Folate-decorated carboxymethyl cellulose for controlled doxorubicin delivery

Movagharnezhad, Nasim; Moghadam, Peyman Najafi

doi:10.1007/s00396-015-3768-4

Cited by 21 publications

(10 citation statements)

References 32 publications

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“…Nevertheless, the lack of solubility of CMC in organic solvents, under both its sodium salt (NaCMC) and acid (HCMC) form, significantly limits its derivatization by grafting of hydrophobic molecules. Currently, only few strategies allow for the covalent grafting of hydrophobic moieties onto CMC, involving either the dispersion of the polysaccharide in organic solvent [11,12,13,14,15,16,17,18] or its previous modification (i.e., ion exchange to obtain the tetrabutylammonium (TBA) salt) [19,20,21] to form an organo-soluble derivative. Another possibility is represented by the condensation of CMC with an amine, at high temperature and in heterogeneous conditions, which results in the elimination of water and formation of an amide bond [22,23].…”

Section: Introductionmentioning

confidence: 99%

Solvent-Free Synthesis of Amidated Carboxymethyl Cellulose Derivatives: Effect on the Thermal Properties

2019

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The present work explores the possibility of chemically modifying carboxymethyl cellulose (CMC), a widely diffused commercial cellulose ether, by grafting of hydrophobic moieties. Amidation of CMC, at high temperature and in heterogeneous conditions, was selected as synthetic tool for grafting on CMC a panel of commercially available amines (bearing long aliphatic chains, alkyl aromatic and heteroaromatic groups, more or less spaced from the cellulose backbone). The reaction was successfully carried out in absence of solvents, catalysts and coupling agents, providing a promising and more sustainable alternative to conventional amidation procedures. Relationships between the chemical structure of the obtained CMC derivatives and their thermal properties were carefully studied, with a particular attention to the thermal behavior. Grafting of aromatic and heteroaromatic alkyl amines, presenting a linear alkyl chain between CMC backbone and a terminal bulky moiety, allowed for efficiently separating the polysaccharide chains, improving their mobility and resulting in a consequent lowering of the glass transition temperature (Tg). The Tg values obtained (90–147 °C) were found to be closely dependent on both the size of the aliphatic spacer, the structure of the aromatic ring and the extent of amidation.

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Section: Introductionmentioning

confidence: 99%

Solvent-Free Synthesis of Amidated Carboxymethyl Cellulose Derivatives: Effect on the Thermal Properties

2019

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“…In addition, CMC has been proven to possess good biocompatibility and thus it is a promising material for biomedical applications. CMC is a water-soluble polysaccharide in practically the full range of pH from acidic to alkaline solutions, including at physiological conditions, possessing both carboxylate and hydroxyl groups that allow this multifunctional macromolecule to exert strong interactions with drug molecules. ,, …”

Section: Introductionmentioning

confidence: 99%

Design and Development of Polysaccharide-Doxorubicin-Peptide Bioconjugates for Dual Synergistic Effects of Integrin-Targeted and Cell-Penetrating Peptides for Cancer Chemotherapy

et al. 2018

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Polymer-drug conjugation is an attractive approach for target delivering insoluble and highly toxic drugs to tumor sites to overcome the side-effects caused by cancer chemotherapy. In this study we designed and synthesized novel polymer-drug-peptide conjugates for improved specificity on targeting cancer cells. Chemically modified polysaccharide, carboxymethylcellulose (CMC), was conjugated with doxorubicin (DOX) anticancer drug by amide bonds and dually biofunctionalized with integrin-target receptor tripeptide (RGD) and l-arginine (R) as cell-penetrating amino acid for synergistic targeting and enhancing internalization by cancer cells. These bioconjugates were tested as prodrugs against bone, breast, and brain cancer cell lines (SAOS, MCF7, and U87) and a normal cell line (HEK 293T, reference). The physicochemical characterization showed the formation of amide bonds between carboxylates (-RCOO) from CMC biopolymer and amino groups (-NH) from DOX and peptides (RGD or R). Moreover, these polymer-drug-peptide bioconjugates formed nanoparticulate colloidal structures and behaved as "smart" drug delivery systems (DDS) promoting remarkable reduction of the cytotoxicity toward normal cells (HEK 293T) while retaining high killing activity against cancer cells. Based on cell viability bioassays, DNA-staining, and confocal laser microscopy, this effect was assigned to the association of physicochemical aspects with the difference of the endocytic pathways and the drug release rates in live cells caused by the biofunctionalization of the macromolecule-drug systems with RGD and l-arginine. In addition, chick chorioallantoic membrane (CAM) assay was performed as an in vivo xenograft model test, which endorsed the in vitro results of anticancer activities of these polymer-drug systems. Thus, prodrug nanocarriers based on CMC-DOX-peptide bioconjugates were developed for simultaneously integrin-targeting and high killing efficacy against cancer cells, while preserving healthy cells with promising perspectives in cancer chemotherapy.

