Design and syntheses of mono and multivalent mannosyl-lipoconjugates for targeted liposomal drug delivery

Štimac, Adela; Cvitaš, Jelena TrmL·iL·; Frkanec, Leo; Frkanec, Ruža

doi:10.1016/j.ijpharm.2016.06.123

Cited by 14 publications

(18 citation statements)

References 55 publications

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“…[33] Monovalent, 1, divalent, 2, and tetravalent, 3, mannosyllipoconjugates were prepared as previously described (Figure 2). [31] Chromatographic analysis were carried out using the Waters HPLC System equipped with 2996 PDA detector and Empower software (Milford, MA, USA). LiChrosorb RP-18 (5 μm), 4 × 250 mm (Merck) and TSK-gel G300SW 7,5 mm × 60 cm (Tosoh Biosciences), columns for HPLC analyses were used.…”

Section: Methodsmentioning

confidence: 99%

“…[31,34] Briefly, eggphosphatidylcholine, cholesterol and mannosyl-lypoconjugates (1, 2 or 3) in a molar ratio of 7 : 5 : 0,5 were dissolved in chloroform : methanol (2 : 1). The chloroform and methanol were evaporated to dryness under vacuum on a rotary evaporator, and then lipid film was hydrated with OVA in saline, concentration 1 mg/mL by gentle hand shaking.…”

Section: Preparation Of Mannosylated Liposomes Formulationsmentioning

confidence: 99%

“…Chemical synthesis, purification and characterization of such amphiphilic compounds is a very complex process. [17] Synthesis of new glycosyl lipoconjugates provides many advantages with respect to the design of carbohydrate ligands having specific structural characteristics and their binding on different lipophilic anchors such as fatty acids [31] and cholesterol. [42] In our previous research, we have shown how adamantane can be used as a membrane anchor in lipid bilayer for different carbohydrate molecules which are exposed on liposome surface.…”

Section: Preparation Of Mannosylated Liposomesmentioning

confidence: 99%

“…[30,43] The obtained results have confirmed that Con A successfully recognized mannosyl ligands exposed on liposome surface and exhibits higher affinity to multivalent mannosyl ligands. [31] Here, we report preparation and characterization of mannosylated liposomes with/without built-in peptidoglycan based immunomodulators, PGM or Ad2TP2, and with entrapped model antigen, ovalbumin. The mannosylated liposomes were prepared in two ways, by incorporation of synthetic mono-, di-and tetramannosyl-lipoconjugates (1, 2, 3) into the lipid bilayer of liposomes or by covalent attachment of p-aminophenyl-α-D-mannopyranoside to the preformed liposomes.…”

Section: Preparation Of Mannosylated Liposomesmentioning

confidence: 99%

“…[28][29][30] In recently published paper we described the synthesis of mono-, di-and tetramannosyllipoconjugate, used for mannosylation of liposomes, and studies of interaction of prepared mannosylated liposomes with model lectine, concanavaline A (Con A) by quartz crystal microbalance (QCM). [31] Here we report preparation of mannosylated liposomes with built-in peptidoglycan based immunomodulators, peptidoglycan monomer surface. Mannosylated liposome formulations of antigen with built-in immunomodulators were characterized and their adjuvant effect was tested.…”

mentioning

confidence: 99%

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Mannosylated Liposomes with Built-in Peptidoglycan Based Immunomodulators for Subunit Vaccine Formulations

Štimac¹,

Bendelja²,

Sikirić³

et al. 2017

Croat. Chem. Acta

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The aim of the present study is preparation of mannosylated liposomes with built-in small molecule immunopotentiators for targeted, receptors mediated, delivery of antigens. The liposomes were mannosylated in two ways, by covalent attachment of p-aminophenyl-α-Dmannopyranoside to the preformed liposomes and by incorporation of synthetic mono-, di-and tetramannosyl-lipoconjugates into the lipid bilayer of liposomes. Four different mannosylated liposome formulations with incorporated model antigen, ovalbumin (OVA), and immunomodulators, PGM and Ad2TP2, were prepared and characterized. The influence of mannosylated liposome formulations on the antigen-specific humoral immune response was investigated. It has been shown that mannosylated liposomal formulations did not enhance the humoral immune response and production of anti-OVA antibodies but they significantly affected the type of OVA specific immune reaction and directed it towards Th1 type.

