Physico-chemical characterization and pharmacological evaluation of sulfated polysaccharides from three species of Mediterranean brown algae of the genus Cystoseira

Ammar, Hiba Hadj; Lajili, Sirine; Said, Rafik Ben; Cerf, Didier Le; Bouraoui, Abderrahman; Majdoub, Hatem

doi:10.1186/s40199-015-0089-6

Cited by 75 publications

(43 citation statements)

References 29 publications

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“…The divination may be supposed valid for only those compounds which fall into this domain [15]. Therefore standardized residuals of the activity were calculated and plotted against leverage values (h).…”

Section: Resultsmentioning

confidence: 99%

Prediction of new Hsp90 inhibitors based on 3,4-isoxazolediamide scaffold using QSAR study, molecular docking and molecular dynamic simulation

2017

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BackgroundHeat shock protein90 (Hsp90) are overexpressed in tumor cells, so the inhibition of the Hsp90 ATPase activity would be a significantly effective strategy in cancer therapy.MethodsIn the current study, 3,4-isoxazolediamide derivatives were suggested as an Hsp90 inhibitor for anti-cancer therapy. Multiple linear regression (MLR) and genetic algorithm of partial least square (GA-PLS) methods were performed to build models to predict the inhibitory activity of Hsp90. The leave-one out (LOO) cross-validation and Y-randomization tests were performed to models’ validation. The new ligands were monitored by applicability domain. Molecular docking studies were also conducted to evaluate the mode of interaction of these compounds with Hsp90. Identification of the likely pathways into the active site pocket and the involved residues were performed by CAVAER 3.0.1 software. According to QSAR models and docking analysis, three new compounds were predicted. 50 ns molecular dynamic simulation was performed for the strongest synthesized compound and the best predicted compound in terms of binding energy and interactions between ligand and protein.ResultsThe made models showed the significance of size, shape, symmetry, and branching of molecules in inhibitory activities of Hsp90. Docking studies indicated that two hydroxyl groups in the resorcinol ring were important in interacting with Asp93 and the orientation of these groups was related to substitution of different R1 groups. Comparing of molecular dynamic simulation (MDs) results shows that new compound perched in active site with lower binding energy than the best synthesized compound.ConclusionThe QSAR and docking analyses shown to be beneficial tools in the proposal of anti-cancer activities and a leader to the synthesis of new Hsp90 inhibitors based 3,4-isoxazolediamide. The MDs confirmed that predicted ligand is steady in the Hsp90 active sites.Graphical Abstract

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Section: Resultsmentioning

confidence: 99%

Prediction of new Hsp90 inhibitors based on 3,4-isoxazolediamide scaffold using QSAR study, molecular docking and molecular dynamic simulation

2017

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“…Due to several complicated pre-treatment steps, general protocols always employ a single incubation step using the ternary mixture composed of CH 3 OH:CH 3 Cl: [103], binary mixture of CH 2 Cl 2 :EtOH (94.2:5.8, v/v) [104], or aqueous ethanol (e.g., 95% v/v) [105,106] to remove pigments [107], polyphenols [51,103] and lipids [108]. Nevertheless, pre-treatment steps may be insufficient for complete removal or prevention of some residual co-extraction.…”

Section: Figurementioning

confidence: 99%

Fucoidans: Downstream Processes and Recent Applications

Zayed

Ulber

2020

Marine Drugs

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Fucoidans are multifunctional marine macromolecules that are subjected to numerous and various downstream processes during their production. These processes were considered the most important abiotic factors affecting fucoidan chemical skeletons, quality, physicochemical properties, biological properties and industrial applications. Since a universal protocol for fucoidans production has not been established yet, all the currently used processes were presented and justified. The current article complements our previous articles in the fucoidans field, provides an updated overview regarding the different downstream processes, including pre-treatment, extraction, purification and enzymatic modification processes, and shows the recent non-traditional applications of fucoidans in relation to their characters. of 22reproductive, immune and cell-to-cell communicative roles [23]. As recommended by the International Union of Pure and Applied Chemistry (IUPAC), fucoidans is a general term used to describe sulfated L-fucose-based polymers including sulfated fucans cited by the Swedish scholar Kylin, as well as other fucose-rich sulfated heteropolysaccharides [23,28]. Their chemical structures, in terms of monomeric composition and branching, are quite simple in marine invertebrates compared to their analogues in brown algae [13,29].Hundreds of articles have thoroughly discussed and reviewed the biological, pharmacological and pharmaceutical applications of fucoidans [30][31][32][33], including nanomedicine, [34] which has made it a hot topic in the last few decades [35][36][37]. All these studies tried to investigate fucoidans molecular mechanisms in relation to their chemical structure and physicochemical properties. Therefore, different hypotheses were suggested for each activity, such as anti-tumor [31,[38][39][40], anti-coagulant [41,42], anti-viral [43,44] and anti-inflammatory activity [45,46]. These investigations revealed that various factors are relevant, such as molecular weight, sulfation pattern, sulfate content and monomeric composition [47][48][49]. For example, different fractions were produced with different physicochemical properties in our previous experiments; sulfation pattern and sulfate content were highly related to anti-viral and cytotoxic activities against HSV-1 and Caco-2 cell lines, respectively, while molecular weight and sugar composition were potential factors in anti-coagulation activity [41,50]. In addition, degree of purity was reported as an influential factor [32], where co-extracted contaminants (e.g., phlorotannins or polyphenols) could lead to significant interference in anti-oxidant activity and, consequently, cosmetic applications [51,52].Therefore, several key production challenges regarding fucoidans were discussed in our last review article in order to obtain a product that follows the universal good manufactured practice (GMP) guidelines. The article discussed sources of heterogeneity in extracted fucoidans, including the different biotic (e.g., biogenic, geographical and seas...

