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A special issue of Pharmaceuticals (ISSN 1424-8247). This special issue belongs to the section "Pharmaceutical Technology".

Deadline for manuscript submissions: closed (15 October 2022) | Viewed by 57913

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Dr. Federica Sodano

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Department of Pharmacy, University of Naples Federico II, Via Domenico Montesano 49, 80131 Naples, Italy Department of Drug Science and Technology, University of Turin, Via Giuria 9, 10125 Turin, Italy
Interests: NO-donor; prodrug strategy; molecular hybrid design; drug design; drug delivery; drug targeting
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Dr. Maria Grazia Rimoli

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Department of Pharmacy, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy
Interests: prodrug strategy; carbohydrate-based prodrugs; drug targeting; drug discovery
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Special Issue Information

Dear Colleagues,

Carbohydrates are one of the four major classes of biomolecules; they play important roles in various biological processes, including inflammation and immune response, angiogenesis and metastasis of cancer cells, viral and bacterial infections, and many other cell–cell communications. The tremendous effort made by glycoscientists in recent decades have allowed carbohydrate-based drugs to pave the way for an anonymous area of the therapeutic world.

Medicinal chemists use carbohydrates, particularly mono- and disaccharides, as valuable carriers or key substructures in order to improve the pharmaceutical phase, pharmacokinetics and pharmacodynamics of well-known drugs. Resorting to the prodrug strategy or multitarget drugs, the conjugation of a traditional drug to carbohydrates allows many limitations of the parent drug to be overcome, such as lack of site of action specificity, toxicity, chemical instability. Additionally, carbohydrate-based nanosystems have been shown to better deliver the starting drug or generate selective targeting towards specific body districts, as well as improve the cellular permeability and toxicological profile of the parent drug.

In this Special Issue, "Carbohydrate-Based Drugs", we aim to collect both original articles and up-to-date reviews that focus on the design, synthesis and biological evaluations of novel carbohydrate-based drugs, with a focus on carbohydrate-based prodrugs and nanosystems.

As Guest Editors, we encourage researchers working in this area to contribute their recent studies to this Special Issue of Pharmaceuticals.

Dr. Federica Sodano
Dr. Maria Grazia Rimoli
Guest Editors

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Keywords

carbohydrates
carbohydrate hybrids
nanosystems
carbohydrate-based polymers
prodrugs
anti-inflammatory activity
antimicrobial activity
anticancer activity
pharmacokinetics profile
drug targeting
toxicity
biomedical applications

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Published Papers (12 papers)

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Research

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13 pages, 2097 KiB

Open AccessArticle

Effect of Agave Fructan Bioconjugates on Metabolic Syndrome Parameters in a Murine Model

by Eduardo Padilla-Camberos, Javier Arrizon and Georgina Sandoval

Pharmaceuticals 2023, 16(3), 412; https://doi.org/10.3390/ph16030412 - 8 Mar 2023

Cited by 5 | Viewed by 1823

Abstract

Metabolic syndrome is a complex disorder that combines abdominal obesity, dyslipidemia, hypertension, and insulin resistance. Metabolic syndrome affects 25% of the world’s population. Agave fructans have shown positive effects on alterations related to metabolic syndrome, so some investigations have focused on their bioconjugation with fatty acids to increase their biological activity. The objective of this work was to evaluate the effect of agave fructan bioconjugates in a rat model with metabolic syndrome. Agave fructans enzymatically bioconjugated (acylated via food-grade lipase catalysis) with propionate or laurate were administered orally for 8 weeks in rats fed a hypercaloric diet. Animals without treatment were used as the control group, as well as animals fed with a standard diet. The data indicate that the group of animals treated with laurate bioconjugates showed a significant decrease in glucose levels, systolic pressure, weight gain, and visceral adipose tissue, as well as a positive effect of pancreatic lipase inhibition. These results allow us to demonstrate the potential of agave bioconjugates, particularly laurate bioconjugates, for the prevention of diseases associated with metabolic syndrome. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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34 pages, 7191 KiB

