Derivatives Of α-Cyclodextrin and the Synthesis of 6-O-α-D-Glucopyranosyl-α-Cyclodextrin

Takeo, Ken’ichi; Ueraura, Kazuhiko; Mitoh, Hisayoshi

doi:10.1080/07328308808058926

Cited by 105 publications

(46 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…4). Compounds 8b and 8e were obtained as the hydrochloride salts by use of the same methods outlined for the synthesis of ␤-cyclodextrins, starting from the known hexakis (2,3-di-O-acetyl-6-deoxy-6-iodo)-␣-cyclodextrin 7 (29). The aminoethyl (compound 5a), aminopropyl (compound 5b), aminobutyl (compound 5c), and aminohexyl (compound 5e) derivatives of ␤-cyclodextrin (compound 8) were successfully guanidinylated with S-methylisothiourea hemisulfate and treated with 1 N HCl to afford ␤-cyclodextrin derivatives 9a to 9c and 9e as the hydrochloride salts (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…N-Bromoalkylphthalimides 1a to 1i were either commercially available or prepared according to procedures outlined in the literature (1,15). Peracetylated 6-iodo-␤-CD 3 and peracetylated 6-iodo-␣-CD 7 were prepared according to the methods of Baer et al (3) and Takeo et al (29). Per-6-amino-␤-CD and -␣-CD 15 and 16 (2,12) and cyclodextrins 17 and 18 (31) were prepared according to procedures outlined in the literature.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Search for Cyclodextrin-Based Inhibitors of Anthrax Toxins: Synthesis, Structural Features, and Relative Activities

Karginov

Nestorovich

Yohannes

et al. 2006

Antimicrob Agents Chemother

View full text Add to dashboard Cite

Recently, using structure-inspired drug design, we demonstrated that aminoalkyl derivatives of ␤-cyclodextrin inhibited anthrax lethal toxin action by blocking the transmembrane pore formed by the protective antigen (PA) subunit of the toxin. In the present study, we evaluate a series of new ␤-cyclodextrin derivatives with the goal of identifying potent inhibitors of anthrax toxins. Newly synthesized hepta-6-thioaminoalkyl and hepta-6-thioguanidinoalkyl derivatives of ␤-cyclodextrin with alkyl spacers of various lengths were tested for the ability to inhibit cytotoxicity of lethal toxin in cells as well as to block ion conductance through PA channels reconstituted in planar bilayer lipid membranes. Most of the tested derivatives were protective against anthrax lethal toxin action at low or submicromolar concentrations. They also blocked ion conductance through PA channels at concentrations as low as 0.1 nM. The activities of the derivatives in both cell protection and channel blocking were found to depend on the length and chemical nature of the substituent groups. One of the compounds was also shown to block the edema toxin activity. It is hoped that these results will help to identify a new class of drugs for anthrax treatment, i.e., drugs that block the pathway for toxin translocation into the cytosol, the PA channel.

show abstract

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Search for Cyclodextrin-Based Inhibitors of Anthrax Toxins: Synthesis, Structural Features, and Relative Activities

Karginov

Nestorovich

Yohannes

et al. 2006

Antimicrob Agents Chemother

View full text Add to dashboard Cite

show abstract

“…[5] for the analogous a-cyclodextrin derivative. 7.0 g tert-butyldimethylsilyl chloride (Fluka AG, CH-9008 Buchs, Switzerland), dissolved in 30 ml dry pyridine, was added dropwise over 10 min to a stirred solution of 5.0 g 8-cyclodextrin (Fluka AG, CH-9008 Buchs, Switzerland) and 3.95 g imidazole (Merck, Darmstadt, FRG) in 100 ml dry pyridine.…”

Section: Heptakis(6-0-tert -Butyld~rnethylsiiyl)-~-cyclodextrinmentioning

confidence: 99%

Stereoisomeric flavor compounds part. LV: Stereodifferentiation of some chiral volatiles on heptakis(2,3‐di‐O‐acetyl‐6‐O‐tert‐butyldimethylsilyl)‐β‐cyclodextrin

Dietrich

Maas

Karl

et al. 1992

J. High Resol. Chromatogr.

114

View full text Add to dashboard Cite

show abstract

“…After drying on MgSO 4 , the chloroform layer was evaporated until dryness. The residue was washed with a mixture of diethyl ether/n-pentane (1:1); mp, 154-1607C; yield, 81% [28][29][30]. The so obtained randomly methylated CDs were fractionated by flash silica gel column (ICN, Costa Mesa, CA, USA; 0.032-0.063 mm grain size) chromatography applying a gradient of ethyl acetate and methanol 1:0-1:1.…”

Section: Synthesis Of the Randomly Methylated CDmentioning

confidence: 99%

Chiral capillary electrophoresis: Facts and fiction on the reproducibility of resolution with randomly substituted cyclodextrins

2004

View full text Add to dashboard Cite

Comparative enantioseparation of the enantiomers of 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate was performed with cyclodextrin (CD)-modified capillary electrophoresis (CE). Two single isomers, beta-CD, heptakis(2,3,6-tri-O-methyl)-beta-CD (TM-beta-CD), and heptakis(2,6-di-O-methyl)-beta-CD (DM-beta-CD) of 98% purity as well as heptakis(2,3-di-O-acetyl)-beta-CD were used and compared in terms of resolution power to randomly methylated and corresponding acetylated beta-CDs, which were synthesized in our laboratory. The methylated ones were characterized by means of matrix-assisted laser desorption/ionization-time of flight-(MALDI-TOF) mass spectrometry. By testing defined mixtures of single isomers and comparing their resolution power to randomly substituted CDs of similar degree of substitution we could show, that a simple characterization by the average molecular degree of substitution (DS) is not sufficient. In order to get reproducible results, a clearly defined substitution pattern is necessary, which is not given using randomly substituted CDs. Taken together, a validation of a chiral separation with "undefined" CD derivatives is almost impossible.

show abstract

Derivatives Of α-Cyclodextrin and the Synthesis of 6-O-α-D-Glucopyranosyl-α-Cyclodextrin

Cited by 105 publications

References 23 publications

Search for Cyclodextrin-Based Inhibitors of Anthrax Toxins: Synthesis, Structural Features, and Relative Activities

Search for Cyclodextrin-Based Inhibitors of Anthrax Toxins: Synthesis, Structural Features, and Relative Activities

Stereoisomeric flavor compounds part. LV: Stereodifferentiation of some chiral volatiles on heptakis(2,3‐di‐O‐acetyl‐6‐O‐tert‐butyldimethylsilyl)‐β‐cyclodextrin

Chiral capillary electrophoresis: Facts and fiction on the reproducibility of resolution with randomly substituted cyclodextrins

Contact Info

Product

Resources

About