Molecular dynamics study on the interaction between doxorubicin and hydrophobically modified chitosan oligosaccharide

Shan, Peng; Shen, Jia-Wei; Xu, Dong; Shi, Liyun; Gao, Jie; Lan, Ya-Wei; Wang, Qi; Wei, Xiao-Hong

doi:10.1039/c4ra01199f

Cited by 29 publications

(16 citation statements)

References 35 publications

(31 reference statements)

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“…A characteristic peak at 3.85 Å is observed for all models at both temperatures signifying evident stacking. This distance is close to the one reported previously, bearing in mind that in our case, it is a COM‐COM and not an interplane separation. The high‐intensity peaks indicate a particular adsorption position, and the low broad peaks at remote distances correspond to spatial proximity or long‐range interactions in the course of the trajectory.…”

Section: Resultssupporting

confidence: 91%

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Characterization of the interaction forces in a drug carrier complex of doxorubicin with a drug‐binding peptide

et al. 2017

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Polypeptide-based materials are used as building blocks for drug delivery systems aimed at toxicity decrease in chemotherapeutics. A molecular-level approach is adopted for investigating the non-covalent interactions between doxorubicin and a recently synthesized drug-binging peptide as a key part of a system for delivery to neoplastic cells. Molecular dynamics simulations in aqueous solution at room and body temperature are applied to investigate the structure and the binding modes within the drug-peptide complex. The tryptophans are outlined as the main chemotherapeutic adsorption sites, and the importance of their placement in the peptide sequence is highlighted. The drug-peptide binging energy is evaluated by density functional theory calculations. Principal component analysis reveals comparable importance of several types of interaction for the binding strength. π-Stacking is dominant, but other factors are also significant: intercalation, peptide backbone stacking, electrostatics, dispersion, and solvation. Intra- and intermolecular H-bonding also stabilizes the complexes. The influence of solvent molecules on the binding energy is mild. The obtained data characterize the drug-to-peptide attachment as a mainly attractive collective process with interactions spanning a broad range of values. These results explain with atomistic detail the experimentally registered doxorubicin-binging ability of the peptide and outline the complex as a prospective carrying unit that can be employed in design of drug delivery systems.

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Section: Resultssupporting

confidence: 91%

“…As far as theoretical calculations of drug–peptide‐based complexes are concerned, Shan et al . carry out MD simulations in aqueous solution at 27°C to reveal the interactions between DOX and a hexamer of chitosan oligosaccharide (COS) modified with hydrophobic acids.…”

Section: Introductionmentioning

confidence: 99%

Characterization of the interaction forces in a drug carrier complex of doxorubicin with a drug‐binding peptide

et al. 2017

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“…In recent years, natural polysaccharides have been extensively studied for hydrophobic modification and formation of self-assembled nanoparticles, due to their biodegradability (Chen et al 2011), biocompatibility (Guo et al 2012) and solubilization property (Chen et al 2015). Some polysaccharides, including chitosan (Hu et al 2008, Shan et al 2014, hyaluronic acid, pullulan (Sallustio et al 2004), heparin, and starch (Namazia et al 2011), have been reported on their chemical modifications by grafting hydrophobic groups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, self-assembly, and in vitro toxicity of fatty acids-modified Bletilla striata polysaccharide

Wang

Hong³

et al. 2016

Artificial Cells, Nanomedicine, and Biotechnology

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Hydrophobic modification of Bletilla striata polysaccharide (BSP) was performed by grafting fatty acids to BSP backbone and then characterized on their physicochemical properties. All neutral derivatives were able to self-assemble into spherical particles within the size range of 250-400 nm, their size and critical micelle concentration decreased with increasing hydrophobicity and substitution degree of the fatty acids. Also, the BSP-stearic acid conjugates showed a preferable performance on hemolysis test and cytotoxicity analysis on HepG2 cells, which suggested their potential application as a drug delivery vector.

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“…(1) behavior of the nanoparticle in the bloodstream and the protective polymer corona, (2) drug loading and release and (3) nanoparticle interaction with lipid membranes and entry into the cell. We would like to here alert the reader to the fact that there are other reviews of aspects of the use of computational Drugs, theirs applications, and references 5-flouracil -anti-cancer drug (Barraza et al, 2015;Kacar, 2019) Albendazole -anti-worm drug (Rodríguez-Hidalgo et al, 2011) Amphotercin B -antifungal drugs (Mobasheri et al, 2016) Anakinra -used in arthritis therapy (Liebner et al, 2014) Camptothecin -chemotherapy agent (Ansari et al, 2018;Alinejad et al, 2020) Carmustine -chemotherapy agent (Wolski et al, 2017a;Mortazavifar et al, 2019) Chlortetracycline -antibiotic (Dowlatabadi et al, 2019) Cisplatin -chemotherapy agent (Panczyk et al, 2013) Curcurbitacin drug families (Patel et al, 2010a) Cyclosporine -immunosuppressant (Tokarský et al, 2011) Dicolofenac -anti-inflammatory agents (Karjiban et al, 2012) Doxorubicin -chemotherapy agent (Guo et al, 2010(Guo et al, , 2012bYang et al, 2012;Yang C. et al, 2019;Yang Y.-L. et al, 2019;Zhang et al, 2012Zhang et al, , 2014Zhang et al, , 2018Nie et al, 2013;Shan et al, 2014;Izadyar et al, 2016;Rungrotmongkol and Poo-arporn, 2016;Wolski et al, 2017bWolski et al, , 2018Wolski et al, , 2019Hu et al, 2017;Mousavi et al, 2018;Kordzadeh et al, 2019;Alinejad et al, 2020;Exner and Ivanova, 2020;…”

Section: Molecular Dynamics Simulation Applied To Nanomedicinementioning

confidence: 99%

Mechanistic Understanding From Molecular Dynamics Simulation in Pharmaceutical Research 1: Drug Delivery

Bunker

Róg

2020

Front. Mol. Biosci.

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In this review, we outline the growing role that molecular dynamics simulation is able to play as a design tool in drug delivery. We cover both the pharmaceutical and computational backgrounds, in a pedagogical fashion, as this review is designed to be equally accessible to pharmaceutical researchers interested in what this new computational tool is capable of and experts in molecular modeling who wish to pursue pharmaceutical applications as a context for their research. The field has become too broad for us to concisely describe all work that has been carried out; many comprehensive reviews on subtopics of this area are cited. We discuss the insight molecular dynamics modeling has provided in dissolution and solubility, however, the majority of the discussion is focused on nanomedicine: the development of nanoscale drug delivery vehicles. Here we focus on three areas where molecular dynamics modeling has had a particularly strong impact: (1) behavior in the bloodstream and protective polymer corona, (2) Drug loading and controlled release, and (3) Nanoparticle interaction with both model and biological membranes. We conclude with some thoughts on the role that molecular dynamics simulation can grow to play in the development of new drug delivery systems.

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Molecular dynamics study on the interaction between doxorubicin and hydrophobically modified chitosan oligosaccharide

Abstract: Both π–π interactions and hydrophobic interactions were found to be essential for the loading of doxorubicin on hydrophobically modified chitosan oligosaccharides.

Cited by 29 publications

References 35 publications

Characterization of the interaction forces in a drug carrier complex of doxorubicin with a drug‐binding peptide

Characterization of the interaction forces in a drug carrier complex of doxorubicin with a drug‐binding peptide

Synthesis, self-assembly, and in vitro toxicity of fatty acids-modified Bletilla striata polysaccharide

Mechanistic Understanding From Molecular Dynamics Simulation in Pharmaceutical Research 1: Drug Delivery

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