Open AccessArticle

Mannosylated Polymeric Ligands for Targeted Delivery of Antibacterials and Their Adjuvants to Macrophages for the Enhancement of the Drug Efficiency

by Igor D. Zlotnikov, Alexander A. Ezhov, Rostislav A. Petrov, Maksim A. Vigovskiy, Olga A. Grigorieva, Natalya G. Belogurova and Elena V. Kudryashova

Pharmaceuticals 2022, 15(10), 1172; https://doi.org/10.3390/ph15101172 - 21 Sep 2022

Cited by 16 | Viewed by 2237

Abstract

Bacterial infections and especially resistant strains of pathogens localized in macrophages and granulomas are intractable diseases that pose a threat to millions of people. In this paper, the theoretical and experimental foundations for solving this problem are proposed due to two key aspects. The first is the use of a three-component polymer system for delivering fluoroquinolones to macrophages due to high-affinity interaction with mannose receptors (CD206). Cytometry assay determined that 95.5% macrophage-like cells were FITC-positive after adding high-affine to CD206 trimannoside conjugate HPCD-PEI1.8-triMan, and 61.7% were FITC-positive after adding medium-affine ligand with linear mannose label HPCD-PEI1.8-Man. The second aspect is the use of adjuvants, which are synergists for antibiotics. Using FTIR and NMR spectroscopy, it was shown that molecular containers, namely mannosylated polyethyleneimines (PEIs) and cyclodextrins (CDs), load moxifloxacin (MF) with dissociation constants of the order of 10⁻⁴–10⁻⁶ M; moreover, due to prolonged release and adsorption on the cell membrane, they enhance the effect of MF. Using CLSM, it was shown that eugenol (EG) increases the penetration of doxorubicin (Dox) into cells by an order of magnitude due to the creation of defects in the bacterial wall and the inhibition of efflux proteins. Fluorescence spectroscopy showed that 0.5% EG penetrates into bacteria and inhibits efflux proteins, which makes it possible to increase the maximum concentration of the antibiotic by 60% and maintain it for several hours until the pathogens are completely neutralized. Regulation of efflux is a possible way to overcome multiple drug resistance of both pathogens and cancer cells. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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21 pages, 2555 KiB

Open AccessArticle

Bacterial Cellulose—Adaptation of a Nature-Identical Material to the Needs of Advanced Chronic Wound Care

by Paul Zahel, Uwe Beekmann, Thomas Eberlein, Michael Schmitz, Oliver Werz and Dana Kralisch

Pharmaceuticals 2022, 15(6), 683; https://doi.org/10.3390/ph15060683 - 30 May 2022

Cited by 11 | Viewed by 3872

Abstract

Modern wound treatment calls for hydroactive dressings. Among the variety of materials that have entered the field of wound care in recent years, the carbohydrate polymer bacterial cellulose (BC) represents one of the most promising candidates as the biomaterial features a high moisture-loading and donation capacity, mechanical stability, moldability, and breathability. Although BC has already gained increasing relevance in the treatment of burn wounds, its potential and clinical performance for “chronic wound” indications have not yet been sufficiently investigated. This article focuses on experimental and clinical data regarding the application of BC within the indications of chronic, non-healing wounds, especially venous and diabetic ulcers. A recent clinical observation study in a chronic wound setting clearly demonstrated its wound-cleansing properties and ability to induce healing in stalling wounds. Furthermore, the material parameters of BC dressings obtained through the static cultivation of Komagataeibacter xylinus were investigated for the first time in standardized tests and compared to various advanced wound-care products. Surprisingly, a free swell absorptive capacity of a BC dressing variant containing 97% moisture was found, which was higher than that of alginate or even hydrofiber dressings. We hypothesize that the fine-structured, open porous network and the resulting capillary forces are among the main reasons for this unexpected result. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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32 pages, 4328 KiB

