d, 0.5H, J OH4β-H4β = 5.0 Hz, OH 4β ), 6.26 (d, 0.5H, J OH1β-H1β = 8.5 Hz, OH 1β ), 6.38 (d, 1H, J OH1α-H1α = 4.5 Hz, OH 1α ) ppm.…”

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confidence: 99%

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Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

et al. 2019

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A small library of sugar-based (i.e., glucose, mannose and lactose) monoesters containing hydrophobic aliphatic or aromatic tails were synthesized and tested. The antimicrobial activity of the compounds against a target panel of Gram-positive, Gram-negative and fungi was assessed. Based on this preliminary screening, the antibiofilm activity of the most promising molecules was evaluated at different development times of selected food-borne pathogens (E. coli, L. monocytogenes, S. aureus, S. enteritidis). The antibiofilm activity during biofilm formation resulted in the following: mannose C10 > lactose biphenylacetate > glucose C10 > lactose C10. Among them, mannose C10 and lactose biphenylacetate showed an inhibition for E. coli 97% and 92%, respectively. At MICs values, no toxicity was observed on Caco-2 cell line for all the examined compounds. Overall, based on these results, all the sugar-based monoesters showed an interesting profile as safe antimicrobial agents. In particular, mannose C10 and lactose biphenylacetate are the most promising as possible biocompatible and safe preservatives for pharmaceutical and food applications.

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Section: Scheme 3 Reagents and Conditions: (mentioning

confidence: 99%

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confidence: 99%

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

et al. 2019

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“…However, the anti‐microbial mechanisms of mono‐, di‐, oligosaccharide ester have not been investigated clearly. AlFindee et al reported that mannose myristate exerted its bioactivity via pore formation of the cell membrane of E. coli and S. aureus . The results reported by Zhoa et al also confirmed that sugar fatty acid esters can disrupt the cell membrane of bacteria based on observation under an electron microscope.…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, Hathcox and Beuchat observed that the growth of E. coli was unaffected in tryptic soy broth containing 1 mg mL −1 of a commercial sucrose laurate. AlFindee et al reported that among eight mannose esters with carbon chains from 2, 4, 6, 8, 10, 12, 14, and 16, the mannose ester with myristic acid (C‐14) (MANO14) was the most active compound with the lowest minimum inhibitory concentration (MIC) against S. aureus and E. coli and also showed broad ‐ spectrum activity against bacteria and fungi while having relatively low cytotoxicity toward animal cells. Ferrer et al and Zhao et al reported that disaccharide monoesters exhibited better anti‐microbial activity than monosaccharide monoesters.…”

Section: Introductionmentioning

confidence: 99%

Surface‐Active Properties and Anti‐Microbial Activities of Esterified Maltodextrins

et al. 2019

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The esterified maltodextrins (EMs) are prepared by enzymatic esterification of maltodextrin DE of 16 with three fatty acids (C‐10, C‐12, and C‐16). Three EMs are maltodextrin decanoate (DE16_D), maltodextrin laurate (DE16_L), and maltodextrin palmitate (DE16_P). Their surface‐active properties and anti‐microbial activities are investigated with various concentrations (0–20% (w/w)). All EMs exhibit surface activity that depends on the chain length of the fatty acid. The anti‐microbial activities of EMs and native maltodextrin are evaluated against Escherichia coli, a Gram‐negative bacterium, and Staphylococcus aureus a Gram‐positive bacterium. DE16_L is the most effective at retarding E. coli growth. The minimum inhibitory concentration (MIC) of DE16_L is 5% (w/w). Cell numbers of E. coli tend to decrease as the concentration increases for native maltodextrin, DE16_D, and DE16_L. On the other hand, DE16_P enhances the available cells of E. coli and S. aureus as concentration increases. EMs and native maltodextrin do not clearly retard the growth of S. aureus. This investigation indicates that the chain length of the fatty acid and the concentration of EMs affects their anti‐microbial ability.

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“…Phenyl acetylsalicylate which is an aromatic ester is used as an anti‐inflammatory drug. Also some esters are used as an antiseptic and antibacterial agent . Aromatic esters are also used in many steps of organic synthesis as a building block.…”

Section: Introductionmentioning

confidence: 99%

In Situ Carbonylative Synthesis of Aromatic Esters and Formation of Quinazoline‐2,4(1H,3H)‐diones by Chemical Fixation of CO₂ in Assistance of Polymer‐Supported Palladium Catalyst

et al. 2020

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In this work, a functionalized chloromethylated polystyrene supported polymer complex of palladium was designed and synthesized in the three‐step process. The synthesized heterogeneous Pd(DAP‐DEAS‐MERF) catalyst was characterized by Field emission scanning electron microscopy, Energy dispersive analysis of X‐rays, Elemental mapping, Atomic absorption spectroscopy, N2‐BET adsorption‐desorption isotherm, High‐resolution transmission electron microscopy, Thermogravimetric analysis‐Differential thermal analysis, Powder X‐Ray diffraction and Fourier‐transform infrared spectroscopy. The calculated surface area of the synthesized Pd(DAP‐DEAS‐MERF) catalyst is 4.018 m2/g and palladium content is found to be 5.16 % from AAS analysis. After this, the synthesized catalyst was successfully applied for the synthesis of aromatic esters and quinazoline‐2,4(1H,3H)‐diones in high efficiency. Aromatic esters were synthesized by the in‐situ carbonylative coupling reaction of iodobenzenes and phenols using chlorofirmand KOH as CO source.In the case of quinazoline‐2,4(1H,3H)‐diones synthesis, CO2 fixation reaction was performed with 2‐iodoaniline derivatives and tert‐butyl isocyanide/cyclohexyl isocyanide under atmospheric CO2 pressure. The synthesized products were identified by 1HNMR spectroscopy after purifying by coloum chromatography technique. In this report, Pd(DAP‐DEAS‐MERF) catalyst proved its efficiency by providing a comparatively better reaction condition than the other reported homogeneous and heterogeneous catalytic systems. Additionally, the catalyst isrecyclable up to six times and thermally stable up to 319 °C.

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One-step synthesis of carbohydrate esters as antibacterial and antifungal agents

Cited by 41 publications

References 38 publications

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

Surface‐Active Properties and Anti‐Microbial Activities of Esterified Maltodextrins

In Situ Carbonylative Synthesis of Aromatic Esters and Formation of Quinazoline‐2,4(1H,3H)‐diones by Chemical Fixation of CO₂ in Assistance of Polymer‐Supported Palladium Catalyst

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One-step synthesis of carbohydrate esters as antibacterial and antifungal agents

Cited by 41 publications

References 38 publications

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

Surface‐Active Properties and Anti‐Microbial Activities of Esterified Maltodextrins

In Situ Carbonylative Synthesis of Aromatic Esters and Formation of Quinazoline‐2,4(1H,3H)‐diones by Chemical Fixation of CO2 in Assistance of Polymer‐Supported Palladium Catalyst

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In Situ Carbonylative Synthesis of Aromatic Esters and Formation of Quinazoline‐2,4(1H,3H)‐diones by Chemical Fixation of CO₂ in Assistance of Polymer‐Supported Palladium Catalyst