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Examining the effects of vitamin B12 conjugation on the biological activity of insulin: a molecular dynamic and in vivo oral uptake investigation
Journal article   Peer reviewed

Examining the effects of vitamin B12 conjugation on the biological activity of insulin: a molecular dynamic and in vivo oral uptake investigation

S. Clardy-James, D.G. Allis, T.J. Fairchild and R.P. Doyle
MedChemComm, Vol.3(9), pp.1054-1058
2012
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Abstract

The practical use of the vitamin B 12 uptake pathway to orally deliver peptides and proteins is much debated. To understand the full potential of the pathway however, a deeper understanding of the impact B 12 conjugation has on peptides and proteins is needed. We previously reported an orally active B 12 based insulin conjugate attached at LysB29 with hypoglycemic properties in STZ diabetic rats. We are exploring an alternative attachment for B 12 on insulin in an attempt to determine the effect B 12 has on the protein biological activity. We describe herein the synthesis, characterization, and purification of a new B 12-insulin conjugate, which is attached between the B 12 ribose hydroxyl group and insulin PheB1. The hypoglycemic properties resulting from oral administration (gavage) of such a conjugate in STZ diabetic rats was similar to that noted in a conjugate covalently linked at insulin LysB29, demonstrating the availability of both positions on insulin for B 12 attachment. A possible rationale for this result is put forward from MD simulations. We also conclude that there is a dose dependent response that can be observed for B 12-insulin conjugates, with doses of conjugate greater than 10 -9 M necessary to observe even low levels of glucose drop.

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Collaboration types
Domestic collaboration
International collaboration
Citation topics
2 Chemistry
2.276 Metalloenzymes
2.276.1947 Radical Enzymes
Web Of Science research areas
Biochemistry & Molecular Biology
Chemistry, Medicinal
ESI research areas
Pharmacology & Toxicology
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