Lipase catalyzed synthesis of ester‐based surfactants from biomass derivatives

Karmee, Sanjib Kumar

doi:10.1002/bbb.60

Cited by 52 publications

(21 citation statements)

References 85 publications

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“…It is also well established that blood-brain barrier cells express high levels of the glucose transporter GLUT1 (Pardridge, 1995), therefore, sugar-based niosomal drug delivery systems could be a valuable approach for achieving an efficient targeted drug delivery to the brain (Bragagni et al, 2014). Therefore, glycosidic surfactant systems are gifted candidates for replacing the traditional surfactants used for pharmaceutical and cosmetic preparations (Karmee, 2008;Muzzalupo et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Sugar-based novel niosomal nanocarrier system for enhanced oral bioavailability of levofloxacin

et al. 2016

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Context: Vesicular systems have attracted great attention in drug delivery because of their amphiphilicity, biodegradability, non-toxicity and potential for increasing drug bioavailability. Objective: A novel sugar-based double-tailed surfactant containing renewable block was synthesized for preparing niosomal vesicles that could be exploited for Levofloxacin encapsulation, aiming to increase its oral bioavailability. Materials and methods: The surfactant was characterized by 1 H NMR, mass spectroscopy and Fourier transform infrared spectroscopy (FT-IR). Its biocompatibility was studied against cell cultures and human blood hemolysis. In vivo acute toxicity was evaluated in mice. The vesicle morphology, size, drug-excipients interaction and entrapment efficiency (EE) were examined using atomic force microscope (AFM), dynamic light scattering (DLS), FT-IR and HPLC. Oral bioavailability studies of Levofloxacin in surfactant-based niosomal formulation were carried out using rabbits and plasma samples were analyzed using HPLC. Results and discussion: Vesicles were spherical in shape and the size was 190.31 ± 4.51 nm with a polydispersity index (PDI) of 0.29 ± 0.03. The drug EE in niosomes was 68.28 ± 3.45%. When applied on cell lines, high cell viability was observed even after prolonged exposure at high concentrations. It caused 5.77 ± 1.34% hemolysis at 1000 mg/mL and was found to be safe up to 2000 mg/kg. Elevated Levofloxacin plasma concentration was achieved when delivered with novel vesicles. Conclusion:The surfactant was demonstrated to be safe and effective as carrier of Levofloxacin. The study suggests that this sugar-based double-tailed nonionic surfactant could be promising nano-vesicular system for delivery and enhancing oral bioavailability of the hydrophobic Levofloxacin.

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Section: Introductionmentioning

confidence: 99%

Sugar-based novel niosomal nanocarrier system for enhanced oral bioavailability of levofloxacin

et al. 2016

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“…For example, enzymatic synthesis can be completed in mild conditions, and it is easy to purify the product and remove its color. In addition, lipase itself is considered highly regioselective [4][5][6][7]. Substances with optical activity can be synthesized via enzymatic synthesis [8,9].…”

Section: Introductionmentioning

confidence: 99%

Study of ultrasound-promoted, lipase-catalyzed synthesis of fructose ester

Zhu

Liu

Han

et al. 2010

Front. Chem. Eng. China

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The effect of low energy ultrasound in biochemistry and biotechnology has attracted great attention in recent years. It can enhance substrate dissolution and improve mass transfer within and outside of a cell, both of which are beneficial to the synthesis of fructose ester. Here we describe the experimental study of the effect of ultrasounds of different intensity on the lipase-catalyzed synthesis of fructose ester in the solvent butanone. The results were compared with control reactions performed with no ultrasound. High performance liquid chromatography (HPLC) and thin layer chromatography (TLC) were used for qualitative and quantitative analyses. The results show the following: 1) the concentration of monoester and diester increased with the reaction time, either with or without ultrasonic irradiation. Low energy ultrasound accelerated the reaction due to the effect of ultrasonic steady cavitations, and high energy ultrasound was not beneficial to the reaction. 2) The application of ultrasound played an important role in our lipase-catalyzed reaction. It decreased reaction time as compared to a reaction without ultrasound that resulted in the same yield, increased reaction rate, and enhanced the amount of fructose ester produced. When the frequency was 10 kHz and sound intensity was 0.16 W%m -2 , the concentration of ester was twofold more than without ultrasonic irradiation after a reaction time of up to 12 h. With the proper ultrasonic parameters, the overall concentration of production appeared to increase exponentially with the reaction time. 3) Ultrasound had little effect on the initial reaction rate, and continuous ultrasonic irradiation was favorable for the reaction. The longer the reaction continued, the more obvious the effects of the ultrasound became in our experiments.

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“…Lipases, sn-1, 3 specific and non-specific have been reported in literature for the esterification reaction giving varied degree of conversion and diverse products [26]. In the present study Novozym 435 lipase which is non-specific was evaluated for synthesis of glyceryl monostearate.…”

Section: Effect Of Molar Ratio Of Substratesmentioning

confidence: 99%

Production of Glyceryl Monostearate by Immobilized Candida Antarctica B Lipase in Organic Media

Odaneth¹

2017

JABB

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Chemical methods of synthesizing monoglycerides (MGs) produce mixture of acylglycerols making the synthesis of MGs of a single fatty acid type not possible through this route. Lipases due to their selectivity and specificity offer a useful way of synthesizing highly purified single fatty acid containing monoglycerides. Glyceryl monostearate (GMS), a nonionic amphiphilic monoglyceride of glycerol and stearic acid is widely used as emulsifier in food, cosmetic, pharmaceutical and textile industry. In the present work, lipase mediated synthesis of GMS was explored using Novozym 435 and indigenously immobilized Candida antarctica B lipase. Direct esterification of glycerol and stearic acid was used as strategy and various parameters that influence synthesis of glyceryl monostearate such as molar ratio of substrates, enzyme load, reaction time and solvent polarity were systematically studied using Novozym 435 lipase. Esterification efficiency of indigenously immobilized Candida antarctica B lipase and Novozym 435 was compared for synthesis of GMS and indigenously immobilized Candida antarctica B lipase gave conversion competitive to Novozym 435. Indigenously immobilized Candida antarctica B lipase in the presence of homogenous substrate solution using tert-butyl alcohol as the reaction medium, resulted in exclusive production of monoglyceride without formation of diglyceride. Continuous production of GMS was also carried out in packed bed reactor and 94% conversion of stearic acid was achieved.

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Lipase catalyzed synthesis of ester‐based surfactants from biomass derivatives

Cited by 52 publications

References 85 publications

Sugar-based novel niosomal nanocarrier system for enhanced oral bioavailability of levofloxacin

Sugar-based novel niosomal nanocarrier system for enhanced oral bioavailability of levofloxacin

Study of ultrasound-promoted, lipase-catalyzed synthesis of fructose ester

Production of Glyceryl Monostearate by Immobilized Candida Antarctica B Lipase in Organic Media

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