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1.
Carbohydr Polym ; 261: 117847, 2021 Jun 01.
Article in English | MEDLINE | ID: mdl-33766343

ABSTRACT

Surface functionalization of mesoporous silica nanoparticles (MSNs) has been proposed as an efficient strategy for enhancing the biocompatibility and efficiency of an MSN-based carrier platform. Herein, natural polyelectrolyte multilayers composed of poly-l-ornithine (PLO) and carboxymethyl lentinan (LC) were coated on the surface of MSNs through a layer-by-layer (LbL) self-assembly technique, and were characterized by ζ-potential, FTIR, 13C NMR, SEM, TEM, XRD, and TG. The prepared carrier presented alternating positive and negative potentials when coated with the polyelectrolytes, and the surface of MSN-PLO/LC was rougher compared to the naked MSNs. The biocompatibility tests, including cytocompatibility, hemocompatibility, and histocompatibility, showed that MSNs biocompatibility could be improved by modifying LC. A high loading and sustained release drug delivery system was constructed after loading doxorubicin (DOX) into the prepared MSN-PLO/LC, which exhibited significant anti-proliferative efficiency in human cervical cancer cell lines (Hela). Therefore, the PLO/LC LbL NPs (layer-by-layer self-assembled nanoparticles coated with PLO/LC layers) based on MSNs, which is easily prepared by electrostatic interactions, can be considered a promising drug chemotherapeutic platform and delivery technique for future human cervical cancer therapy.


Subject(s)
Antineoplastic Agents/administration & dosage , Drug Carriers , Lentinan , Animals , Antineoplastic Agents/pharmacokinetics , Cells, Cultured , Drug Carriers/chemical synthesis , Drug Carriers/chemistry , Drug Carriers/therapeutic use , Drug Compounding , Drug Delivery Systems , Drug Liberation , Female , HeLa Cells , Humans , Lentinan/analogs & derivatives , Lentinan/chemical synthesis , Lentinan/chemistry , Lentinan/therapeutic use , Male , Materials Testing , Mice , Nanoparticles/chemistry , Nanoparticles/therapeutic use , Polymerization , Polymers/chemical synthesis , Polymers/chemistry , Polymers/therapeutic use , Porosity , Rabbits , Silicon Dioxide/chemistry , Xenograft Model Antitumor Assays
2.
Biosens Bioelectron ; 68: 72-77, 2015 Jun 15.
Article in English | MEDLINE | ID: mdl-25562733

ABSTRACT

Co-reactant electrochemiluminescence (ECL) is a simple and effective method for sensitive detection with amplified ECL signals. However, the intermolecular interaction between the luminescent reagents and their corresponding co-reactants, which is widely applied, has disadvantages in poor stability, low efficiency of electron transfer and relatively high loss of energy. In this work, an intramolecular self-enhanced ECL is proposed to settle this problem. Firstly, palladium nanowires (PdNWs) are synthesized with a green procedure in which Lentinan (LNT), one of ß-glucans with a triple helical conformation (t-LNT) in aqueous solution and single chains (s-LNT) at a temperature higher than 130°C, is used as stabilizer and reducing agent. The abtined PdNWs are applied to immobilize polyamidoamine (PAMAM) dendrimer which further reacts with tris (4, 4'-dicarboxylicacid-2, 2'-bipyridyl) ruthenium (II) dichloride to form a new electrochemiluminescent derivative (PdNWs-PAMAM-Ru). In this way, the Ru (II) luminophore and its co-reactive groups (amine groups in PAMAM) exist in the same complex, by which the electronic transmission distance is shortened and the luminous properties including stability and efficiency are enhanced. Moreover, due to the high specific surface areas and good electro-catalytic ability of PdNWs, the obtained PdNWs-PAMAM-Ru can be also applied to immobilize detection antibody (Ab2). Then, a sandwiched and sensitive ECL immunosensor is fabricated for the detection of carcinoembryonic antigen (CEA) with a wide linear ranged from 0.001 ng mL(-1) to 80 ng mL(-1) and a low detection limit of 0.3 pg mL(-1).


Subject(s)
Biosensing Techniques , Carcinoembryonic Antigen/isolation & purification , Nanowires/chemistry , Carcinoembryonic Antigen/chemistry , Dendrimers/chemistry , Gold/chemistry , Humans , Lentinan/chemical synthesis , Lentinan/chemistry , Limit of Detection , Metal Nanoparticles/chemistry , Palladium/chemistry , Ruthenium/chemistry , beta-Glucans/chemistry
3.
Carbohydr Res ; 342(3-4): 345-73, 2007 Feb 26.
Article in English | MEDLINE | ID: mdl-17109835