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“…The M w value of JSP remained lower than those reported for sulfated xylogalactans extracted from calcareous red algae of the family Corallinaceae, such as C. officinalis, B. orbigniana and J. rubens [3,14]. The presence of short chains in the JSP structure could also decrease the M n value and consequently increase the polydispersity [55,56]. Note that further purification steps could be done in the future to eliminate the Glc-storage contamination and enhance the structural characterization of this xylogalactan.…”

Section: Macromolecular Characteristics Of Jspmentioning

confidence: 99%

“…The [η] of 76 mL/g and the hydrodynamic radius R h of 16.8 nm obtained for JSP suggest a flexible random coil conformation with a value of Mark-Houwink-Sakurada exponent α ranging between 0.5 and 0.8. [33,49,56]. Finally, the theoretical critical concentration C* of JSP, which can be obtained by ks/[η] (with ks = 0,5 to 1 for coil polysaccharides in water) could range from 6.5 to 13.1 g/L.…”

Section: Macromolecular Characteristics Of Jspmentioning

confidence: 99%

Structural Features and Rheological Properties of a Sulfated Xylogalactan-Rich Fraction Isolated from Tunisian Red Seaweed Jania adhaerens

et al. 2020

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A novel sulfated xylogalactan-rich fraction (JSP for J. adhaerens Sulfated Polysaccharide) was extracted from the red Tunisian seaweed Jania adhaerens. JSP was purified using an alcoholic precipitation process and characterized by Attenuated Total Reflectance-Fourier-transform infrared spectroscopy (ATR-FTIR), high-pressure size exclusion chromatography (HPSEC) with a multi-angle laser light scattering (MALLS), gas chromatography coupled to mass spectrometry (GC-MS) and nuclear magnetic resonance spectroscopy (NMR, 1D and 2D). JSP was then evaluated regarding its physicochemical and rheological properties. Results showed that JSP was mainly composed of an agar-like xylogalactan sharing the general characteristics of corallinans. The structure of JSP was mainly composed of agaran disaccharidic repeating units (→3)-β-d-Galp-(1,4)-α-l-Galp-(1→) n and (→3)-β-d-Galp-(1,4)-3,6-α-l-AnGalp-(1→) n , mainly substituted on O-6 of (1,3)-β-d-Galp residues by β-xylosyl side chains, and less with sulfate or methoxy groups. (1,4)-α-l-Galp residues were also substituted by methoxy and/or sulfate groups in the O-2 and O-3 positions. Mass-average and number-average molecular masses (M w ) and (M n ), intrinsic viscosity ([η]) and hydrodynamic radius (R h ) for JSP were, respectively, 8.0 × 10 5 g/mol, 1.0 × 10 5 g/mol, 76 mL/g and 16.8 nm, showing a flexible random coil conformation in solution. The critical overlap concentration C* of JSP was evaluated at 7.5 g/L using the Williamson model. In the semi-diluted regime, JSP solutions displayed a shear-thinning behavior with a great viscoelasticity character influenced by temperature and monovalent salts. The flow characteristics of JSP were described by the Ostwald model. always belongs to the d-series, while the former (α-Gal) can occur as d-(carrageenans) or l-(agarans) series [4][5][6][7]. The main backbone can be substituted by pyruvic acid ketals, sulfate, O-glycosyl and/or methyl groups and also by side chains, giving rise to great structural changes along the galactan chain. These structural changes affect the physicochemical and rheological behaviors of these polymers. So far, it has been reported that sulfated galactans exhibit numerous biological properties, including antioxidant, anticoagulant, antinociceptive, immunomodulatory, anticancer, gastroprotective, anti-inflammatory, antithrombotic and antiproliferative [1,[6][7][8][9][10][11][12][13][14]. Marine seaweed (Phaeophyceae and Rhodophyceae) cell wall polysaccharides also hold great promise as a raw material for feed, food, and biofuel production. Through metabolic engineering, seaweeds (micro-and macroalgae) are attracting growing attention as an alternative source of biofuel by converting the seaweed biomass and, in particular, the cell wall, which is rich in carbohydrates, into liquid biofuels [15].Galactans are currently used as thickening, gelling, and stabilizing agents in food, cosmetic, and pharmaceutical fields [1,10-16]. However, sulfated galactans produced by Corallinales are less studied, probably because ...

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Physico-chemical characterization and pharmacological evaluation of sulfated polysaccharides from three species of Mediterranean brown algae of the genus Cystoseira

Cited by 75 publications

References 29 publications

Prediction of new Hsp90 inhibitors based on 3,4-isoxazolediamide scaffold using QSAR study, molecular docking and molecular dynamic simulation

Prediction of new Hsp90 inhibitors based on 3,4-isoxazolediamide scaffold using QSAR study, molecular docking and molecular dynamic simulation

Fucoidans: Downstream Processes and Recent Applications

Structural Features and Rheological Properties of a Sulfated Xylogalactan-Rich Fraction Isolated from Tunisian Red Seaweed Jania adhaerens

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