Conjugation of curcumin onto hyaluronic acid enhances its aqueous solubility and stability

• Published in: Journal of colloid and interface science Vol. 359; no. 1; pp. 318 - 325
• Main Authors: Manju, S., Sreenivasan, K.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Inc 01.07.2011; Elsevier
• Subjects: Animals; bioavailability; Cells, Cultured; Chemistry; Colloidal state and disperse state; Conjugates; Conjugation; Curcumin; Curcumin - chemistry; Curcumin - pharmacology; Cytotoxicity; Degradation; Drug Stability; Drugs; Effectiveness; Esterification; Exact sciences and technology; Fibroblasts; Fibroblasts - cytology; Fibroblasts - drug effects; Fourier transform infrared spectroscopy; General and physical chemistry; Hyaluronic acid; Hyaluronic Acid - chemistry; Hyaluronic Acid - pharmacology; Hydrogen-Ion Concentration; light scattering; medicinal properties; Mice; Micelles; Micelles. Thin films; Molecular Structure; MTT assay; nuclear magnetic resonance spectroscopy; Particle Size; Polymer conjugates; Solubility; Stability; Structure-Activity Relationship; Surface Properties; transmission electron microscopy; Water - chemistry; water solubility; Degradation; Stability; Polymer conjugates; Micelles; Solubility; Cytotoxicity; Curcumin; Hyaluronic acid; MTT assay; Esterification; Drug; Light scattering; Micelle; Polymer; NMR spectrometry; Assay; Infrared spectrometry; Transmission electron microscopy; Dynamics; Water solubility; pH
• ISSN: 0021-9797; 1095-7103
• DOI: 10.1016/j.jcis.2011.03.071

We tried a simple method for the direct conjugation of curcumin to hyaluronic acid by utilizing reactive functional groups in hyaluronic acid such as carboxylic acid. Hyaluronic acid–curcumin conjugates form nano sized micelle in aqueous solution through hydrophobic interactions which enhances poor aqueous solubility and stability of curcumin. [Display omitted] ► Polymer-drug conjugates have gained much attention largely to circumvent lower drug solubility and to enhance drug stability. ► Curcumin is widely known for its medicinal properties including its anticancer efficacy. One of the serious drawbacks of curcumin is its poor water solubility which leads to reduced bioavailability. ► We synthesized Hyaluronic acid–curcumin (HA–Cur) conjugate. ► The conjugates, interestingly found to assembles as micelles in aqueous phase. ► The formation of micelles seems to improve the stability of the drug in physiological pH. Polymer-drug conjugates have gained much attention largely to circumvent lower drug solubility and to enhance drug stability. Curcumin is widely known for its medicinal properties including its anticancer efficacy. One of the serious drawbacks of curcumin is its poor water solubility which leads to reduced bioavailability. With a view to address these issues, we synthesized hyaluronic acid–curcumin (HA–Cur) conjugate. The drug conjugate was characterized using FT-IR, NMR, Dynamic light scattering and TEM techniques. The conjugates, interestingly found to assembles as micelles in aqueous phase. The formation of micelles seems to improve the stability of the drug in phisiological pH. We also assessed cytotoxicty of the conjugate using L929 fibroblast cells and quantified by MTT assay.