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“…Comparing the spectrum of pure succinic acid and that of SDH, it is remarked that the characteristic peak at 3400 cm -1 due to NH 2 appears in dihydrazide, while the peak at 3000 cm -1 in succinic acid is due to OH. 8 The bands at 1690 cm -1 and 1413 cm -1 are due to C=O and COO symmetric stretch in succinic acid. The bands at 1550 and 1403 cm -1 correspond to the amide group C=O and C-N in SDH.…”

Section: Preparation Of Sdhmentioning

confidence: 99%

“…The characteristic peak at 1630 cm -1 is due to the introduction of C=N in DCMC/NCMC. 8 In the spectra of DCMC, the peak at 800 cm -1 belonging to hemiacetal disappeared because the C=O of DCMC was not available any more.…”

Section: Reaction Of Dcmc With Ncmcmentioning

confidence: 99%

“…7 Also, CMC can be modified into a new carboxymethyl cellulose hydrazide (NCMC) by the reaction with hydrazine hydrate to introduce the NH-NH 2 group. 8 The formation of the hydrazone bond (Schiff base) via the reaction of an aldehyde functionalized substrate, such as DCMC and hydrazide, enhancing the antimicrobial activity of the substrate. 9,10 The aim of this study was to prepare antimicrobial compounds based on cellulose extracted from destoned (husk portion) of olive oil waste.…”

Section: Introductionmentioning

confidence: 99%

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Functionalization and Cross-Linking of Carboxymethyl Cellulose in Aqueous Media

Dacrory¹,

Abou-Yousef²,

Kamel³

et al. 2019

Cellulose Chem. Technol.

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Lignocelluloses are the main components of the wastes of olive oil industrial production. Partially destoned olive wastes contain a small amount of oil and water. So, olive wastes should have lower fiber content in comparison with crude olive waste. Functionalization of cellulose extracted from olive wastes enhances its importance for production of antimicrobial materials. In this work, dialdehyde carboxymethyl cellulose (DCMC), as cross-linking agent, was successfully prepared by using periodate oxidation of carboxymethyl cellulose (CMC), which had been previously prepared from olive oil by-products. CMC was modified with hydrazine monohydrate in order to prepare carboxymethyl hydrazide (NCMC), which was reacted with DCMC through Schiff's base reaction, resulting in crosslinking of NCMC. Also, DCMC was reacted with succinic dihydrazide (SDH) through Schiff's base reaction to give CMCSH. The water uptake of the prepared samples was also studied. All the modifications and reactions were confirmed by Fourier Transform Infrared Spectroscopy (FTIR), Scanning Electron Microscopy (SEM) and Transmission Electron Microscopy (TEM). Silver nanoparticles (AgNPs) were loaded onto the prepared cross-linked compounds and their loading was confirmed by EDX. The antimicrobial activities of the silver-loaded cross-linked compounds were investigated against gram-positive and gram-negative bacteria, as well as against yeasts.

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Folate-decorated carboxymethyl cellulose for controlled doxorubicin delivery

Cited by 21 publications

References 32 publications

Solvent-Free Synthesis of Amidated Carboxymethyl Cellulose Derivatives: Effect on the Thermal Properties

Solvent-Free Synthesis of Amidated Carboxymethyl Cellulose Derivatives: Effect on the Thermal Properties

Design and Development of Polysaccharide-Doxorubicin-Peptide Bioconjugates for Dual Synergistic Effects of Integrin-Targeted and Cell-Penetrating Peptides for Cancer Chemotherapy

Functionalization and Cross-Linking of Carboxymethyl Cellulose in Aqueous Media

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