Synthesis, Pass Predication of Antimicrobial Activity and Pharmacokinetic Properties of Hexanoyl Galactopyranosides and Experimental Evaluation of their Action against Four Human Pathogenic Bacteria and Four Fungal Strains

Matin, Mohammed Mahbubul; Bhuiyan, M. M. H.; Kibria, Sayed M.; Hasan, Md. Saif

doi:10.1007/s11094-022-02687-y

Cited by 3 publications

(6 citation statements)

References 33 publications

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“…The results are listed as Pa (probability for an active compound) and Pi (probability for an inactive compound). In the present study, Pa and Pi for different stearates (4)(5)(6)(7)(8)(9)(10)(11) are summarized in Table 2. Its FT-IR spectrum (Figure S28) had no OH stretching bands, indicating hexanoylation of the molecule.…”

Section: Prediction Of Activity Spectra For Substances (Pass) Of 3-11mentioning

confidence: 99%

“…The results are listed as Pa (probability for an active compound) and Pi (probability for an inactive compound). In the present study, Pa and Pi for different stearates (4)(5)(6)(7)(8)(9)(10)(11) are summarized in Table 2. PASS biological analysis (Table 2) indicates 0.57 < Pa < 0.62 for antibacterial and 0.68 < Pa < 0.73 for antifungal, suggesting that the rhamnose stearates 4-11 should be more active against fungal organisms than bacterial pathogens.…”

Section: Prediction Of Activity Spectra For Substances (Pass) Of 3-11mentioning

confidence: 99%

“…Sample Availability: Samples of the compounds (4)(5)(6)(7)(8)(9)(10)(11) are available on request from the authors.…”

Section: Acknowledgmentsmentioning

confidence: 99%

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Rhamnopyranoside-Based Fatty Acid Esters as Antimicrobials: Synthesis, Spectral Characterization, PASS, Antimicrobial, and Molecular Docking Studies

et al. 2023

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The most widely used and accessible monosaccharides have a number of stereogenic centers that have been hydroxylated and are challenging to chemically separate. As a result, the task of regioselective derivatization of such structures is particularly difficult. Considering this fact and to get novel rhamnopyranoside-based esters, DMAP-catalyzed di-O-stearoylation of methyl α-l-rhamnopyranoside (3) produced a mixture of 2,3-di-O- (4) and 3,4-di-O-stearates (5) (ratio 2:3) indicating the reactivity of the hydroxylated stereogenic centers of rhamnopyranoside as 3-OH > 4-OH > 2-OH. To get novel biologically active rhamnose esters, di-O-stearates 4 and 5 were converted into six 4-O- and 2-O-esters 6–11, which were fully characterized by FT-IR, 1H, and 13C NMR spectral techniques. In vitro antimicrobial assays revealed that fully esterified rhamnopyranosides 6–11 with maximum lipophilic character showed better antifungal susceptibility than antibacterial activity. These experimental findings are similar to the results found from PASS analysis data. Furthermore, the pentanoyl derivative of 2,3-di-O-stearate (compound 6) showed better antifungal functionality against F. equiseti and A. flavus, which were found to be better than standard antibiotics. To validate the better antifungal results, molecular docking of the rhamnose esters 4–11 was performed with lanosterol 14α-demethylase (PDB ID: 3LD6), including the standard antifungal antibiotics ketoconazole and fluconazole. In this instance, the binding affinities of 10 (−7.6 kcal/mol), 9 (−7.5 kcal/mol), and 7 (−6.9 kcal/mol) were better and comparable to fluconazole (−7.3 kcal/mol), indicating the likelihood of their use as non-azole type antifungal drugs in the future.

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Section: Prediction Of Activity Spectra For Substances (Pass) Of 3-11mentioning

confidence: 99%

“…The results are listed as Pa (probability for an active compound) and Pi (probability for an inactive compound). In the present study, Pa and Pi for different stearates (4)(5)(6)(7)(8)(9)(10)(11) are summarized in Table 2. PASS biological analysis (Table 2) indicates 0.57 < Pa < 0.62 for antibacterial and 0.68 < Pa < 0.73 for antifungal, suggesting that the rhamnose stearates 4-11 should be more active against fungal organisms than bacterial pathogens.…”