Open AccessArticle

Spectroscopy Approach for Highly-Efficient Screening of Lectin-Ligand Interactions in Application for Mannose Receptor and Molecular Containers for Antibacterial Drugs

by Igor D. Zlotnikov and Elena V. Kudryashova

Pharmaceuticals 2022, 15(5), 625; https://doi.org/10.3390/ph15050625 - 19 May 2022

Cited by 13 | Viewed by 2723

Abstract

Rational search of a ligand for a specific receptor is a cornerstone of a typical drug discovery process. However, to make it more “rational” one would appreciate having detailed information on the functional groups involved in ligand-receptor interaction. Typically, the 3D structure of a ligand-receptor complex can be built on the basis of time-consuming X-ray crystallography data. Here, a combination of FTIR and fluorescence methods, together with appropriate processing, yields valuable information about the functional groups of both the ligand and receptor involved in the interaction, with the simplicity of conventional spectrophotometry. We have synthesized the “molecular containers” based on cyclodextrins, polyethyleneimines (PEI) or spermine with mannose-rich side-chains of different molecular architecture (reticulated, star-shaped and branched) with variable parameters to facilitate delivery to alveolar macrophages. We have shown that synthetic mannose-rich conjugates are highly affine to the model mannose receptor ConA: K_d ≈ 10⁻⁵–10⁻⁷ M vs. natural ligand trimannoside (10⁻⁵ M). Further, it was shown that molecular containers effectively load levofloxacin (dissociation constants are 5·10⁻⁴–5·10⁻⁶ M) and the eugenol adjuvant (up to 15–80 drug molecules for each conjugate molecule) by including them in the cyclodextrins cavities, as well as by interacting with polymer chains. Promising formulations of levofloxacin and its enhancer (eugenol) in star-shaped and polymer conjugates of high capacity were obtained. UV spectroscopy demonstrated a doubling of the release time of levofloxacin into the external solution from the complexes with conjugates, and the effective action time (time of 80% release) was increased from 0.5 to 20–70 h. The synergy effect of antibacterial activity of levofloxacin and its adjuvants eugenol and apiol on Escherichia coli was demonstrated: the minimum effective concentration of the antibiotic was approximately halved. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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17 pages, 1987 KiB

Open AccessArticle

Galactosylated Prodrugs: A Strategy to Improve the Profile of Nonsteroidal Anti-Inflammatory Drugs

by Federica Sodano, Claudia Cristiano, Barbara Rolando, Elisabetta Marini, Loretta Lazzarato, Mariarosaria Cuozzo, Stefania Albrizio, Roberto Russo and Maria Grazia Rimoli

Pharmaceuticals 2022, 15(5), 552; https://doi.org/10.3390/ph15050552 - 29 Apr 2022

Cited by 7 | Viewed by 2413

Abstract

Carbohydrates are one of the most abundant and important classes of biomolecules. The variety in their structures makes them valuable carriers that can improve the pharmaceutical phase, pharmacokinetics and pharmacodynamics of well-known drugs. D-galactose is a simple, naturally occurring monosaccharide sugar that has been extensively studied for use as a carrier and has proven to be valuable in this role. With the aim of validating the galactose-prodrug approach, we have investigated the galactosylated prodrugs ibuprofen, ketoprofen, flurbiprofen and indomethacin, which we have named IbuGAL, OkyGAL, FluGAL and IndoGAL, respectively. Their physicochemical profiles in terms of lipophilicity, solubility and chemical stability have been evaluated at different physiological pH values, as have human serum stability and serum protein binding. Ex vivo intestinal permeation experiments were performed to provide preliminary insights into the oral bioavailability of the galactosylated prodrugs. Finally, their anti-inflammatory, analgesic and ulcerogenic activities were investigated in vivo in mice after oral treatment. The present results, taken together with those of previous studies, undoubtedly validate the galactosylated prodrug strategy as a problem-solving technique that can overcome the disadvantages of NSAIDs. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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26 pages, 10133 KiB

