Abstract
A sensitive and accurate high performance liquid chromatography with ultraviolet/visible light detection (HPLC-UV/VIS) method for the quantification of 2,6-bis-(4-hydroxy-3-methoxybenzylidene)-cyclohexanone (BHMC) in rat plasma was developed and validated. BHMC and the internal standard, harmaline, were extracted from plasma samples by a simple liquid–liquid extraction using 95% ethyl acetate and 5% methanol. Plasma concentration of BHMC and internal standard were analyzed by reversed phase chromatography using a C18 column (150 × 4.6 mm I.D., particle size 5 µm) and elution with a gradient mobile phase of water and methanol at a flow rate of 1.0 mL/min. Detection of BHMC and internal standard was done at a wavelength of 380 nm. The limit of quantification was 0.02 µg/mL. The calibration curves was linear (R2 > 0.999) over the concentration range of 0.02–2.5 µg/mL. Intra- and inter-day precision were less than 2% coefficient of variation. The validated method was then applied to a pharmacokinetic study in rats by intravenous administration of BHMC at a single dose of 10 mg/kg. Pharmacokinetic parameters such as half-life, maximum plasma concentration, volume of distribution, clearance and elimination rate constant for BHMC were calculated.
Highlights
Curcumin [1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, Figure 1a] has been shown to modulate several chronic diseases at both pre-clinical and clinical stages of experimentation [1]. the clinical applicability of curcumin is limited by its low bioavailability via oral administration [2,3,4,5]
The clinical applicability of curcumin is limited by its low bioavailability via oral administration [2,3,4,5]
The method developed was rapid, as the internal standard (IS) peak and BHMC peak could be detected at 6.97 ± 0.134 and 13.20 ± 0.080 min, respectively
Summary
Curcumin [1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, Figure 1a] has been shown to modulate several chronic diseases at both pre-clinical and clinical stages of experimentation [1]. the clinical applicability of curcumin is limited by its low bioavailability via oral administration [2,3,4,5]. Several approaches have been adopted to enhance the bioavailability of curcumin while retaining its therapeutic potential. Such approaches range from the use of liposomal formulations [6], production of nanoparticles [7], and inhibition of metabolic enzymes [8] to the design of synthetic structural derivatives [9,10]. BHMC [2,6-bis-(4-hydroxy-3-methoxybenzylidene)-cyclohexanone, Figure 1b] is a synthetic curcuminoid analogue that was synthesized in an attempt to enhance the bioavailability of curcumin while retaining its therapeutic effects [11]. BHMC retains curcumin’s phenolic OH functional group that is responsible for its antioxidant properties, while the β-diketone moiety that makes curcumin be rapidly metabolized was replaced by a relatively stable cyclohexanone structure [11,12]
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