Section: Prediction Of Activity Spectra For Substances (Pass) Of 3-11mentioning

confidence: 99%

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Rhamnopyranoside-Based Fatty Acid Esters as Antimicrobials: Synthesis, Spectral Characterization, PASS, Antimicrobial, and Molecular Docking Studies

et al. 2023

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“…Several protective measures have been reported for the control of COVID-19 situation along with the administration of antiviral drugs [58]. It was observed that several SEs showed antifungal properties [59,60] and antifungal agents were reported to have antiviral efficacy, especially they were checked for anti SARS-CoV-19 tests in vitro [61]. Encouraged by these results, four galactopyranose esters 5-8 were selected for molecular docking with main proteases (7BQY and 6LU7).…”

Section: Molecular Docking: Binding Affinity With Sars-cov-2 Main Pro...mentioning

confidence: 99%

In Silico Testing of Some Protected Galactopyranose as SARS-CoV-2 Main Protease Inhibitors

Azad

Islam

Chowdhury

et al. 2022

J. Appl. Sci. Process Eng.

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An outbreak of novel Coronavirus disease (COVID-19 or 2019-nCoV) due to the severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) has already demonstrated a fatal death toll all over the world. To cure this viral infection, a number of compounds of different categories have been investigated in silico. Some of the compounds showed better binding energy with COVID-19-related proteins. However, until now there is no appropriate drug except a vaccine. It was found that many antifungal drugs are used for COVID-19 patients in hospitals. Many monosaccharide esters have been reported to have antifungal potential. Thus, in the present study, some protected galactopyranose esters are chosen for molecular docking with SARS-CoV-2 main proteases (PDB id: 7BQY and 6LU7). A docking study revealed that galactopyranose esters 5-8 have very good docking scores (-8.4 to -6.5 kcal/mol) compared to the standard drugs azithromycin, remdesivir, and hydroxychloroquine. To explain such good scores interaction between amino acid residues of proteins and compounds in their docked complexes are calculated and duly discussed in this study.

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“…As a continuation of our research work on bioactive molecules [37][38][39][40][41], we were interested to check their anticancer potentiality. Thus, four natural rhamnopyranoside esters are considered for their anticancer properties via molecular docking and ADMET (absorption, distribution, metabolism, excretion, and toxicity) studies.…”

Section: Introductionmentioning

confidence: 99%

Naturally Occurring Rhamnopyranosides as Anticancer Agents: Molecular Docking and ADMET Study

Islam

Sultan²,

Hossain³

et al. 2022

J. Appl. Sci. Process Eng.

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After heart disease, cancer continues to be the second most prevalent cause of death in the USA. Several chemotherapeutic treatments (drugs) are available for cancer that use powerful chemicals to kill the body's rapidly proliferating cells. However, recent research disclosed that many clinically viable anticancer drugs have been developed with the help of chemicals originating from plants. A number of phytochemicals isolated from plants possess rhamnopyranoses and some of them are acyl rhamnopyranoses. Encouragingly, such compounds were reported for their cell proliferation and migration inhibition activities against invasive human triple-negative breast cancer cells. In this study, four naturally occurring rhamnopyranose esters were checked against three cancer-related proteins (PDB IDs: 3TJM, 4OAR, and 5FGK) via molecular docking. Rhamnose compounds 3-6 showed better binding energy compared to the related standard drugs in use in the hospitals. Compound 6 was found highly potential against all the proteins (-8.5 to -11.3 kcal/mol). ADMET studies have also been discussed in this respect. This study indicated that natural rhamnopyranose esters could be used to stop the spreading of cancer cells like other reported sugar fatty acid esters (SFAEs).

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Synthesis, Pass Predication of Antimicrobial Activity and Pharmacokinetic Properties of Hexanoyl Galactopyranosides and Experimental Evaluation of their Action against Four Human Pathogenic Bacteria and Four Fungal Strains

Cited by 3 publications

References 33 publications

Rhamnopyranoside-Based Fatty Acid Esters as Antimicrobials: Synthesis, Spectral Characterization, PASS, Antimicrobial, and Molecular Docking Studies

Rhamnopyranoside-Based Fatty Acid Esters as Antimicrobials: Synthesis, Spectral Characterization, PASS, Antimicrobial, and Molecular Docking Studies

In Silico Testing of Some Protected Galactopyranose as SARS-CoV-2 Main Protease Inhibitors

Naturally Occurring Rhamnopyranosides as Anticancer Agents: Molecular Docking and ADMET Study

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