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Keto–Enol Tautomerism of Temperature and pH Sensitive Hydrated Curcumin Nanoparticles: Their Role as Nanoreactors and Compatibility with Blood Cells

Kaur, Rajpreet, Khullar, Poonam, Mahal, Aabroo, Gupta, Anita, Singh, Narpinder, Ahluwalia, Gurinder Kaur, Bakshi, Mandeep Singh
Journal of agricultural and food chemistry 2018 v.66 no.45 pp. 11974-11980
bioavailability, biocompatibility, blood cells, color, curcumin, dose response, enols, gold, hydrogen bonding, nanoparticles, pH, palladium, silver, tautomerization, temperature, water solubility
In order to provide a solution for the poor aqueous solubility and poor bioavailability of curcumin, we present the synthesis and characteristic features of water-soluble curcumin hydrated nanoparticles (CNPs). They are stable and nearly monodisperse in the aqueous phase where the keto form of curcumin self-assembles into spherical CNPs, which are highly sensitive to temperature and pH variations. The CNPs are quite stable up to 40 °C and at neutral pH. A higher temperature range reduces their hydration and makes them unstable, thereby disintegrating them into smaller aggregates. Similarly, a higher pH converts the keto form of CNPs into the enol form by promoting their interparticle fusions driven by hydrogen bonding with a remarkable color change from yellow to bright orange-red which demonstrates their excellent photophysical behavior. The stable keto form CNPs are highly efficient nonreactors for the in situ synthesis of Au, Ag, and Pd NPs which are simultaneously entrapped in curcumin aggregates, thus promoting the metal NP carrying ability of curcumin aggregates. The CNPs also demonstrate their excellent dose-dependent biocompatibility with blood cells. A concentration range up to 5 mM of CNPs is quite safe for their applications in biological systems.