Synthesis and structural characterization of 6I,6II-diamino-6I,6II-dideoxy-cyclomaltoheptaose, a difunctionalized β-cyclodextrin

Blasio, Benedetto Di; Galdiero, Stefania; Pedone, Carlo; Benedetti, Ettore; Rizzarelli, Enrico; Pedotti, Sonia; Vecchio, Graziella; Gibbons, William A.

doi:10.1016/0008-6215(95)00357-6

Cited by 27 publications

(18 citation statements)

References 29 publications

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“…The ABCDSAH 2 was synthesized from the 6A,6B-diamino,6A,6B-dideoxy-b-cyclodextrin previously characterized [46], in very high yield (about 96%) and purity was tested by 1 H NMR spectra. The new ligand AB-CDSAH 2 was characterized in methanol by NMR, UV, ESI-MS and circular dichroism spectroscopy.…”

Section: The Ligandmentioning

confidence: 99%

Bioconjugates of cyclodextrins of manganese salen-type ligand with superoxide dismutase activity

Puglisi

Tabbı̀

Vecchio

2004

Journal of Inorganic Biochemistry

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Section: The Ligandmentioning

confidence: 99%

Bioconjugates of cyclodextrins of manganese salen-type ligand with superoxide dismutase activity

Puglisi

Tabbı̀

Vecchio

2004

Journal of Inorganic Biochemistry

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“…l-Carnosine methyl ester (bAHMe) was synthesized from l-carnosine ( bAH; (Sigma) with HCl in MeOH at 08 and AcCl as HCl source. The 6 A -amino-6 A -deoxy-b-cyclodextrin was synthesized as reported for the 6 A ,6 B -diamino-6 A ,6 B -dideoxy-b-cyclodextrin [56] Pulse Radiolysis. Pulse radiolysis was performed with electron pulses (ca.…”

Section: Experimental Partmentioning

confidence: 99%

Synthesis of New Carnosine Derivatives ofβ-Cyclodextrin and Their Hydroxyl Radical Scavenger Ability

Mendola

Sortino

Vecchio

et al. 2002

HCA

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Several in vitro and in vivo studies have suggested that carnosine can act as a scavenger of reactive oxygen species and intracellular proton buffer. On the other hand, carnosinase is a specific peptidase able to destroy the biological active dipeptide. To overcome this constraint, b-cyclodextrin (b-CD) was functionalized with carnosine to give the following new compounds:. Pulse-radiolysis investigation showed that the b-CD derivatives 1 ± 3 are excellent scavengers of OH . radicals. Their activity is not only due to the formation of the stable imidazole-centered radical, but also to the scavenger ability of the glucose moieties of the macrocycle (Scheme). This effect is independent of the disposition of the imidazole ring. In fact, the quenching constant values are similar for the three compounds.Introduction. ± Cyclodextrins (CDs), cyclic oligomers of a-d-glucopyranose, have attracted interest in a variety of contexts [1 ± 7], which include studies of their role in the realization of delivery systems [6 ± 12]. This is also reflected in the increasing number of patents in this field. Drug targeting commonly involves the use of cyclomaltosaccharides as CD inclusion complexes [7 ± 13]. It has been pointed out that the use of CD as a drug carrier may sometimes provide a simple, cheap, and effective strategy to increase drug solubility [6] [7] [12] [13], stability [6] [7] [12] [13], and photostability [14 ± 16] to modulate drug photoreactivity as well as to minimize the photoinduced toxic effects of a drug on biosubstrates [17] [18]. The bio-availability and effectiveness of the drug itself [6] [7] [12] may also be improved, especially in the case of lipophilic drugs. Cyclodextrin complexation has proved promising in stabilizing and increasing the absorption of growth hormones [19], interleukin-2 [19], aspartame [20], albumine [21], g-globuline [21], cyclosporine A [22], calcitonin [23], and insulin [6] [24] [25]. Rapid plasma clearance and problems regarding immunogenicity [6 ± 8] may limit the practical use of peptides or proteins of therapeutic importance. The covalent linkage of bioactive peptides to cyclodextrins has recently been proposed as a means of achieving good results in terms of solubility and reduced catabolism [26 ± 35]. The data reported support an interest in developing the design and investigation of such molecules. Biological peptides such as enkephalin [26] [31], enkephalin analogue DPDPE [33], neuropeptide substance P [30], and gastrin peptides [27] have been grafted onto CDs.

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“…CD derivatives were detected on TLC by UV and by an anisaldehyde test. 2A‐Disulfonated β‐cyclodextrin was synthesised as reported elsewhere16 and purified by reversed‐phase chromatography using a linear gradient H 2 O/MeOH as the eluent 17…”

Section: Methodsmentioning

confidence: 99%

Coordination Properties of 3‐Functionalised β‐Cyclodextrins: Thermodynamic Stereoselectivity of Copper(II) Complexes of the 3‐Histamine Derivative and Its Exploitation in Ligand‐Exchange Capillary Electrophoresis

et al. 2013

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A histamine derivative of β-cyclodextrin functionalised at the secondary rim was synthesised and characterised by optical and NMR spectroscopy. Its binary systems both with proton and copper(II) were thermodynamically characterised through pH-metric potentiometry. In addition, the ternary systems with the enantiomers of tryptophan, phenylalanine[a] 377 and alanine were investigated. Thermodynamic stereoselectivity was observed for both the tryptophan and phenylalanine enantiomers. The properties of the synthesised cyclodextrin derivative as a chiral selector were verified in chiral ligand-exchange capillary electrophoresis (CLECE) towards the enantiomeric pairs of some amino acids.

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Synthesis and structural characterization of 6I,6II-diamino-6I,6II-dideoxy-cyclomaltoheptaose, a difunctionalized β-cyclodextrin

Cited by 27 publications

References 29 publications

Bioconjugates of cyclodextrins of manganese salen-type ligand with superoxide dismutase activity

Bioconjugates of cyclodextrins of manganese salen-type ligand with superoxide dismutase activity

Synthesis of New Carnosine Derivatives ofβ-Cyclodextrin and Their Hydroxyl Radical Scavenger Ability

Coordination Properties of 3‐Functionalised β‐Cyclodextrins: Thermodynamic Stereoselectivity of Copper(II) Complexes of the 3‐Histamine Derivative and Its Exploitation in Ligand‐Exchange Capillary Electrophoresis

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