Open AccessArticle

A Lead-Based Fragment Library Screening of the Glycosyltransferase WaaG from Escherichia coli

by Federico Riu, Alessandro Ruda, Olof Engström, Claudio Muheim, Hani Mobarak, Jonas Ståhle, Paul Kosma, Antonio Carta, Daniel O. Daley and Göran Widmalm

Pharmaceuticals 2022, 15(2), 209; https://doi.org/10.3390/ph15020209 - 9 Feb 2022

Cited by 3 | Viewed by 2686

Abstract

Glucosyl transferase I (WaaG) in E. coli catalyzes the transfer of an α-d-glucosyl group to the inner core of the lipopolysaccharide (LPS) and plays an important role in the biogenesis of the outer membrane. If its activity could be inhibited, the integrity of the outer membrane would be compromised and the bacterium would be susceptible to antibiotics that are normally prevented from entering the cell. Herein, three libraries of molecules (A, B and C) were docked in the binding pocket of WaaG, utilizing the docking binding affinity as a filter to select fragment-based compounds for further investigations. From the results of the docking procedure, a selection of compounds was investigated by molecular dynamics (MD) simulations to obtain binding free energy (BFE) and K_D values for ligands as an evaluation for the binding to WaaG. Derivatives of 1,3-thiazoles (A7 and A4) from library A and 1,3,4-thiadiazole (B33) from library B displayed a promising profile of BFE, with K_D < mM, viz., 0.11, 0.62 and 0.04 mM, respectively. Further root-mean-square-deviation (RMSD), electrostatic/van der Waals contribution to the binding and H-bond interactions displayed a favorable profile for ligands A4 and B33. Mannose and/or heptose-containing disaccharides C1–C4, representing sub-structures of the inner core of the LPS, were also investigated by MD simulations, and compound C4²⁻ showed a calculated K_D = 0.4 µM. In the presence of UDP-Glc²⁻, the best-docked pose of disaccharide C4²⁻ is proximate to the glucose-binding site of WaaG. A study of the variation in angle and distance was performed on the different portions of WaaG (N-, the C- domains and the hinge region). The Spearman correlation coefficient between the two variables was close to unity, where both variables increase in the same way, suggesting a conformational rearrangement of the protein during the MD simulation, revealing molecular motions of the enzyme that may be part of the catalytic cycle. Selected compounds were also analyzed by Saturation Transfer Difference (STD) NMR experiments. STD effects were notable for the 1,3-thiazole derivatives A4, A8 and A15 with the apo form of the protein as well as in the presence of UDP for A4. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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18 pages, 56386 KiB

Open AccessArticle

Ketogal Safety Profile in Human Primary Colonic Epithelial Cells and in Mice

by Federica Sodano, Bice Avallone, Monica Tizzano, Chiara Fogliano, Barbara Rolando, Elena Gazzano, Chiara Riganti, Salvatore Magliocca, Mariarosaria Cuozzo, Stefania Albrizio, Antonio Calignano, Claudia Cristiano, Roberto Russo and Maria Grazia Rimoli

Pharmaceuticals 2021, 14(11), 1149; https://doi.org/10.3390/ph14111149 - 11 Nov 2021

Cited by 9 | Viewed by 2340

Abstract

In our previous studies, a ketorolac–galactose conjugate (ketogal) showed prolonged anti-inflammatory and analgesic activity, causing less gastric ulcerogenic effect and renal toxicity than its parent drug ketorolac. In order to demonstrate the safer profile of ketogal compared to ketorolac, histopathological changes in the small intestine and liver using three staining techniques before and after repeated oral administration in mice with ketorolac or an equimolecular dose of its galactosylated prodrug ketogal were assessed. Cytotoxicity and oxidative stress parameters were evaluated and compared in ketorolac- and ketogal-treated Human Primary Colonic Epithelial cells at different concentrations and incubation times. Evidence of mitochondrial oxidative stress was found after ketorolac treatment; this was attributable to altered mitochondrial membrane depolarization and oxidative stress parameters. No mitochondrial damage was observed after ketogal treatment. In ketorolac-treated mice, severe subepithelial vacuolation and erosion with inflammatory infiltrates and edematous area in the intestinal tissues were noted, as well as alterations in sinusoidal spaces and hepatocytes with foamy cytoplasm. In contrast, treatment with ketogal provided a significant improvement in the morphology of both organs. The prodrug clearly demonstrated a safer profile than its parent drug both in vitro and ex vivo, confirming that ketogal is a strategic alternative to ketorolac. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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Review

