20, 21 Servat et al (1990) reported the biological synthesis of amphiphilic molecule-fatty hydroxamic acids using the Mucor miehei lipase by reacting hydroxylamine with fatty acids in their free or methyl ester form. 16– 19 Enzymes have also been used as catalysts for the synthesis of hydroxamic acids.
6– 15 Hydroxamic acids can be synthesized using different methods and most of them consist of multistep reactions that are time-consuming and costly due to the use of expensive raw materials. Several biological and chemical applications for hydroxamic acids and their derivatives have been reported, such as metal extraction chelators, cell-division factors, food additives, growth factors, antimicrobial agents, antimalarial drugs, tumor inhibitor drugs and enzyme inhibitors. Hydroxamic acids and their derivatives are weak organic acids with low toxicity, which have been widely studied for over half of a century. 4, 5 In the current work, castor oil was used as a raw material for the synthesis of nano ricinoleyl hydroxamic acid (RHA). 1– 3 It has been used in several applications, such as the production of biodiesels, biomass, antioxidants and drugs. Ricinoleic acid is a poly-unsaturated fatty acid and its high concentration in castor seeds might be responsible for castor oil’s remarkable properties. Castor oil is a triglyceride of fatty acids and almost 90% of them consist of ricinoleic acid. From a historical point of view, castor oil has been used for lubricating leather goods, as fuel for lamps and as a Galenic medicine for some diseases. Keywords: ricinoleyl hydroxamic acid, enzymatic reaction, anticancer agent, biomedicine, lipozyme and castor oilĬastor oil is extracted from castor seeds that are native plants of India. Results: RHA was successfully synthesized and it demonstrated strong anticancer activity against glioblastoma and melanoma cells at as low as a 1 μg/mL concentration while it did not demonstrate any toxicity against HDF cells.Ĭonclusion: This is the first report on the synthesis of RHA with great potential to be used as a new anticancer agent. The cytotoxicity of the synthesized RHA was assessed using human dermal fibroblasts (HDF), and its application towards fighting cancer was assessed using melanoma and glioblastoma cancer cells over a duration of 24 and 48 hours. The highest conversion was obtained when the reaction was carried out under the following conditions: hexane as a solvent reaction period of 48 hours 120 mg of Lipozyme TL IM/3 mmol oil HA-oil ratio of 19 mmol HA/3 mmol oil and temperature of 40☌. To optimize the conversion, the effects of the following parameters were investigated: type of organic solvent, period of reaction, amount of enzyme, the molar ratio of reactants and temperature. Methods: Ricinoleyl hydroxamic acid (RHA) was synthesized from castor oil and hydroxylamine using Lipozyme TL IM as a catalyst. Hossein Jahangirian, 1 Bahram Saleh, 1 Katayoon Kalantari, 1 Roshanak Rafiee-Moghaddam, 1 Bahareh Nikpey, 2 Siavash Jahangirian, 3 Thomas J Webster 1ġDepartment of Chemical Engineering, College of Engineering, Northeastern University, Boston, MA 02115, USA 2Department of Agronomy and Plant Breeding, Faculty of Engineering and Agriculture, Science and Research Branch, IA University, Tehran, Iran 3Department of Agronomy, Faculty of Agriculture, IA University, Tehran, IranĬorrespondence: Hossein Jahangirian Thomas J Webster Email īackground: New anticancer agents that rely on natural/healthy, not synthetic/toxic, components are very much needed.
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