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Section: Methodsmentioning

confidence: 99%

Section: Preparation Of Mannosylated Liposomes Formulationsmentioning

confidence: 99%

Section: Preparation Of Mannosylated Liposomesmentioning

confidence: 99%

Section: Preparation Of Mannosylated Liposomesmentioning

confidence: 99%

mentioning

confidence: 99%

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Mannosylated Liposomes with Built-in Peptidoglycan Based Immunomodulators for Subunit Vaccine Formulations

Štimac¹,

Bendelja²,

Sikirić³

et al. 2017

Croat. Chem. Acta

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Analysis of Carbohydrates and Glycoconjugates by Matrix‐assisted Laser Desorption/Ionization Mass Spectrometry: An Update for 2015–2016

Harvey

2021

Mass Spectrometry Reviews

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This review is the ninth update of the original article published in 1999 on the application of matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2016. Also included are papers that describe methods appropriate to analysis by MALDI, such as sample preparation techniques, even though the ionization method is not MALDI. Topics covered in the first part of the review include general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation and arrays. The second part of the review is devoted to applications to various structural types such as oligo‐ and poly‐saccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals. Much of this material is presented in tabular form. The third part of the review covers medical and industrial applications of the technique, studies of enzyme reactions and applications to chemical synthesis. The reported work shows increasing use of combined new techniques such as ion mobility and the enormous impact that MALDI imaging is having. MALDI, although invented over 30 years ago is still an ideal technique for carbohydrate analysis and advancements in the technique and range of applications show no sign of deminishing. © 2020 Wiley Periodicals, Inc.

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Applications of mannose-binding lectins and mannan glycoconjugates in nanomedicine

Gupta

2022

J Nanopart Res

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Glycosylated nanoparticles (NPs) have drawn a lot of attention in the biomedical field over the past few decades, particularly in applications like targeted drug delivery. Mannosylated NPs and mannan-binding lectins/proteins (MBL/MBP) are emerging as promising tools for delivery of drugs, medicines, and enzymes to targeted tissues and cells as nanocarriers, enhancing their therapeutic benefits while avoiding the adverse effects of the drug. The occurrence of plenty of lectin receptors and their mannan ligands on cell surfaces makes them multifaceted carriers appropriate for specific delivery of bioactive drug materials to their targeted sites. Thus, the present review describes the tethering of mannose (Man) to several nanostructures, like micelles, liposomes, and other NPs, applicable for drug delivery systems. Bioadhesion through MBL-like receptors on cells has involvements applicable to additional arenas of science, for example gene delivery, tissue engineering, biomaterials, and nanotechnology. This review also focuses on the role of various aspects of drug/antigen delivery using (i) mannosylated NPs, (ii) mannosylated lectins, (iii) amphiphilic glycopolymer NPs, and (iv) natural mannan-containing polysaccharides, with most significant applications of MBL-based NPs as multivalent scaffolds, using different strategies. Graphical abstract Mannosylated NPs and/or MBL/MBP are coming up as viable and versatile tools as nanocarriers to deliver drugs and enzymes precisely to their target tissues or cells. The presence of abundant number of lectin receptors and their mannan ligands on cell surfaces makes them versatile carriers suitable for the targeted delivery of bioactive drugs.

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Design and syntheses of mono and multivalent mannosyl-lipoconjugates for targeted liposomal drug delivery

Cited by 14 publications

References 55 publications

Mannosylated Liposomes with Built-in Peptidoglycan Based Immunomodulators for Subunit Vaccine Formulations

Mannosylated Liposomes with Built-in Peptidoglycan Based Immunomodulators for Subunit Vaccine Formulations

Analysis of Carbohydrates and Glycoconjugates by Matrix‐assisted Laser Desorption/Ionization Mass Spectrometry: An Update for 2015–2016

Applications of mannose-binding lectins and mannan glycoconjugates in nanomedicine

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