A Facile Synthesis of Polyglycidyl Ethers from Polyols and Epichlorohydrin

Kida, Toshiyuki; Yokota, Mitsuru; Masuyama, Araki; Nakatsuji, Yohji; Okahara, Mitsuo

doi:10.1055/s-1993-25890

Cited by 24 publications

(25 citation statements)

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“…The triol 1,1,1-tris(hydroxymethyl)ethane 1 (0.427 g, 3.56 mmol) and KOH (1.803 g, 32.13 mmol) in DMSO as solvent (10 mL) were stirred until complete dissolution at 25°C, and the (±) epichlorohydrin (2.950 g, 31.88 mmol) was then added dropwise for 1 h. After complete addition, stirring was continued for 24 h at 30°C. The purification was performed following a well-established procedure [28]. It gave 0.996 mg of 2 as a pale yellow oil (95% yield i.e., 6.98 mmol), triglycidyl ether 2 (0.439 g, 1.522 mmol) and TBAB (0.150 g, 0.44 mmol) was added to absolute ethanol (12 mL) and the solution was stirred for 20 h at 28°C.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Surface‐Active Properties, and Antimicrobial Activities of New Neutral and Cationic Trimeric Surfactants

Murguía

Cristaldi

Porto

et al. 2008

J Surfact & Detergents

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Neutral and cationic series of new trimeric b-hydroxy amino or ammonium surfactants were synthesized via a two-step process involving the Williamson etherification and regioselective oxirane ring opening with primary and tertiary amines, which afforded good to excellent yields. The synthesized compounds were obtained in high purity by a simple purification procedure on column chromatography. The critical micelle concentration (CMC), effectiveness of surface tension reduction (c CMC ), surface excess concentration (C), and area per molecule at the interface (A) were determined and values indicate that the cationic series is characterized by good surface-active and self-aggregation properties. The antimicrobial activities are reported for the first time against representative bacteria and fungi for trimeric compounds. The antimicrobial potency was found to be dependent on the target microorganism (Gram-positive bacteria [ fungi [ Gram-negative bacteria), as well as both the neutral or ionic nature (cationic [ neutral) and alkyl chain length (tri-C 12 [ tri-C 18 [ tri-C 8 ) of the compounds. The tri-C 8 and tri-C 18 compounds were found to be almost inactive and the tri-C 12 compounds, the most potent antimicrobial surface-active agents from the synthesized series. The trimeric C 12 cationic compound was found to be comparable to benzalkonium chloride against Gram-positive bacteria and fungi, in vitro. The antimicrobial effectiveness of this new compound and the facile two-step procedure for synthesizing it with an excellent overall yield (92%) provide a cost effective trimeric gemini surfactant.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Surface‐Active Properties, and Antimicrobial Activities of New Neutral and Cationic Trimeric Surfactants

Murguía

Cristaldi

Porto

et al. 2008

J Surfact & Detergents

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“…[15]. Briefly, 1 ml of Feridex (11.2 mg/ml) was added to a solution containing 1.6 ml of KOH, 0.7 ml of double-distilled H 2 O (ddH 2 O), and 0.7 ml of epichlorohydrin [19]. The mixture was reacted for 12 hours with constant shaking.…”

Section: Cell Sourcesmentioning

confidence: 99%

Fluorophore-Conjugated Iron Oxide Nanoparticle Labeling and Analysis of Engrafting Human Hematopoietic Stem Cells

et al. 2007

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The use of nanometer-sized iron oxide particles combined with molecular imaging techniques enables dynamic studies of homing and trafficking of human hematopoietic stem cells (HSC). Identifying clinically applicable strategies for loading nanoparticles into primitive HSC requires strictly defined culture conditions to maintain viability without inducing terminal differentiation. In the current study, fluorescent molecules were covalently linked to dextrancoated iron oxide nanoparticles (Feridex) to characterize human HSC labeling to monitor the engraftment process. Conjugating fluorophores to the dextran coat for fluorescence-activated cell sorting purification eliminated spurious signals from nonsequestered nanoparticle contaminants. A short-term defined incubation strategy was developed that allowed efficient labeling of both quiescent and cycling HSC, with no discernable toxicity in vitro or in vivo. Transplantation of purified primary human cord blood lineage-depleted and CD34؉ cells into immunodeficient mice allowed detection of labeled human HSC in the recipient bones. Flow cytometry was used to precisely quantitate the cell populations that had sequestered the nanoparticles and to follow their fate post-transplantation. Flow cytometry endpoint analysis confirmed the presence of nanoparticle-labeled human stem cells in the marrow. The use of fluorophorelabeled iron oxide nanoparticles for fluorescence imaging in combination with flow cytometry allows evaluation of labeling efficiencies and homing capabilities of defined human HSC subsets. STEM CELLS 2008;26:517-524 Disclosure of potential conflicts of interest is found at the end of this article.

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“…The best results were obtained using a procedure developed by Kida et al 21 for the synthesis of polyglycidyl derivatives. The reaction was carried out in DMSO with KOH at room temperature.…”

Section: Synthesis Of Oxiranesmentioning

confidence: 99%

Synthesis of racemic and optically active glycidic ethers, precursors of liquid crystalline polyethers

Taton

Borgne²,

Chen³

et al. 1998

Chirality

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A Facile Synthesis of Polyglycidyl Ethers from Polyols and Epichlorohydrin

Cited by 24 publications

References 0 publications

Synthesis, Surface‐Active Properties, and Antimicrobial Activities of New Neutral and Cationic Trimeric Surfactants

Synthesis, Surface‐Active Properties, and Antimicrobial Activities of New Neutral and Cationic Trimeric Surfactants

Fluorophore-Conjugated Iron Oxide Nanoparticle Labeling and Analysis of Engrafting Human Hematopoietic Stem Cells

Synthesis of racemic and optically active glycidic ethers, precursors of liquid crystalline polyethers

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