Cyclodextrin as Carrier of Peptide Hormones. Conformational and Biological Properties of β-Cyclodextrin/Gastrin Constructs

Schaschke, Norbert; Fiori, Stella; Weyher, Elisabeth; Escrieut, Chantal; Fourmy, Daniel; Müller, Gerhard; Moröder, Luis

doi:10.1021/ja973852g

Cited by 55 publications

(42 citation statements)

References 58 publications

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“…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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confidence: 99%

“…There is, however, little recent data available for the biological properties of these systems. Some of the biological properties of tetra-and heptapeptides bonded to b-CD, i.e., of artificial receptor agonists of the CCK-B/gastrin receptor, have been reported [27]. The enzymatic digestion rate of these bioconjugates with proteases has been tested and, in some cases, increased stability has been reported [27].…”

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confidence: 99%

“…Some of the biological properties of tetra-and heptapeptides bonded to b-CD, i.e., of artificial receptor agonists of the CCK-B/gastrin receptor, have been reported [27]. The enzymatic digestion rate of these bioconjugates with proteases has been tested and, in some cases, increased stability has been reported [27]. Slow enzymatic-degradation rates in plasma have also been reported for substance P derivatives [30].…”

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

Mendola

Sortino

Vecchio

et al. 2002

HCA

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“…In 1998, Moroder and coworkers 82 reported an extensive study of -cyclodextrin as carrier of peptide hormones by mono-or multivalent display. The C-terminal tetrapeptide amide sequence (H-Trp-NleAsp-Phe-NH 2 ) of the gastrointestinal hormone gastrin is the shortest sequence capable of exhibiting all of the biological properties, although with reduced potency.…”

Section: Cyclo-dextrin-peptide Conjugatesmentioning

confidence: 99%

Carbohydrates in peptide and protein design

Jensen¹,

Brask²

2005

Biopolymers

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Monosaccharides and amino acids are fundamental building blocks in the assembly of nature's polymers. They have different structural aspects and, to a significant extent, different functional groups. Oligomerization gives rise to oligosaccharides and peptides, respectively. While carbohydrates and peptides can be found conjoined in nature, e.g., in glycopeptides, the aim of this review is the radical redesign of peptide structures using carbohydrates, particularly monosaccharides and cyclic oligosaccharides, to produce novel peptides, peptidomimetics, and abiotic proteins. These hybrid molecules, chimeras, have properties arising largely from the combination of structural characteristics of carbohydrates with the functional group diversity of peptides. This field includes de novo designed synthetic glycopeptides, sugar (carbohydrate) amino acids, carbohydrate scaffolds for nonpeptidal peptidomimetics of cyclic peptides, cyclodextrin functionalized peptides, and carboproteins, i.e., carbohydrate-based proteinmimetics. These successful applications demonstrate the general utility of carbohydrates in peptide and protein architecture. #

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“…The propounded mechanism suggests that the molecules in the cavity are capable of interacting with different species in solution, which may be captured, thus forming inclusion complexes [14]. The CDs belong to the cyclic oligosaccharides family, compounded and structured by several d-glucopyranose units, which are held together by (1 -4)-glucosidic bonds.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Characterization and Determination of Mercury Using Carbon Paste Electrodes Modified with Cyclodextrins

et al. 2005

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In this work the characterization and determination of mercury in HClO 4 media using carbon paste electrodes modified with a-and b-cyclodextrins (CPE a-CD and CPE b-CD ) at E d ¼À 0.7 V with a t d ¼ 20 s and a potential scan v ¼ 20 mV s À1 is studied.. The statistical results obtained indicate that the modified electrodes displayed a better analytical performance as compared to that obtained with the unmodified CPE. The detection limits for the CPE a-CD and for the CPE b-CD were 0.05 and 0.09 mM, respectively, while for the CPE it was 0.41 mM. The CPE b-CD exhibited greater sensitivity as compared to that of the CPE a-CD .

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Cyclodextrin as Carrier of Peptide Hormones. Conformational and Biological Properties of β-Cyclodextrin/Gastrin Constructs

Cited by 55 publications

References 58 publications

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

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

Carbohydrates in peptide and protein design

Electrochemical Characterization and Determination of Mercury Using Carbon Paste Electrodes Modified with Cyclodextrins

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