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26 pages, 10378 KiB

Open AccessReview

Therapeutic Targeting of TLR4 for Inflammation, Infection, and Cancer: A Perspective for Disaccharide Lipid A Mimetics

by Holger Heine and Alla Zamyatina

Pharmaceuticals 2023, 16(1), 23; https://doi.org/10.3390/ph16010023 - 23 Dec 2022

Cited by 26 | Viewed by 5683

Abstract

The Toll-like receptor 4 (TLR4) signaling pathway plays a central role in the prompt defense against infectious challenge and provides immediate response to Gram-negative bacterial infection. The TLR4/MD-2 complex can sense and respond to various pathogen-associated molecular patterns (PAMPs) with bacterial lipopolysaccharide (LPS) being the most potent and the most frequently occurring activator of the TLR4-mediated inflammation. TLR4 is believed to be both a friend and foe since improperly regulated TLR4 signaling can result in the overactivation of immune responses leading to sepsis, acute lung injury, or pathologic chronic inflammation involved in cancer and autoimmune disease. TLR4 is also considered a legitimate target for vaccine adjuvant development since its activation can boost the adaptive immune responses. The dual action of the TLR4 complex justifies the efforts in the development of both TLR4 antagonists as antisepsis drug candidates or remedies for chronic inflammatory diseases and TLR4 agonists as vaccine adjuvants or immunotherapeutics. In this review, we provide a brief overview of the biochemical evidences for possible pharmacologic applications of TLR4 ligands as therapeutics and report our systematic studies on the design, synthesis, and immunobiological evaluation of carbohydrate-based TLR4 antagonists with nanomolar affinity for MD-2 as well as disaccharide-based TLR4 agonists with picomolar affinity for the TLR4/MD-2 complex. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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38 pages, 12798 KiB

Open AccessReview

Antibiotics and Carbohydrate-Containing Drugs Targeting Bacterial Cell Envelopes: An Overview

by Federico Riu, Alessandro Ruda, Roberta Ibba, Simona Sestito, Ilenia Lupinu, Sandra Piras, Göran Widmalm and Antonio Carta

Pharmaceuticals 2022, 15(8), 942; https://doi.org/10.3390/ph15080942 - 29 Jul 2022

Cited by 19 | Viewed by 7650

Abstract

Certain bacteria constitute a threat to humans due to their ability to escape host defenses as they easily develop drug resistance. Bacteria are classified into gram-positive and gram-negative according to the composition of the cell membrane structure. Gram-negative bacteria have an additional outer membrane (OM) that is not present in their gram-positive counterpart; the latter instead hold a thicker peptidoglycan (PG) layer. This review covers the main structural and functional properties of cell wall polysaccharides (CWPs) and PG. Drugs targeting CWPs are discussed, both noncarbohydrate-related (β-lactams, fosfomycin, and lipopeptides) and carbohydrate-related (glycopeptides and lipoglycopeptides). Bacterial resistance to these drugs continues to evolve, which calls for novel antibacterial approaches to be developed. The use of carbohydrate-based vaccines as a valid strategy to prevent bacterial infections is also addressed. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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26 pages, 10154 KiB

Open AccessEditor’s ChoiceReview

GCase Enhancers: A Potential Therapeutic Option for Gaucher Disease and Other Neurological Disorders

by Macarena Martínez-Bailén, Francesca Clemente, Camilla Matassini and Francesca Cardona

Pharmaceuticals 2022, 15(7), 823; https://doi.org/10.3390/ph15070823 - 2 Jul 2022

