Hemocompatible curcumin–dextran micelles as pH sensitive pro-drugs for enhanced therapeutic efficacy in cancer cells

Raveendran, Radhika; Bhuvaneshwar, G.S.; Sharma, Chandra P.

doi:10.1016/j.carbpol.2015.11.017

Cited by 74 publications

(27 citation statements)

References 47 publications

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“…The 1 H-NMR spectrum of HOOC-S-S-CUR, ALN-oHA and ALN-oHA-S-S-CUR are shown in Figure 3. The cur in ALN-oHA-S-S-CUR was seen in the region between 6.5 and 8 ppm [26], and the appearance of signal at peak 7.8 ppm was verified the amide bond (-CONH-) connection between ALN and oHA [16]. In addition, the -CH 2proton peak of 3,3-dithiodipropionic acid was seen at 2.8 ppm that accordance with its standard substance.…”

Section: Characterization Of Aln-oha-s-s-curmentioning

confidence: 58%

Multifunctional redox-responsive and CD44 receptor targeting polymer-drug nanomedicine based curcumin and alendronate: synthesis, characterization and in vitro evaluation

Dong

Zou

Guo

et al. 2017

Artificial Cells, Nanomedicine, and Biotechnology

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The traditional therapy of cancer has systemic side effects, and many cancers, such as human breast cancer and lung cancer easily metastasize to bones, leading to the formation of secondary tumours. This study was aimed at enhancing the anti-tumour effect of curcumin (CUR) and preventing tumour spread to the bone. A novel multifunctional redox-responsive and CD44 receptor targeting polymer-drug, poly alendronate-hyaluronan-S-S-curcumin copolymer (ALN-oHA-S-S-CUR) based CUR and alendronate (ALN) were synthesized successfully with the disulphide bond linker. The structure of ALN-oHA-S-S-CUR was characterized by H-NMR. The nanomedicine had natural anti-tumour drugs (CUR) as the hydrophobic kernel, and targeting CD44 receptor oligosaccharides of hyaluronan (oHA) and other anti-tumour drugs (ALN) as hydrophilic shell, named ALN-oHA-S-S-CUR conjugates, which could self-assemble into micelle-like nano-spheres in water via a dialysis method with hydrodynamic diameters of 179 ± 23 nm. Interestingly, the cur-loaded ALN-oHA-S-S-CUR micelles were stable in PBS but were capable of releasing the drug under the reducing environment. The rate of drug release was proportional to the GSH concentration. The uptake and cytotoxicity of micelles were higher in MDA-MB-231 cells than in MCF-7 cells because of a higher expression of the CD44 receptor in the former cell line. And compared to the cur-loaded oHA-CUR micelles, the cur-loaded ALN-oHA-S-S-CUR micelles had a good cellular uptake in 2D cancer cell and penetrability in 3D cancer cell spheroids. These results indicated the active targeting redox-sensitive micelles were promising as intracellular drug delivery systems for cancer treatment.

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Section: Characterization Of Aln-oha-s-s-curmentioning

confidence: 58%

Multifunctional redox-responsive and CD44 receptor targeting polymer-drug nanomedicine based curcumin and alendronate: synthesis, characterization and in vitro evaluation

Dong

Zou

Guo

et al. 2017

Artificial Cells, Nanomedicine, and Biotechnology

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“…Among various approaches, graft copolymerization is the easiest and less expensive way to introduce new functionalities without any loss in the properties of the supporting polysaccharide material [20]. Recent works reported that Cur conjugated with Dx is an effective anticancer pH sensitive pro drug [21].…”

Section: Introductionmentioning

confidence: 99%

“…is a Food and Drug Administration approved water soluble branched homo polysaccharide of glucose with α-1,6-linked D-glucopyranose linear chain and α-1,3-linkages as branches [20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Dextran based nanosized carrier for the controlled and targeted delivery of curcumin to liver cancer cells

Anirudhan

Binusreejayan

2016

International Journal of Biological Macromolecules

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“…A protonation of amide functions at pH = 4.3 was suspected to explain the pH driven release of the payload. According to a prodrug strategy, hydrophobic curcumin has also been conjugated to the hydrophilic backbone of dextran using acid labile succinate spacers or carbonate bonds . pH‐sensitive micelles based on acid‐labile Pluronic F68‐curcumin conjugates were also recently prepared with acid‐responsive cis ‐aconitic anhydride linkage…”

Section: Introductionmentioning

confidence: 99%

pH‐Sensitive Poly(ethylene glycol)/Poly(ethoxyethyl glycidyl ether) Block Copolymers: Synthesis, Characterization, Encapsulation, and Delivery of a Hydrophobic Drug

Illy

Zimbron

Molinié

et al. 2019

Macro Chemistry & Physics

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Curcumin is a natural polyphenolic compound known for its numerous pharmacological properties. However, its low water solubility and instability at neutral pH are serious drawbacks preventing its use as an oral drug. Well‐defined amphiphilic poly(ethylene glycol)‐block‐poly(ethoxyethyl glycidyl ether) (PEG‐b‐PEEGE) block copolymers carrying acid‐labile acetal groups are synthesized by anionic ring‐opening polymerization and investigated as potential pH‐sensitive nano‐carriers for delivery of curcumin to cancer cells. The nanoparticles, resulting from copolymer self‐assembly in aqueous media, are characterized by dynamic light scattering and cryo‐transmission electron microscopy. The nanoparticles’ stabilities are evaluated in three different phosphate buffers (pH = 7.2, 6.4, and 5.3). The stability decreases at lower pH and a complete disappearance of the nanoparticles is noticed after 4 days at pH 5.3. Curcumin is encapsulated in hydrophobic core of mPEG40‐b‐PEEGE25 nanoparticles allowing significant enhancements of curcumin solubility in water and lifetime at neutral pH. In vitro curcumin release is studied at different pH by UV‐spectroscopy and high‐performance liquid chromatography (HPLC). The cytotoxicity of curcumin and curcumin encapsulated in micelles is evaluated by cell viability 3‐(4,5‐Dimethyl‐2‐thiazolyl)‐2,5‐diphenyl‐2H‐tetrazolium bromide (MTT) assay on MDA‐MB‐231 human breast cancer cells.

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Hemocompatible curcumin–dextran micelles as pH sensitive pro-drugs for enhanced therapeutic efficacy in cancer cells

Cited by 74 publications

References 47 publications

Multifunctional redox-responsive and CD44 receptor targeting polymer-drug nanomedicine based curcumin and alendronate: synthesis, characterization and in vitro evaluation

Multifunctional redox-responsive and CD44 receptor targeting polymer-drug nanomedicine based curcumin and alendronate: synthesis, characterization and in vitro evaluation

Dextran based nanosized carrier for the controlled and targeted delivery of curcumin to liver cancer cells

pH‐Sensitive Poly(ethylene glycol)/Poly(ethoxyethyl glycidyl ether) Block Copolymers: Synthesis, Characterization, Encapsulation, and Delivery of a Hydrophobic Drug

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