Membrane matrix for the hydrolysis of amino acid esters with marked enantioselectivity

Ueoka, Ryuichi; Matsumoto, Yōko; Moss, Robert A.; Swarup, Shanti; Sugii, Atsushi; Harada, Kumiko; Kikuchi, Jun‐ichi; Murakami, Yukito

doi:10.1021/ja00213a035

Cited by 155 publications

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“…The physical properties of these liposomes such as size, membrane fluidity, phase transition temperature, and hydrophobicity can be controlled by changing the constituents and compositional ratios of hybrid liposomes. 3,4) In the course of our study on hybrid liposomes, the following interesting results were obtained. (a) Stereochemical control of the enantioselective hydrolysis of amino acid esters could be established by temperature regulation and by changing the composition of hybrid liposomes.…”

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confidence: 84%

“…The tumor cells (5.0ϫ10 4 viable cells/ml) were cultured for 48 h in an incubator at 37°C after adding the sample solutions. WST-1 solutions were added and the absorbance at wavelength of 450 nm was measured by spectrophotometer.…”

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confidence: 99%

“…(a) Stereochemical control of the enantioselective hydrolysis of amino acid esters could be established by temperature regulation and by changing the composition of hybrid liposomes. [3][4][5] (b) Inhibitory effects of hybrid liposomes including flavonoids 6) or antitumor drugs 7,8) on the growth of tumor cells in vitro and in vivo have been obtained. (c) High inhibitory effects on the growth of glioma cells in vitro using three-component hybrid liposomes containing sugar surfactants have been obtained without drugs.…”

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Induction of Apoptosis by Hybrid Liposomes for Human Breast Tumor Cells along with Activation of Caspases

Nagami

Matsumoto

Ueoka

2006

Biological & Pharmaceutical Bulletin

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It is well known that liposomes are used as drug carriers: examples are antitumor agents, hormones, and immunomodulation. 1,2) On the other hand, we have recently produced specific hybrid liposomes composed of vesicular and micellar molecules; they are stable for a longer period. The physical properties of these liposomes such as size, membrane fluidity, phase transition temperature, and hydrophobicity can be controlled by changing the constituents and compositional ratios of hybrid liposomes. 3,4) In the course of our study on hybrid liposomes, the following interesting results were obtained. (a) Stereochemical control of the enantioselective hydrolysis of amino acid esters could be established by temperature regulation and by changing the composition of hybrid liposomes. 9) (d) No toxicity of the hybrid liposomes was observed in normal cells in vitro nor in normal rats in vivo. 8,10) In this study, we report on hybrid liposomes composed of L-a -dimyristoylphosphatidylcholine (DMPC) and polyoxyethylenedodecyl ether (C 12 (EO) n : CH 3 (CH 2 ) 11 O(CH 2 CH 2 O) n H) having inhibitory effects on the growth of human breast tumor cells (MDA-MB-453) in vitro along with apoptosis.Hybrid liposomes were prepared by sonication (VELVO VS-N300, 300W) of a mixture containing 95 mol% DMPC and 5 mol% C 12 (EO) n in 5% glucose solution at 45°C with 300W, followed by filtration with a 0.20 mm filter.First, we examined the fifty percent inhibitory concentration (IC 50 ) of hybrid liposomes (HL-n) on the growth of MDA-MB-453 cells in vitro on the basis of WST-1 assay. 11)The tumor cells (5.0ϫ10 4 viable cells/ml) were cultured for 48 h in an incubator at 37°C after adding the sample solutions. WST-1 solutions were added and the absorbance at wavelength of 450 nm was measured by spectrophotometer. The inhibitory concentration was evaluated by A mean / A control , where A mean and A control denote the absorbance of water-soluble formazan, which was useful as an indicator of cell viability, in the presence and absence of sample solutions, respectively. The results are shown in Fig. 1. The IC 50 values of HL-n were from one seventh to a half of those of the DMPC liposomes, indicating that the inhibitory effects of hybrid liposomes are large when compared with those of the DMPC liposomes.Morphology of hybrid liposomes (HL-n) was examined on the basis of dynamic light scattering measurements. Hydrodynamic diameter (d hy ) of HL-n was 80-120 (HL-21 and 23) and 90-110 nm (HL-25), which remained stable for more than three weeks. On the other hand, it was found that DMPC liposomes, HL-4 and HL-10 were unstable. It is worthy to note that HL-n (nϭ21, 23, 25) having a diameter of 100 nm could avoid the clearance by reticular endothelial system in vivo. 12)Second, we examined the mechanism for inhibiting the growth of MDA-MB-453 cells in vitro. Fluorescence micrographs of MDA-MB-453 cells using TUNEL method after the treatment with hybrid liposomes are shown in Fig. 2. The green color (FITC) was observed in the cells after adding hybrid lipos...

