Polymerizable Vesicles Based on a Single-Tailed Fatty Acid Surfactant: A Simple Route to Robust Nanocontainers

Lee, Jae-Ho; Danino, Dganit; Raghavan, Srinivasa R.

doi:10.1021/la802373j

Cited by 36 publications

(27 citation statements)

References 38 publications

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“…[1] Especially castor oil is a very versatile renewable feedstock for all kinds of polymeric materials, including, e.g., polyesters, polyamides, polyurethanes, and many others. [2] One of the commercially available castor oil derived platform chemicals, 10-undecenoid acid 1, [2,3] was recently used to prepare polyamides X,20, [4] a variety of acyclic diene metathesis derived polyesters, [5][6][7] as well as different cross-linked materials, [8][9][10] thus demonstrating its broad range of application possibilities. Moreover, methyl 10-undecenoate 2 was shown to be a suitable starting material for the preparation of a,v-bisfunctional fatty acids for polycondensation polymers via cross-metathesis with methyl acrylate, [11] acrylonitrile, [12] and allyl chloride.…”

Section: Introductionmentioning

confidence: 99%

Fatty Acid Derived Monomers and Related Polymers Via Thiol‐ene (Click) Additions

Türünç

Meier

2010

Macromol. Rapid Commun.

174

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Thiol‐ene additions of methyl 10‐undecenoate, a castor oil derived renewable platform chemical, were studied with the goal of preparing a set of renewable monomers. Good to excellent yields were obtained for these solvent and initiator free thiol‐ene additions. The resulting monomers were then polymerized using TBD as a catalyst, to linear as well as hyperbranched polyesters that also contain thio‐ether linkages. All thus prepared polymers were fully characterized (NMR, GPC, DSC, and TGA) and the results of these investigations will be discussed within this contribution. The thermal analysis of these polymers revealed melting points in the range from 50 to 71 °C. Moreover, no significant weight loss was observed below 300 °C.magnified image

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Section: Introductionmentioning

confidence: 99%

Fatty Acid Derived Monomers and Related Polymers Via Thiol‐ene (Click) Additions

Türünç

Meier

2010

Macromol. Rapid Commun.

174

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“…Due to increasing water content in the sedimented liquid phase, the volume ratio at pH 4.50 was smaller than that at pH 4.00. Huang et al found that surfactants can form vesicles in the ethanol-water-mixed solvents (Huang, Zhu, Zhao, & Zhang, 1997 (Lee, Danino, & Raghavan, 2009). Based on these reports, it is considered that the water content of the sedimented liquid phase increased because Zonyl FSA forms vesicles at pH values close to the pKa.…”

Section: Holle Of Rhmentioning

confidence: 99%

Powerful Concentration of Rhodium in Plating Wastewater Using Homogeneous Liquid–Liquid Extraction (HoLLE) and Study for Scale-up

Kato¹,

Saito²,

Oshite³

et al. 2017

ENRR

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A powerful technique for the concentration of rhodium (Rh) in plating wastewater was developed. The technique entails complexing Rh with 1-(2-pyridylazo)-2-naphthol (PAN) followed by homogeneous liquid-liquid extraction (HoLLE) with Zonyl FSA. The optimum HoLLE conditions were determined as follows: [ethanol] T = 30.0 vol.%, pH = 4.00, and Rh:PAN = 1:5. Under these optimum conditions, 88.1% of Rh was extracted into the sedimented liquid phase. After phase separation, the volume ratio [aqueous phase (Va) /sedimented liquid phase (Vs)] of Va and Vs was 1000 (50 mL → 0.050 mL). We then applied the new method to wastewater generated by the plating industry. The phase separation was satisfactorily achieved when the volume was scaled up to 1000 mL of the actual wastewater; 84.7% of Rh was extracted into the sedimented liquid phase. After phase separation, Va/Vs was 588 (1000 mL → 1.70 mL).

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“…Undecylenic acid vesicles with diameters in the 20 nm to 100 nm range has been reported. [1] However, these vesicles have not yet been characterized as drug delivery systems. The aim of the current research is to characterize undecylenic acid vesicles as potential carriers for targeted drug delivery systems.…”

Section: Extended Abstractmentioning

confidence: 99%

Comparison of Micellar and Vesicle-Based Drug Delivery Systems

Amato¹,

Larrabee²

2017

Proceedings of the 2nd World Congress on New Technologies

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Extended AbstractTargeted drug delivery systems deliver therapeutic agents to specific locations in the body where they can act on the diseased tissue. An effective carrier will bind the drug and remain stable while circulating in the bloodstream until it reaches the diseased site where it will release the drug. Carriers with a diameter on the order of 10 to 200 nanometers accumulate in cancerous tumors due to the enhanced permeability and retention (epr) effect. The rapid growth of tumor cells causes leakiness in the adjacent vasculature allowing small particles to pass through. Since lymphatic drainage in the tumor cells is limited, drug-loaded carriers will passively build up in the cancerous tissue. A general problem with epr is tailoring the size of the carriers to the size of the crevices in the vasculature. Undecylenic acid vesicles with diameters in the 20 nm to 100 nm range has been reported.[1] However, these vesicles have not yet been characterized as drug delivery systems. The aim of the current research is to characterize undecylenic acid vesicles as potential carriers for targeted drug delivery systems. Previous studies of micellar drug delivery model systems based on undecylenic acid have shown that while they are less than 5 nm in diameter [2], they are capable of binding [3] and protecting [4] hydrophobic substrate in aqueous solution at physiological pH (7.4) and releasing the substrate at tumor pH (< 7) [5]. If these features can be maintained in the vesicles while increasing the diameter to more than 20 nm, all of the components for a therapeutic drug delivery system will be in place. Further, the aqueous interior of the vesicles opens up the possible of multifunctional carriers providing simultaneous delivery of both hydrophobic and hydrophilic drugs to the targeted sites.Here we report on the solubilization of two hydrophobic substrates by unpolymerized and polymerized sodium 10-undecenoate (NaU) vesicles and compare the results to the micellar systems [6]. Solubilization power (SP) was determined for Oil Blue N by visible light absorbance at 600nm. The results, in mmol (substrate)/mol (NaU), are 1.48 ± 0.21(unpolymerized) and 0.68 ± 0.37 (polymerized). Both values are approximately four times the corresponding values for the micellar systems, 0.37 ± 0.04 and 0.14 ± 0.01. The relative polarity [7] of the environment at the substrate binding site was determined for the solvatotropic probe, Nile Red, by fluorescence spectroscopy. Polymerization of the micelle produced a large change in relative polarity, from 0.58 ± 0.02 to 0.80 ± 0.02. Polymerization of the vesicle produced a much smaller effect, from 0.69 ± 0.02 to 0.75 ± 0.02.The overall results encourage further study of the sodium 10-undecenoate vesicle system for the rational design of therapeutic drug delivery systems. The transition from micelles to vesicles increases the solubilization power fourfold which would produce more efficient delivery. Further, the lack of sensitivity of the polarity of the binding site to polymerization giv...

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Polymerizable Vesicles Based on a Single-Tailed Fatty Acid Surfactant: A Simple Route to Robust Nanocontainers

Cited by 36 publications

References 38 publications

Fatty Acid Derived Monomers and Related Polymers Via Thiol‐ene (Click) Additions

Fatty Acid Derived Monomers and Related Polymers Via Thiol‐ene (Click) Additions

Powerful Concentration of Rhodium in Plating Wastewater Using Homogeneous Liquid–Liquid Extraction (HoLLE) and Study for Scale-up

Comparison of Micellar and Vesicle-Based Drug Delivery Systems

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