The Cyclodextrins and Their Application in Environmental Biotechnology

Szejtli, J.

doi:10.1016/s0166-1116(08)70344-3

Cited by 8 publications

(6 citation statements)

References 8 publications

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“…9 Fortunately, the CD solubility in water can be significantly increased by the addition of a small number of substituents to the hydroxyl groups of the anhydroglucose monomers. 10 Different CDs have previously been evaluated for their ability to improve the solubility and bioavailability of protease inhibitors. Boudad et al have described saquinavir-hydroxypropylβ-cyclodextrin (HPBCD, molar substitution ) 3) preparations and their incorporation into poly(alkylcyanoacrylate) nanoparticles.…”

Section: Introductionmentioning

confidence: 99%

Pharmacokinetics of Saquinavir After Intravenous and Oral Dosing of Saquinavir: Hydroxybutenyl-β-Cyclodextrin Formulations

Buchanan

Edgar

et al. 2007

Biomacromolecules

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The current research evaluated the ability of hydroxybutenyl-beta-cyclodextrin (HBenBCD) to enhance saquinavir in vitro solubility and in vivo oral bioavailability; both the base and mesylate salt forms of saquinavir were investigated. HBenBCD was effective and significantly improved saquinavir solubility in aqueous media. In the presence of 10 wt % HBenBCD, saquinavir base solubility in water was increased to ca. 5.5 +/- 0.4 mg/mL and represents a 27-fold increase from that observed in water (207 +/- 5 microg/mL) in the absence of HBenBCD. Saquinavir-HBenBCD formulations were found to have rapid dissolution over a wide pH range (1.2-6.8), and saquinavir solubility in these media was maintained throughout the experiments. When saquinavir-HBenBCD formulations were administered to Wistar-Hannover rats, saquinavir was rapidly absorbed and rapidly eliminated. Rapid saquinavir elimination was particularly pronounced when saquinavir-HBenBCD formulations were given as an oral aqueous gavage. Saquinavir oral bioavailability in rats obtained from saquinavir mesylate capsules (2.0% +/- 0.7%) was increased (9 +/- 4)-fold (18.6% +/- 7.3%) when dosed with saquinavir base-HBenBCD capsules. Clearly, HBenBCD can significantly improve the solubility and oral bioavailability of saquinavir; however, further formulation studies are required to optimize saquinavir oral delivery using this technology.

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Section: Introductionmentioning

confidence: 99%

Pharmacokinetics of Saquinavir After Intravenous and Oral Dosing of Saquinavir: Hydroxybutenyl-β-Cyclodextrin Formulations

Buchanan

Edgar

et al. 2007

Biomacromolecules

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“…Cyclodextrins are cyclic nonreducing oligosaccharides consisting of 6±12 glucose units linked by a-1,4-glycosidic bonds (Fujiwara et al, 1992). Due to their capability in forming inclusion complexes with a wide variety of compounds by encapsulation, cyclodextrins have found applications in the food, pharmaceutical, cosmetic, and agricultural industries (Szejtli, 1990;Tonkova, 1998). Cyclodextrins can be produced from polysaccharides such as starch by enzymatic conversion with cyclodextrin glucanotransferase (EC 2.4.1.…”

Section: Introductionmentioning

confidence: 99%

Anchorage of cyclodextrin glucanotransferase on the outer membrane of Escherichia coli

Wan

Chang

Lin

2002

Biotech & Bioengineering

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The gene encoding cyclodextrin glucanotransferase (CGTase) was successfully cloned from B. macerans by PCR. A recombinant plasmid pCS005 with a gene encoding the Lpp-OmpA-CGTase trifusion protein was constructed and transformed into E. coli for the surface display of CGTase. Results of immunoblotting analysis and protease accessibility on the fractionated cell membranes confirmed that the Lpp-OmpA-CGTase trifusion protein was successfully anchored on the outer membrane of E. coli. However, only 50% of the membrane-anchored trifusion proteins were displayed on the outer surface of E. coli with the remaining 50% un-translocated. The low efficiency of surface display is attributed to the large size of CGTase. Only a trace amount of CGTase activity was detected for both the whole cells and the cell debris fractions. Because the results of the protease accessibility study suggested that the trypsin-resistant conformation of CGTase was preserved in the membrane-anchored CGTase, we believe that the lack of enzyme activity is mainly due to the inaccessibility of the CGTase active site, near the N-terminus, for substrate molecules. It can be estimated that the critical size for surface display of protein in E. coli is approximately 70 kDa.

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“…In turn, hydrophilic parts of the guest molecule remain as far outside the complex cavity as possible to maximize contact with the polar solvent. These complexes include proteins and amino acids that contain aromatic side chains [i.e., phenylalanine @he), tyrosine (Tyr), and tryptophan (Try)] [2]. Recently, cyclodextrins have been used in the separation of dansylated amino acids by micellar electrokinetic capillary chromatography [3] and with the chiral separation of dansylated amino acids by capillary zone electrophoresis (CZE) [4].…”

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confidence: 99%

False positives and the detection of cyclodextrin inclusion complexes by electrospray mass spectrometry

Cunniff

Vouros

1995

J. Am. Soc. Mass Spectrom.

137

108

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The results of previous works that have claimed to detect cyclodextrin inclusion complexes via the "soft" ionization technique of electrospray ionization mass spectrometry are revisited. A more extensive study of cyclodextrin mixtures with amino acids and small peptides demonstrates that amino acid and peptide "complexes" are detected by electrospray mass spectrometry regardless of the presence (or not) of an aromatic moiety on the side chain. Amino acids that may be least likely to form hydrophobic inclusion complexes with cyclodextrin in solution generally show the most intense complex ions. The data suggest that these "complexes" are, in all likelihood, electrostatic adducts formed during the electrospray process. Systematic controls are suggested to ensure that "false positives" do not negate many of the claims concerning the detection of solution-derived noncovalent compounds.

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The Cyclodextrins and Their Application in Environmental Biotechnology

Cited by 8 publications

References 8 publications

Pharmacokinetics of Saquinavir After Intravenous and Oral Dosing of Saquinavir: Hydroxybutenyl-β-Cyclodextrin Formulations

Pharmacokinetics of Saquinavir After Intravenous and Oral Dosing of Saquinavir: Hydroxybutenyl-β-Cyclodextrin Formulations

Anchorage of cyclodextrin glucanotransferase on the outer membrane of Escherichia coli

False positives and the detection of cyclodextrin inclusion complexes by electrospray mass spectrometry

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