Conjugation of curcumin onto alginate enhances aqueous solubility and stability of curcumin

Dey, Soma; Sreenivasan, K.

doi:10.1016/j.carbpol.2013.08.067

Cited by 146 publications

(54 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Therefore, particularly innovative nanoformulations have been developed to overcome these problems. Interestingly, it has been reported that encapsulation of curcumin in the form of curcuminoid mixture in micelles or nanoparticles retards the degradation of curcumin (18)(19)(20)(21)(22)(23). In this present study, we focused on the curcuminoid mixture because the anticancer and antiinflammatory activities of this mixture were stronger than that of pure curcumin alone and because the curcuminoid mixture has been used in most clinical trials (5,24).…”

Section: Introductionmentioning

confidence: 92%

A Kinetic Degradation Study of Curcumin in Its Free Form and Loaded in Polymeric Micelles

Naksuriya

Steenbergen

Toraño

et al. 2016

AAPS J

View full text Add to dashboard Cite

Abstract. Curcumin, a phenolic compound, possesses many pharmacological activities and is under clinical evaluation to treat different diseases. However, conflicting data about its stability have been reported. In this study, the kinetic degradation of curcumin from a natural curcuminoid mixture under various conditions (pH, temperature, and dielectric constant of the medium) was investigated. Moreover, the degradation of pure curcumin at some selected conditions was also determined. To fully solubilize curcumin and to prevent precipitation of curcumin that occurs when low concentrations of co-solvent are present, a 50:50 (v/v) aqueous buffer/methanol mixture was used as standard medium to study its degradation kinetics. The results showed that degradation of curcumin both as pure compound and present in the curcuminoid mixture followed first order kinetic reaction. It was further shown that an increasing pH, temperature, and dielectric constant of the medium resulted in an increase in the degradation rate. Curcumin showed rapid degradation due to autoxidation in aqueous buffer pH=8.0 with a rate constant of 280×10 -3 h -1, corresponding with a half-life (t 1/2 ) of 2.5 h. Dioxygenated bicyclopentadione was identified as the final degradation product. Importantly, curcumin loaded as curcuminoid mixture in ω-methoxy poly (ethylene glycol)-b-(N-(2-benzoyloxypropyl) methacrylamide) (mPEG-HPMA-Bz) polymeric micelles and in Triton X-100 micelles was about 300-500 times more stable than in aqueous buffer. Therefore, loading of curcumin into polymeric micelles is a promising approach to stabilize this compound and develop formulations suitable for further pharmaceutical and clinical studies.

show abstract

Section: Introductionmentioning

confidence: 92%

A Kinetic Degradation Study of Curcumin in Its Free Form and Loaded in Polymeric Micelles

Naksuriya

Steenbergen

Toraño

et al. 2016

AAPS J

View full text Add to dashboard Cite

show abstract

“…Polymer-drug conjugate strategies are also explored to improve the solubility and stability of curcumin. Solubility of curcumin so far achieved in aqueous medium by conjugation with a polymer is in the range of 852 g/mL (Dey & Sreenivasan, 2014;Kim et al, 2011;Manju & Sreenivasan, 2011).…”

Section: Preparation and Characterization Of Ga-cur Conjugate Micellementioning

confidence: 99%

“…Among the different types of hydrophilic polymers used for conjugation, 3 polysaccharides have gained significant attention because of their biodegradability, biocompatibility, cost effectiveness and presence of large number of reactive functional groups for conjugation and further modification. Sreenivasan and coworkers reported the efficacy of polysaccharides such as hyaluronic acid (HA) and alginate for conjugation of curcumin, considering the hydrophilicity and biodegradability of alginate and HA's affinity towards cell-specific surface markers such as CD44 (Dey & Sreenivasan, 2014;Manju & Sreenivasan, 2011). Both the polymer-curcumin conjugates formed micelle in aqueous medium and showed enhanced toxicity.…”

Section: Introductionmentioning

confidence: 97%

“…Covalent conjugation of curcumin to hydrophilic polysaccharide such as hyaluronic acid and alginate step-up the solubility to 97.5 g/mL and 109 g/mL respectively (Dey & Sreenivasan, 2014;Manju & Sreenivasan, 2011). In the present study, the amount of curcumin conjugated to gum arabic is determined from the standard curve plotted by dissolving curcumin in DMSO-water mixture and measuring the absorption intensity.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Gum arabic-curcumin conjugate micelles with enhanced loading for curcumin delivery to hepatocarcinoma cells

Sarika

James

Kumar

et al. 2015

Carbohydrate Polymers

View full text Add to dashboard Cite

“…To improve stability, water solubility and bioactivity of CUR, a variety of CUR formulations, including nanosuspension (Wei et al, 2013), polymeric nanoparticles (Rejinold et al, 2011) and nanospheres (Arunraj et al, 2014) have been developed. To achieve the enhanced permeability and retention (EPR) effect, CUR has been conjugated with poly(ethylene glycol) (Safavy et al, 2007), oligo(ethylene glycol) (Tang et al, 2010), methoxy-poly(ethylene glycol)-poly(lactic acid) copolymer (Yang et al, 2012) and alignate (Dey & Sreenivasan, 2014) to form micelles. However, it is still a big challenge to overcome the low drug loading (DL%) and low transportation rate of polymeric micelles (Tian & Mao, 2012).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and anti-cancer activity of Pluronic F68–curcumin conjugate micelles

et al. 2015

View full text Add to dashboard Cite

Curcumin (CUR), a nontoxic polyphenol derived from the rhizome of turmeric (Curcuma longa), has been recognized as an anti-cancer and chemo-preventative agent. However, its clinical application for cancer treatment has been greatly limited due to its poor water-solubility and low bioavailability. To tackle this problem, Pluronic F68-CUR (F68-CUR) conjugate micelles, which are amphiphilic copolymers, were designed and synthesized in this study. These highly stable micelles with CUR concentrated in the core were formulated using the solvent evaporation method and were confirmed by Fourier transform infrared spectroscopy and nuclear magnetic resonance. Physicochemical characterization of F68-CUR conjugate micelles revealed that high drug loading content (DL%; 0.248 mg CUR/1 mg F68) was achieved, and the average particle size of micelles was 115.2 ± 3.0 nm. Compared with free CUR, a significantly higher cytotoxicity against human breast cancer cell line MDA-MB-231 was observed in F68-CUR conjugate micelles. The IC value of F68-CUR conjugate micelles was 1.95-fold lower than that of free CUR, indicating that the anti-cancer activity of CUR was significantly improved in the micelles. Furthermore, apoptotic studies demonstrated that F68-CUR conjugate micelles induced more cell apoptosis than that of free CUR. Taken together, these results demonstrate that F68-CUR conjugate micelles are promising to improve the clinical effectiveness of CUR in cancer treatment.

show abstract

Conjugation of curcumin onto alginate enhances aqueous solubility and stability of curcumin

Cited by 146 publications

References 33 publications

A Kinetic Degradation Study of Curcumin in Its Free Form and Loaded in Polymeric Micelles

A Kinetic Degradation Study of Curcumin in Its Free Form and Loaded in Polymeric Micelles

Gum arabic-curcumin conjugate micelles with enhanced loading for curcumin delivery to hepatocarcinoma cells

Synthesis, characterization and anti-cancer activity of Pluronic F68–curcumin conjugate micelles

Contact Info

Product

Resources

About