Document Detail


Engineering prolonged-acting prodrugs employing an albumin-binding probe that undergoes slow hydrolysis at physiological conditions.
MedLine Citation:
PMID:  19883707     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Here we describe the design and application of OSu-FMS-MAL-S-(CH(2))(15)-COOH, an agent that associates with albumin while linked to a peptide or a protein with sufficient affinity (Ka=2 to 2.6 x 10(5)M(-1)) to protract the action of short- lived peptides and proteins in vivo. Under physiological conditions this probe undergoes spontaneous hydrolysis with the concomitant reactivation of inactive conjugates. Intravenously administered (125)I-labeled-Insulin-FMS-MAL-S-(CH(2))(15)-COOH to rats shows half-life of 17+/-2h, exceeding 5.2 times that obtained with intravenously administered (125)I-labeled Insulin. In mice this derivative facilitates glucose-lowering effect over a period of 24h, yielding AUC five times greater than that obtained by a similar dose of insulin-detemir. Similarly, subcutaneous administration of Exendin-4-FMS-MAL-S-(CH(2))(15)-COOH into mice facilitated prolonged and stable reduction in glucose level, yielding a t(1/2) value of 28+/-2h, exceeding the effect of exendin-4 4.7 folds. The inactive derivative gentamicin-FMS-MAL-S-(CH(2))(15)-COOH regained its full antibacterial potency upon incubation at physiological conditions yielding a t(1/2) value of 7.1+/-0.2h. In conclusion, the albumin-binding probe we introduced enables to prolong the action of any amino containing molecule in vivo, without the drawback of inactivation that often occurs upon such derivatization.
Authors:
K Sasson; Y Marcus; V Lev-Goldman; S Rubinraut; M Fridkin; Y Shechter
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Publication Detail:
Type:  Journal Article     Date:  2009-10-30
Journal Detail:
Title:  Journal of controlled release : official journal of the Controlled Release Society     Volume:  142     ISSN:  1873-4995     ISO Abbreviation:  J Control Release     Publication Date:  2010 Mar 
Date Detail:
Created Date:  2010-02-17     Completed Date:  2010-06-22     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8607908     Medline TA:  J Control Release     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  214-20     Citation Subset:  IM    
Copyright Information:
Copyright 2009 Elsevier B.V. All rights reserved.
Affiliation:
Department of Biological-Chemistry, The Weizmann Institute of Science, Rehovot 76100, Israel.
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MeSH Terms
Descriptor/Qualifier:
Amino Acid Sequence
Animals
Glucose / metabolism
Humans
Hydrolysis
Hypoglycemic Agents / administration & dosage*,  chemistry,  metabolism,  therapeutic use
Insulin / administration & dosage*,  chemistry,  metabolism,  therapeutic use
Mice
Molecular Sequence Data
Peptides / administration & dosage*,  chemistry,  metabolism,  therapeutic use
Prodrugs / administration & dosage*,  chemistry,  metabolism,  therapeutic use
Protein Binding
Rats
Serum Albumin / metabolism*
Venoms / administration & dosage*,  chemistry,  metabolism,  therapeutic use
Chemical
Reg. No./Substance:
0/Hypoglycemic Agents; 0/Peptides; 0/Prodrugs; 0/Serum Albumin; 0/Venoms; 11061-68-0/Insulin; 141732-76-5/exenatide; 50-99-7/Glucose

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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