Cited by 17 | Viewed by 5111

Abstract

Pharmaceutical chaperones (PCs) are small compounds able to bind and stabilize misfolded proteins, allowing them to recover their native folding and thus their biological activity. In particular, lysosomal storage disorders (LSDs), a class of metabolic disorders due to genetic mutations that result in misfolded lysosomal enzymes, can strongly benefit from the use of PCs able to facilitate their translocation to the lysosomes. This results in a recovery of their catalytic activity. No PC for the GCase enzyme (lysosomal acid-β-glucosidase, or glucocerebrosidase) has reached the market yet, despite the importance of this enzyme not only for Gaucher disease, the most common LSD, but also for neurological disorders, such as Parkinson’s disease. This review aims to describe the efforts made by the scientific community in the last 7 years (since 2015) in order to identify new PCs for the GCase enzyme, which have been mainly identified among glycomimetic-based compounds. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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44 pages, 3254 KiB

Open AccessReview

An Overview of Cellulose Derivatives-Based Dressings for Wound-Healing Management

by Elena-Emilia Tudoroiu, Cristina-Elena Dinu-Pîrvu, Mădălina Georgiana Albu Kaya, Lăcrămioara Popa, Valentina Anuța, Răzvan Mihai Prisada and Mihaela Violeta Ghica

Pharmaceuticals 2021, 14(12), 1215; https://doi.org/10.3390/ph14121215 - 24 Nov 2021

Cited by 79 | Viewed by 8224

Abstract

Presently, notwithstanding the progress regarding wound-healing management, the treatment of the majority of skin lesions still represents a serious challenge for biomedical and pharmaceutical industries. Thus, the attention of the researchers has turned to the development of novel materials based on cellulose derivatives. Cellulose derivatives are semi-synthetic biopolymers, which exhibit high solubility in water and represent an advantageous alternative to water-insoluble cellulose. These biopolymers possess excellent properties, such as biocompatibility, biodegradability, sustainability, non-toxicity, non-immunogenicity, thermo-gelling behavior, mechanical strength, abundance, low costs, antibacterial effect, and high hydrophilicity. They have an efficient ability to absorb and retain a large quantity of wound exudates in the interstitial sites of their networks and can maintain optimal local moisture. Cellulose derivatives also represent a proper scaffold to incorporate various bioactive agents with beneficial therapeutic effects on skin tissue restoration. Due to these suitable and versatile characteristics, cellulose derivatives are attractive and captivating materials for wound-healing applications. This review presents an extensive overview of recent research regarding promising cellulose derivatives-based materials for the development of multiple biomedical and pharmaceutical applications, such as wound dressings, drug delivery devices, and tissue engineering. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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37 pages, 6435 KiB

Open AccessReview

Inulin and Its Application in Drug Delivery

by Franklin Afinjuomo, Sadikalmahdi Abdella, Souha H. Youssef, Yunmei Song and Sanjay Garg

Pharmaceuticals 2021, 14(9), 855; https://doi.org/10.3390/ph14090855 - 26 Aug 2021

Cited by 46 | Viewed by 9404

Abstract

Inulin’s unique and flexible structure, stabilization/protective effects, and organ targeting ability make it an excellent drug delivery carrier compared to other biodegradable polysaccharides. The three hydroxyl groups attached to each fructose unit serve as an anchor for chemical modification. This, in turn, helps in increasing bioavailability, improving cellular uptake, and achieving targeted, sustained, and controlled release of drugs and biomolecules. This review focuses on the various types of inulin drug delivery systems such as hydrogel, conjugates, nanoparticles, microparticles, micelles, liposomes, complexes, prodrugs, and solid dispersion. The preparation and applications of the different inulin drug delivery systems are further discussed. This work highlights the fact that modification of inulin allows the use of this polymer as multifunctional scaffolds for different drug delivery systems. Full article

(This article belongs to the Special Issue Carbohydrate-Based Drugs)

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