Evaluation of Octyl-β-D-Glucopyranoside (OGP) for Cytotoxic, Hemolytic, Thrombolytic, and Antibacterial Activity

Dinesh, Murugesan; Deepika, Subramanyam; Harishkumar, Rajendran; Selvaraj, Chinnadurai Immanuel; Roopan, Selvaraj Mohana

doi:10.1007/s12010-017-2661-7

Cited by 9 publications

(6 citation statements)

References 21 publications

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“…They found that caprinoylfructose had the greatest antimicrobial activity against the four organisms that they examined . There is some evidence that Gram-positive bacteria are more susceptible to antibiotic surfactants than are the Gram-negative bacteria. , We examined the antibiotic effectiveness of the C -glycoside surfactants against four organisms with importance in human, animal, and crop plant health and across the range of Gram stain responsiveness. Bacillus subtilis is a model Gram-positive microorganism.…”

Section: Resultsmentioning

confidence: 99%

New Family of Surfactants from Biobased Materials

Jackson

Evans

Price

et al. 2021

ACS Sustainable Chem. Eng.

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β-C-Glycoside ketone derivatives of glucose, lactose, and maltose were converted to amines via a reductive amination using 5 wt % Rh/Al 2 O 3 in ammoniacal methanol under 34 bar H 2 . The amines were isolated and then were used as the amine in the reductive amination of 2-undecanone that can be prepared from the seed oil of Cuphea. The resulting β-C-glycoside-2-aminoundecanes were characterized by MALDI-TOF mass spectrometry and 2D NMR. The critical micelle concentrations of the products as measured by isothermal calorimetry titration ranged from 1 to 5 mM, and the micelles carry a positive charge as measured by zeta potentials. The β-C-glycoside 2-aminoundecanes have antimicrobial activity against Bacillus subtilis, Pseudomonas aeruginosa, Erwinia amylovora, and Escherichia coli, with the C-glucoside derivative having the greatest activity with a minimum inhibitory concentration of 0.31 mM and a minimum bactericide concentration of 0.62 mM against the Gram positive organisms. Against the Gram negative Erwinia and Escherichia, the MIC is 0.62 mM. This work introduces a new family of sustainable surfactants with potential uses in personal care and cleaning products.

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Section: Resultsmentioning

confidence: 99%

New Family of Surfactants from Biobased Materials

Jackson

Evans

Price

et al. 2021

ACS Sustainable Chem. Eng.

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“…It is also useful for solubilizing enzymes, receptors, and phosphatidylcholine. It is nontoxic in cell lines, and inhibited the starch hydrolyzing enzyme α-amylase to a good extent [45]. Furthermore, it was observed that the dimolar acylation of 4 in only pyridine solution gave 3,6-di-Opentanoate in lower yield (56%) [3].…”

Section: Synthesis Of 36-di-o-pentanoatementioning

confidence: 99%

Efficient Synthetic Technique, PASS Predication, and ADMET Studies of Acylated n-Octyl Glucopyranosides

Ali

Karim

Matin

2021

JASPE

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Direct dimolar pentanoylation of octyl β-D-glucopyranoside (OBG) in pyridine-chloroform solvent system furnished the corresponding 3,6-di-O-pentanoate in improved yield. The pentanoate was further converted into three 2,4-di-O-acyl esters to get novel octyl glucopyranosides. To explore medicinal probability of OBG-based esters all the synthesized compounds were subjected for in silico PASS (prediction of activity spectra for substances) predication and ADMET (absorption, distribution, metabolism, excretion, and toxicity) studies. Both the studies indicated that OBG derived carbohydrate fatty acid (CFA) esters are potential alternative for multidrug resistant (MDR) pathogens, especially for fungal infections.

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“…Therefore, new and more efficient anticancer agents are required to battle different cancer diseases. Furthermore, according to the various clinical studies [40,41], it has been shown that compounds having the ability to block or suppress the proliferation of cancer cell by the induction of apoptotic cell death are considered as strong anticancer agents.…”

Section: Cytotoxic Activitymentioning

confidence: 99%

Biological Activities Evaluation of Enantiopure Isoxazolidine Derivatives: In Vitro, In Vivo and In Silico Studies

Mosbah

Chahdoura

Mannai

et al. 2018

Appl Biochem Biotechnol

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A series of enantiopure isoxazolidines (3a-c) were synthesized by 1,3-dipolar cycloaddition between a (-)-menthone-derived nitrone and various terminal alkenes. The screened compounds were evaluated for their antioxidant activity by two in vitro antioxidant assays, including β-carotene/linoleic acid bleaching, and inhibition of lipid peroxidation (thiobarbituric acid reactive species, TBARS). The results revealed that compound 3b (EC = 0.55 ± 0.09 mM) was the most potent antioxidant as compared to the standard drug (EC = 2.73 ± 0.07 mM) using the TBARS assay. Furthermore, the antimicrobial activity was assessed using disc diffusion and microdilution methods. Among the synthesized compounds, 3c was found to be the most potent antimicrobial agent as compared to the standard drug. Subsequently, the acute toxicity study has also been carried out for the newly synthesized compounds and the experimental studies revealed that all compounds were safe up to 500 mg/kg and no death of animals were recorded. The cytotoxicity of these compounds was assessed by the MTT cell proliferation assay against the continuous human cell lines HeLa and compound 3c (GI = 46.2 ± 1.2 μM) appeared to be more active than compound 3a (GI = 200 ± 2.8 μM) and 3b (GI = 1400 ± 7.8 μM). Interestingly, all tested compounds displayed a good α-amylase inhibitory activity in competitive manner with IC values ranging between 23.7 and 64.35 μM when compared to the standard drug acarbose (IC = 282.12 μM). In addition, molecular docking studies were performed to understand the possible binding and the interaction of the most active compounds to the α-amylase pocket.

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Evaluation of Octyl-β-D-Glucopyranoside (OGP) for Cytotoxic, Hemolytic, Thrombolytic, and Antibacterial Activity

Cited by 9 publications

References 21 publications

New Family of Surfactants from Biobased Materials

New Family of Surfactants from Biobased Materials

Efficient Synthetic Technique, PASS Predication, and ADMET Studies of Acylated n-Octyl Glucopyranosides

Biological Activities Evaluation of Enantiopure Isoxazolidine Derivatives: In Vitro, In Vivo and In Silico Studies

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