ABSTRACT

Formation of sugar-sugar orthoesters consisting of a fully acylated mono- or disaccharide donor and a partially protected mono- or disaccharide acceptor is regioselective, and rearrangement of the orthoesters via RO-(orthoester)C bond cleavage gives a dioxolenium ion intermediate leading to 1,2-trans glycosidic linkage. The activity order of hydroxyl groups in the partially protected mannose and glucose acceptors is 6-OH>3-OH>2- or 4-OH. The coupling reactions with acylated glycosyl trichloroacetimidates as the donors usually give orthoesters as the intermediates specially when the coupling is carried out at slowed rates, and this is successfully used in regio- and stereoselective syntheses of oligosaccharides. Mannose and rhamnose orthoesters readily undergo O-2-(orthoester)C bond breaking, and this is used for synthesis of alpha-(1-->2)-linked oligosaccharides. (1-->3)-Glucosylation is special since the rearrangement of its sugar orthoester intermediates can occur with either RO-(orthoester)C bond cleavage with formation of the dioxolenium ion leading to 1,2-trans linkage, or C-1-O-1 bond cleavage leading to 1,2-cis linkage, and this is dependent upon the structures of donor and acceptor that compose the orthoester.


Subject(s)
Oligosaccharides/chemical synthesis , Carbohydrate Sequence , Esters/chemistry , Glucose/analogs & derivatives , Glucose/chemistry , Lentinan/chemical synthesis , Mannose/analogs & derivatives , Mannose/chemistry , Molecular Sequence Data , Oligosaccharides, Branched-Chain/chemical synthesis , Rhamnose/analogs & derivatives , Rhamnose/chemistry
4.
Bioorg Med Chem ; 11(10): 2193-203, 2003 May 15.
Article in English | MEDLINE | ID: mdl-12713829

ABSTRACT

A beta-(1-->6)-branched beta-(1-->3)-glucohexaose, present in many biologically active polysaccharides from traditionally herbal medicines such as Ganoderma lucidum, Schizophyllum commune and Lentinus edodes, was synthesized as its lauryl glycoside 32, and its analogues 18, 20 and 33 containing an alpha-(1-->3) linked bond were synthesized. It is interesting to find that coupling of a 3,6-branched acylated trisaccharide trichloroacetimidate donor 9 with 3,6-branched acceptors 13 and 16 with 3'-OH gave the alpha-(1--> 3)-linked hexasaccharides 17 and 19, respectively, in spite of the presence of C-2 ester capable of neighboring group participation. However, coupling of 9 with 4-methoxyphenyl 4,6-O-benzylidene-beta-D-glucopyranoside (27) selectively gave beta-(1-->3)-linked tetrasaccharide 28. Simple chemical transformation of the tetrasaccharide 28 gave acylated tetrasaccharide trichloroacetimidate 29. Coupling of 29 with lauryl (1-->6)-linked disaccharide 26 with 3-OH gave beta-(1-->3)-linked hexasaccharide 30 as the major product. Bioassay showed that in combination with the chemotherapeutic agent cyclophospamide (CPA), the hexaose 18 at a dose of 0.5-1mg/kg substantially increased the inhibition of S(180) for CPA, but decreased the toxicity caused by CPA. Some of these oligosaccharides also inhibited U(14) noumenal tumor in mice effectively.


Subject(s)
Antineoplastic Agents/chemical synthesis , Lentinan/analogs & derivatives , Oligosaccharides/chemical synthesis , Allyl Compounds/chemistry , Animals , Antineoplastic Agents/pharmacology , Antineoplastic Agents/therapeutic use , Carbohydrate Sequence , Carcinoma, Ehrlich Tumor/drug therapy , Cell Line, Tumor , Cyclophosphamide/pharmacology , Cyclophosphamide/therapeutic use , Glycosides/chemistry , Lentinan/chemical synthesis , Lentinan/therapeutic use , Male , Mice , Molecular Conformation , Molecular Sequence Data , Stereoisomerism , Structure-Activity Relationship
5.
Jpn J Cancer Res ; 80(2): 95-8, 1989 Feb.
Article in English | MEDLINE | ID: mdl-2498253

ABSTRACT

Anti-HIV effects of lentinan sulfate were investigated by using an HTLV-I-carrying cell line, MT-4, in vitro. Lentinan, a fungal branched (1----3)-beta-D-glucan, was sulfated to various degrees by means of two kinds of procedures using piperidine N-sulfonic acid in dimethyl sulfoxide or chlorosulfonic acid in pyridine. Lentinan sulfate with a sulfur content of more than 13.9% effectively prevented HIV-induced cytopathic effects (CPE) at concentrations of more than 3.3 micrograms/ml. However, low-substituted lentinan sulfate did not prevent HIV-induced CPE at any concentration tested. When the countercation was 50% Na+ and 50% pyridinium ion, the inhibitory capacity was low. Anticoagulant activity of the lentinan sulfate was also assessed.


Subject(s)
Antiviral Agents/chemical synthesis , HIV/drug effects , Lentinan/chemical synthesis , Polysaccharides/chemical synthesis , Anticoagulants , Antiviral Agents/pharmacology , Cell Division/drug effects , Cell Line , Cytopathogenic Effect, Viral/drug effects , Fluorescent Antibody Technique , HIV Antigens/biosynthesis , Human T-lymphotropic virus 1 , Humans , Lentinan/analogs & derivatives , Lentinan/pharmacology , Lentinan/therapeutic use , Sulfur/metabolism
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