Synthesis and characterization of some novel fatty acid analogues: A preliminary investigation on their activity against
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RESEARCH
Open Access
Synthesis and characterization of some novel fatty acid analogues: A preliminary investigation on their activity against human lung carcinoma cell line Selvaraj Jubie1*, Palanisamy Dhanabal2, Mohammed Afzal Azam1, Nithyanantham Muruganantham2, Rajagopal Kalirajan1 and Kannan Elango2
Abstract Background: Preparation of some novel heterocyclic compounds with long alkyl and alkenyl chain of cytotoxic activity. Methods: Gamma linolenic acid, a poly unsaturated fatty acid and stearic acid, a saturated fatty acid were isolated from the microalga Spirulina platensis. Some novel gamma linolenic acid and stearic acid analogues having 1,3, 4-oxadiazole and 1,2,4-triazole were synthesized and characterized by IR, 1H NMR, 13C NMR and mass spectral analysis. Cytotoxicity of these compounds was evaluated by the growth inhibition of A-549 cells in-vitro. Results: Compound 1 and 3 showed comparable cytotoxicity against the human lung carcinoma A-549 cell lines. Keywords: Spirulina platensis, Stearic acid, Gamma linolenic acid, Cytotoxicity
Background Spirulina platensis, blue green microalgae is being widely studied, not only for nutritional reasons but also for its reported medicinal properties [1]. It is a potential source of GLA (Gamma linolenic acid), an essential polyunsaturated fatty acid of excellent economic interest [2]. In-vitro and in-vivo studies have shown GLA to selectively kill tumor cells without harming normal cells [3]. Natural sources of GLA contain variable amounts of this acid which rarely exceed 25%; hence there has been a keen interest in producing higher concentrates of GLA. The commercial methods for producing GLA concentrates include winterization, fractional distillation, urea-inclusion, high performance liquid chromatography and argentated silica gel chromatography [4]. GLA concentrations mentioned above are sufficient for most applications; however several uses, particularly pharmaceutical applications require higher concentrations of * Correspondence: [email protected] 1 Department of Pharmaceutical Chemistry, JSS College of Pharmacy, Udhagamandalam, Rock lands, Ooty 643 001 Tamilnadu, India Full list of author information is available at the end of the article
GLA, often in excess of 90% [5]. Recently Centrifugal chromatography system was shown to play a vital role in extracting phyto constituents from natural sources. Although billions of dollars have been spent on research and development on anticancer drugs, the disease remains uncontrolled. A number of investigations have demonstrated that, a variety of modified fatty acid analogues are promising molecules in cancer prevention and have potential in the treatment of cancer [6,7]. During the last two decades, the chemistry of 1,2,4-triazole, 1,3,4-oxadiazole and their derivatives have received considerable attention owing to their anticancer activities [8-10]. Based on these findings and continuation of our previous work [11], the present work has been aimed to develop some novel 1,2,4-triazoles and 1,3,4 oxadiazoles
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