Synthesis and characterization of cinnamic acid based glyceride and its application for developing self-nanoemulsifying drug delivery system for curcumin oral delivery

Curcumin (CU) possesses diverse pharmacological activities while being relatively safe; nevertheless, its clinical application is limited due to its physico-chemical characteristics. This study aimed to synthesize cinnamic acid based glyceride for use in a self-nanoemulsifying drug delivery system (SNEDDS) to enhance CU anticancer activity and oral bioavailability. The synthesized glyceride was characterized by ESI-mass spectrometry, ¹H-NMR spectroscopy, and ¹³C-NMR spectroscopy. The potential of synthesized glyceride as an oil component in SNEDDS was explored in combination with surfactant and co-surfactant. The concentration of SNEDDS components was optimized through a ternary phase diagram. The composition of 40% surfactant, 10% co-surfactant, and 50% synthetic glyceride as oil was selected as the optimized formulation.

Highlights

• Cinnamic acid based glycerideshave successfully synthesized

• DCG was used as an oil phase in the development of SNEDDS

• Synthesized glyceride (DCG) was capable to dissolve 12.5 mg Curcumin

• The DCG based SNEDDS was highly stable with the nano range droplets

• The developed SNEDDS showed enhanced in-vitro Anticancer activity of curcumin

• DCG based SNEDDS significantly enhance the oral bioavailability of curcumin

The optimized formulation was characterized through Zeta sizer, atomic force microscope (AFM) and FTIR, and was then evaluated for dilution and thermodynamic stability. The CU-loaded SNEDDS revealed nano-size droplets (182.06 ±6.90 nm) with -20.96 ± 0.61 mV surface negativity. The optimized SNEDDS was highly stable and maintained the chemical nature of the drug. The anticancer activity of CU was enhanced upon encapsulation in novel SNEDDS. Similarly, the CU bioavailability improved significantly upon oral administration in novel SNEDDS. It can be safely concluded that the novel synthetic glyceride based SNEDDS can significantly improve CU bioavailability and anticancer activity.

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Muhammad Abdullah, Tasmina Kanwal, Ali Asgher Shuja, Komal Rao, Khadija Rehman, Muhammad Kawish, Shabana Usman Simjee, Sirajuddin, Muhammad Raza Shah,
Synthesis and characterization of cinnamic acid based glyceride and its application for developing self-nanoemulsifying drug delivery system for curcumin oral delivery,
Journal of Molecular Structure, Volume 1263, 2022, 133131, ISSN 0022-2860,
https://doi.org/10.1016/j.molstruc.2022.133131.