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Induction of Apoptosis by Hybrid Liposomes for Human Breast Tumor Cells along with Activation of Caspases

Nagami

Matsumoto

Ueoka

2006

Biological & Pharmaceutical Bulletin

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“…Hybrid Liposomes (HL) made of vesicular and micellar molecules are nano-sized liposomal particles and can be processed without contamination of the organic solvent unlike traditional liposomes [6]. Studies of HL made of DMPC and polyoxyethylene (n) dodecyl ethers (C 12 (EO) n ) on the in vitro [7][8][9] and in vivo [9][10][11][12] development of lymphoma cells, and clinical applications [12] without drugs have already been reported.…”

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Apoptotic and Anti-invasive Effects of Hybrid Liposomes without Drugs against Human Breast Cancer Cells In Vitro

Ichihara¹,

Motomura²,

Matsumoto³

2017

J Nanomedine Biotherapeutic Discov

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“…18 The physical properties of hybrid liposomes, such as shape, size, membrane fluidity, and the temperature of the phase transition, can be controlled by changing the constituents and compositional ratios. 19 In the drug delivery system (DDS) study, the therapeutic effects of an anti-tumor drug, 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU), encapsulated into hybrid liposomes composed of L-R-dimyristoylphosphatidylcholine (DMPC) and polyoxyethylene (20) sorbitan monolaurate (Tween 20) have been observed for the meningeal gliomatosis model rats in vivo. 20 On the other hand, we have reported that hybrid liposomes (HL-n) composed of DMPC and polyoxyethylene(n) dodecyl ethers (C 12 (EO) n ) without any drugs inhibited the proliferation of various cancer cells along with apoptosis in vitro 21-23 and in vivo.…”

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Membrane-Targeted Nanotherapy with Hybrid Liposomes for Tumor Cells Leading to Apoptosis

Komizu

Nakata

Goto

et al. 2011

ACS Med. Chem. Lett.

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Hybrid liposomes are nanosized liposomal particles and can be prepared by sonication of vesicular and micellar molecules in a buffer solution. In this study, we obtained the first successful experiment resulting in a good correlation between inhibitory effects of hybrid liposomes on the growth of various tumor cells and the membrane fluidity of tumor cells (plasma membranes). The results indicated that hybrid liposomes could provide the possibility of novel membrane-targeted nanotherapy for intractable cancers.

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Membrane matrix for the hydrolysis of amino acid esters with marked enantioselectivity

Cited by 155 publications

References 0 publications

Induction of Apoptosis by Hybrid Liposomes for Human Breast Tumor Cells along with Activation of Caspases

Induction of Apoptosis by Hybrid Liposomes for Human Breast Tumor Cells along with Activation of Caspases

Apoptotic and Anti-invasive Effects of Hybrid Liposomes without Drugs against Human Breast Cancer Cells In Vitro

Membrane-Targeted Nanotherapy with Hybrid Liposomes for Tumor Cells Leading to Apoptosis

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