Extraordinary micellar enantioselectivity coupled to altered aggregate structure

Ueoka, Ryuichi; Moss, Robert A.; Swarup, Shanti; Matsumoto, Yōko; Strauss, George; Murakami, Yukito

doi:10.1021/ja00293a067

Cited by 79 publications

(28 citation statements)

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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%

“…(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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confidence: 99%

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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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confidence: 84%

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confidence: 99%

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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“…54 Hybrid liposomes composed of L-a-dimyristoylphosphatidylcholine (DMPC) and polyoxyethylene(n)dodecyl ether (C 12 (EO) n ) were able to inhibit the proliferation of and induce apoptosis in human CRC cells in vitro. [55][56][57] Intravenous administration of DMPC/ C 12 (EO) n or DMPC/docosahexaenoic acid hybrid liposomes into a liver metastases mouse model of xenografted human CRC exhibited significant therapeutic effects.…”

Section: Hybrid Liposomesmentioning

confidence: 99%

Application of liposomes in drug development – focus on gastroenterological targets

Zhang¹,

Wang²,

Mao³

et al. 2013

IJN

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Over the past decade, liposomes became a focal point in developing drug delivery systems. New liposomes, with novel lipid molecules or conjugates, and new formulations opened possibilities for safely and efficiently treating many diseases including cancers. New types of liposomes can prolong circulation time or specifically deliver drugs to therapeutic targets. This article concentrates on current developments in liposome based drug delivery systems for treating diseases of the gastrointestinal tract. We will review different types and uses of liposomes in the development of therapeutics for gastrointestinal diseases including inflammatory bowel diseases and colorectal cancer.

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“…14) Yoshida et al have studied metastasis mechanism of cancer cells 15,16) and for clinical applications of immunotherapy using CD3-and lymphokine interleukin (IL)2-activated killer (CD3-LAK) cells. On the other hand, Ueoka et al have investigated inhibitory effects of hybrid liposomes 17,18) composed of phosphatidylcholine and polyoxyethylenealkyl ether on the growth of tumor cells in vitro, in vivo, and for clinical applications. [19][20][21] On the basis of these studies for cancer, we have tried to develop new immunotherapy using TTZ which is molecular target drug.…”

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Therapeutic Effects of Autologous Lymphocytes Activated with Trastuzumab for Xenograft Mouse Models of Human Breast Cancer

Nakagawa

Matsuoka

Ichihara

et al. 2013

Biological & Pharmaceutical Bulletin

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Trastuzumab (TTZ) is molecular targeted drug used for metastatic breast cancer patients overexpressing human epidermal growth factor receptor 2 (HER2). Therapeutic effects of lymphocytes activated with TTZ (TTZ-LAK). p185 HER2 has partial homology with the epidermal growth factor receptor and shares intrinsic tyrosine kinase activity with that receptor. HER2 overexpressed in human breast cancers correlated with poor clinical outcome in women with breast cancers.1-3) HER2 is known as epidermal growth factor receptor (ErbB) 2 of the tyrosine kinase (TK) receptor, belonging to ErbB growth factor receptor family. There are four members of HER family receptors; epidermal growth factor receptor (EGFR)/ErbB1/ HER1, HER2/ErbB2, HER3/ErbB3, and HER/ErbB4.3) HER family receptors are activated by ligand-induced dimerization, or receptor pairing. Dimerization is a critical step in HER family-mediated signaling, and HER receptors are able to homodimerize or heterodimerize with other HER family members. HER2 is the preferred dimerization partner for all HER family receptors. However, there are no known endogenous ligands that bind to HER2. 4)The extracellular domain of HER2 is in a conformation that is open and ready for dimerization. So, molecules such as monoclonal antibodies would bind to the extracellular domain of HER2 to suppress those activity. Several monoclonal antibodies (mAbs) directed against HER2 ectodomain that specifically inhibit the growth of tumor cell lines overexpressing HER2 have been developed. 5) Trastuzumab (TTZ) is a humanized immunoglobulin G1 kappa (IgG1κ) light chain mAb in which the complementary-determining regions (CDR) of a HER2-specific mouse mAb were joined to in human immunoglobulin variable regions.5) TTZ binds to the domain IV of the extracellular segment of the HER2/neu receptor. Because TTZ belong to IgG1, its effects may be related to Fab (antigen binding fragment) or Fc (crystallizable fragment) regions.6) It has been reported that antibody-dependent cellular cytotoxicity (ADCC) plays an important role in the antitumor activity of TTZ. 7) Although the mechanisms underlying the action of TTZ are still not fully understood, inhibitory effects of TTZ by cell cycle arrest in G1 and induction of apoptosis on the growth of HER2-positive breast cancer cells in vitro have been reported.8) The combination chemotherapy with TTZ has been shown to improve survival for women with HER2-overexpressing metastatic breast cancer patients. [9][10][11] However, there were severe side-effects in combination chemotherapy. 1,6,12,13) On the other hand, immunotherapy using lymphocyte stimulated with immunomodulators such as cytokines was noted in cancer therapy as attractive approach, since there is no serious side effects in immunotherapy. Significant prolongation in survival and disease free period in group of immunotherapy compared with no-treatment group have been reported. 14)Yoshida et al. have studied metastasis mechanism of cancer cells 15,16) and for clinical applications of immunotherapy using CD3-a...

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Extraordinary micellar enantioselectivity coupled to altered aggregate structure

Cited by 79 publications

References 2 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

Application of liposomes in drug development – focus on gastroenterological targets

Therapeutic Effects of Autologous Lymphocytes Activated with Trastuzumab for Xenograft Mouse Models of Human Breast Cancer

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Extraordinary micellar enantioselectivity coupled to altered aggregate structure

Cited by 79 publications

References 2 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

Application of liposomes in drug development &ndash; focus on gastroenterological targets

Therapeutic Effects of Autologous Lymphocytes Activated with Trastuzumab for Xenograft Mouse Models of Human Breast Cancer

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Application of liposomes in drug development – focus on gastroenterological targets