• Applied Chemistry for Engineering
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• v.16 no.6
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• pp.834-841
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• 2005

Polyethylene glycol esters (PEG-esters) were synthesized by condensation reaction of dicarboxylic acid such as adipic acid and sebacic acid and several PEGs. The PEG-esters were analyzed by FT-IR, $^1H-NMR$ and HPLC for structure analysis, and by GPC for molecular weight. Through the analysis of surface tension, critical micelle concentration (CMC), aluminum contact angle of water solution containing the PEG-ester, the synthetic PEG-esters are proven to exhibit surfactant properties. The surface tension ranged from 45 to 50 dyn/cm depended on the concentration and structures of the PEG-esters. The surface tension of PEG-esters with sebacic acid moiety and short polyoxyethylene unit resulted in lower value than that of PEG-ester with adipic acid moiety and long polyoxyethylene unit. The CMC of water solution containing 2.5 wt% PEG-ester with sebacic acid moiety estimated at $0.9{\times}10^{-5}{\sim}5.3{\times}10^{-3}mol/L$ depended on the structures of PEG-esters. The CMC of PEG-esters with long polyoxyethlene unit showed a higher value than that of PEG-esters with short polyoxyethylene unit. Meanwhile, the CMC of PEG-esters with adipic acid moiety was not distinct due to their high hydrophilic character. As the results of contact angle and cutting time aginst aluminum, the contact angle ranged from $45^{\circ}$ to $53^{\circ}$ depended on the concentration of PEG-esters. The cutting time of aluminum showed the shortest value at CMC, but the longest value above CMC. This fact indicates that the CMC of PEG-esters is a very important factor in drilling aluminum.

• YAKHAK HOEJI
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• v.29 no.5
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• pp.234-245
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• 1985

To clarify the diffusional behavior of p-aminbenzoic acid esters in the presence of polyethylene glycol 400, cellulose membrane permeation rate, solubility and viscosity of p-aminobenzoic acid methyl ester, benzocaine and butamben were determined with PEG solutions of various concentrations. With an increase in PEG concentrations permeation rates from solutions; decreased due to an increase in viscosity of the solution. From suspensions, however, permeation rates increased due to an increase in solubility and when the initial drug concentration was constant, permeation rates were found to be greatest from the PEG-water system with the PEG concentration which transported from the solution to the suspension. Permeation rate of 4.0mg/ml p-aminobenzoic acid methyl ester was $26.51\mu$g/ml$\cdot$hr from 5g/100ml PEG solution, and that of 4.0mg/ml benzocaine was $13.17{\mu}g/ml{\cdot}hr$ from 15g/100ml PEG, solution, and that of 2.0mg/ml butamben was $3.8{\mu}g/ml{\cdot}hr$ from 10g/100ml PEG solution. Permeation rate was 7.0 fold in p-aminobenzoic acid methyl, ester and 3.5 fold in benzocaine compared to butamben.

• Archives of Pharmacal Research
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• v.27 no.8
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• pp.878-883
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• 2004

Tacrolimus (FK506), which is isolated from Streptomyces tsukubaensis, is a new potent immu-nosuppressant. Because of poor solubility in water, the conventional intravenous dosage forms of tacrolimus contain surfactants such as cremophor EL (BASF Wyandotte Co.) or hydroge-nated polyoxy 60 castor oil (HCO-60) which may cause adverse effects. This study relates to a polymer-tacrolimus conjugate, which can be dissolved in water, formed by chemically binding the sparingly soluble drug, tacrolimus, with the water soluble polymer, methoxypoly(ethylene glycol) (mPEG). Water soluble tacrolimus-mPEG conjugates have been synthesized and shown to be function in vitro as prodrugs. These conjugates are in the form of an ester wherein the 24-, 32- or 24,32-positions are esterified. The desired 24-, 32- or 24,32-esterified com-pounds were obtained by initially acylating of tacrolimus with iodoacetic acid at the 24-,32-, or 24,32-positions and then reacting the resulting acylated tacrolimus with a mPEG in the pres-ence of a base such as sodium bicarbonate. These conjugates were converted again into tac-rolimus by the action of enzymes in human liver homogenate, and the half-lives of the conjugates are approximately 10 min in the homogenate, indicating that the esterified tacroli-mus derivatives may be practically applicable as a prod rug for the immunosuppressant.

• Biomolecules & Therapeutics
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• v.19 no.1
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• pp.109-117
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• 2011

In this work, we have investigated the effect of polyoxyethylene alkyl ester nonionic surfactants on percutaneous permeation enhancement of a model drug, ketoprofen. We also investigated the mechanism involved in the enhancement using impedance and solubility measurement. Three groups of nonionic surfactants with different ethylene oxide content were studied. The permeation results showed that all surfactants enhanced the percutaneous absorption, irrespective of the molecular weight. The permeation results from PEG-45 monostearate (PEGMS45) were rather unexpected. Impedance and solubility results indicate that the mechanism involved in the enhancement of permeation by PEG-10 monooleate (PEGMO10) and PEGMS45 is rather different. The results from PEGMS45 suggest that it could be a potential candidate as a skin penetration enhancer with high molecular weight, which may poses less skin irritation and systemic side effect than the smaller surfactant molecules. Overall, this work provided some useful information on percutaneous transport enhancement and the mechanistic insights involved in skin permeation for these nonionic surfactants.

