[1] Neoglycoproteins from synthetic glycopeptides

Kunz, Horst; Bruch, Karsten von dem

doi:10.1016/s0076-6879(94)47003-0

Cited by 11 publications

(4 citation statements)

References 38 publications

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“…The solid-phase synthesis of glycopeptides commonly relies on conventional peptide synthesis methods and the incorporation of glycosylated amino acid building blocks since direct glycosylation of oligopeptides on the polymer was often problematic . Different trichloroacetimidate galactosamine and glucosamine donors were used to elaborate monoglycosylated threonine residues within an octapeptide chain on standard Rink-PEGA resin .…”

Section: Glycosyl Trichloroacetimidatesmentioning

confidence: 99%

Solid-Phase Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries

2000

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Section: Glycosyl Trichloroacetimidatesmentioning

confidence: 99%

Solid-Phase Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries

2000

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“…Importantly, replacement of the N -methyl group of oxycodone and hydrocodone with an N -butyl group possessing a succinamic acid moiety allowed the haptens to be conjugated to tetanus toxoid (TT) under standard amide-coupling conditions (Supporting Information Figures 1 and 2). − We selected TT as our carrier protein due to its demonstrated efficacy in vaccines against drugs of abuse. − After conjugation, both Oxy-TT and Hydro-TT were formulated with alum (Alhydrogel, Invivogen) and CpG ODN 1826 as adjuvants, which have likewise demonstrated good efficacy in the course of our previous studies. ,,, …”

mentioning

confidence: 99%

An Advance in Prescription Opioid Vaccines: Overdose Mortality Reduction and Extraordinary Alteration of Drug Half-Life

et al. 2016

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Prescription opioids (POs) such as oxycodone and hydrocodone are highly effective medications for pain management, yet they also present a substantial risk for abuse and addiction. The consumption of POs has been escalating worldwide, resulting in tens of thousands of deaths due to overdose each year. Pharmacokinetic strategies based upon vaccination present an attractive avenue to suppress PO abuse. Herein, the preparation of two active PO vaccines is described that were found to elicit high-affinity antiopioid antibodies through a structurally congruent drug-hapten design. Administration of these vaccines resulted in a significant blockade of opioid analgesic activity, along with an unprecedented increase in drug serum half-life and protection against lethal overdose.

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“…The syntheses are multistep and use D-galactose as a starting material. The chemistry of glycopeptides in general and of O-glycopeptides especially, was reviewed [24][25][26][27] and will not be discussed here in more detail.…”

Section: Introductionmentioning

confidence: 99%

Solid phase synthesis of glycopeptide dendrimers with Tn antigenic structure and their biological activities. Part I

Ježek¹,

Velek²,

Vepřek³

et al. 1999

J. Peptide Sci.

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Multiple antigenic peptides containing dimeric Tn antigen [Ac-(Tn) 2 -k-Abu] 4 -(Lys-X) 2 -Lys-i-Ala (V: X= 0; VIII: X= k-Abu) and [Ac-(Tn) 2 -k-Abu] 8 -(Lys-X) 4 -(Lys-X) 2 -Lys-i-Ala (XI: X=0; XIV: X=k-Abu), immobilized on biocompatible Tenta Gel S NH 2 support were prepared by SPPS. Rosetting tests of V, VIII, XI and XIV showed positive reactions with anti-Tn (DAKO) and Tn+ erythrocytes, with anti-Tn/A (BRIC 66) and Tn+ and A erythrocytes, other combinations were negative. In all the animals immunized with XIV, we found a remarkable increase in the level of anti-Tn (titre 2000 -64000, score 105 -167) and no change of anti-A levels (titre 8, score 13-17). Neither non-immune nor immune sera showed any reactivity with T + , Cad + and blood group O erythrocytes. Immunized mice did not exhibit any sign of adverse reaction to the administered conjugates. Biological activities were correlated with molecular modelling and molecular dynamic calculations. The biological activities of these synthetic Tn antigen conjugates (good availability for the immunological interactions, highly specific immunogenicity, good biological tolerance) together with their precise chemical characterization seem to be a promising approach to preparation of anti-tumour vaccine and affinity purification of anti-Tn antibodies.

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[1] Neoglycoproteins from synthetic glycopeptides

Cited by 11 publications

References 38 publications

Solid-Phase Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries

Solid-Phase Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries

An Advance in Prescription Opioid Vaccines: Overdose Mortality Reduction and Extraordinary Alteration of Drug Half-Life

Solid phase synthesis of glycopeptide dendrimers with Tn antigenic structure and their biological activities. Part I

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