• Macromolecular Research
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• v.15 no.5
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• pp.437-442
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• 2007

Poly(ethylene glycol) methyl ether (PEG)-poly(${\beta}$-amino ester) (PAE) block copolymers were synthesized using a Michael-type step polymerization, and the construction of pH-sensitive polymeric micelles (PM) investigated. The ${\beta}$-amino ester block of the block copolymers functioned as a pH-sensitive moiety as well as a hydrophobic block in relation to the ionization of PAE, while PEG acted as a hydrophilic block, regardless of ionization. The synthesized polymers were characterized using $^1H-NMR$, with their molecular weights measured using gel permeation chromatography. The $pK_b$ values of the pH-sensitive polymers were measured using a titration method. The pH-sensitivity and critical micelle concentration (CMC) of the block copolymers in PBS solution were estimated using fluorescence spectroscopy. The pH dependent micellization behaviors with various bisacrylate esters varied within a narrow pH range. The critical micelle concentration at pH 7.4 decreased from 0.032 to 0.004 mg/mL on increasing the number of methyl group in the bisacrylate from 4 to 10. Also, the particle size of the block copolymer micelles was determined using dynamic light scattering (DLS). The DLS results revealed the micelles had an average size below 100 nm. These pH-sensitive polymeric micelles may be good carriers for the delivery of an anticancer drug.

• Bulletin of the Korean Chemical Society
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• v.26 no.7
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• pp.1079-1082
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• 2005

The purpose of this study was to develop a method for increasing the solubility of paclitaxel in water to reduce its toxicity and make the drug more feasible for chemotherapy. A series of highly water soluble paclitaxel polyethylene glycol (PEG) esters were synthesized and evaluated for their anti-tumor activity and toxicity. The solubility of 7-polyethylene glycol paclitaxel carbonate 5 was 840 mg/mL and the acute toxicity ($LD_{50}$) was 286 mg/kg. Because of its reduced toxicity, compound 5 showed a dramatic reduction of tumor volume without any loss of animals in long-term treatment (daily consecutive injections for 15 days).

• Journal of the Society of Cosmetic Scientists of Korea
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• v.30 no.3 s.47
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• pp.369-375
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• 2004

In this study, liquid crystalline (LC) is formed using Gemini surfactant (GS) type and moisturizing effect in vivo is measured. $3.0\;wt\%$ of sodium dicocoyl ethylene diamine (PEG)-15 sulfate (SCD-PEG-15S) is used as GS and $4.0\;wt\%$ of hydrogenated dimer acid esters (HDAE) as booster. For stabilizers, $2.0\;wt\%$ of behenyl alcohol (BA) and $1.0\;wt\%$ of Iyso-lecithin (LyL) are utilized. It is stabilized in pH from 4.0 to 10.5 and the best condition is in pH 6.5. The value of viscosity is $8,000\pm500$ cP. The most excellent particles are formed within the range of 4.0 to 15.5 um. Formed LC is observed around LC particles using polarization microscope. It is also observed that lamellar gel network structure is formed around LC particles. Moisturizing effect is improved by $13.6\%$ (P<0.05) compared to control when measured 30 min later after coating samples. After 1 h, moisturizing effect is improved by 1$12.6\%$ (P<0.05) than control while showing $28.3\%$ (P<0.05) of improvement after 4 h. These results may be caused from that manufactured LC forms lamellar structure so that it has better water-holding ability and absorbance of oil increases. This formula could be utilized by delivery system (DS) on skin so that this technology can be applied for manufactuing pharmaceuticals and cosmetics.

• Journal of the Korean Applied Science and Technology
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• v.36 no.4
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• pp.1443-1459
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• 2019

Polyglycerol fatty acid ester nonionic surfactants have been used for a long time in foods and have been suggested as an alternative to the safety problems of PEG based nonionic surfactants. The polyglycerol fatty acid ester surfactants are synthesized by combining a hydrophilic polyglycerin and a lipophilic fatty acid. The hydrophilic polyglycerin is polymerized using glycerin, glycidol, epichlorohydrin, etc. The main issues of the polyglycerol polymerization reaction are to increase the content of the polyglycerol in the form of linear rather than branched or cyclic forms and to narrow the distribution of the degree of polymerization. The method of binding a lipophilic fatty acid group to a hydrophilic polyglycerin includes chemical synthesis such as esterification reaction and enzyme synthesis using lipase enzyme. The main issues of polyglycerin fatty acid ester synthesis are to increase the yield and to control the degree of esterification while reducing side reactions.