Literature DB >> 19954198

Glycosylated PROLI/NO derivatives as nitric oxide prodrugs.

Rahul S Nandurdikar1, Anna E Maciag, Sam Y Hong, Harinath Chakrapani, Michael L Citro, Larry K Keefer, Joseph E Saavedra.   

Abstract

GlcNAc-PROLI/NO prodrugs that are activated by N-acetylglucosaminidase to release nitric oxide (NO) are described. A classical acid-amine coupling is used to bifunctionalize these PROLI/NO prodrugs, which on activation generate up to 4 mol of NO, a peptide residue, and an N-acetylglucosamine residue. Many of the prodrugs synthesized are efficient sources of intracellular NO.

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Year:  2010        PMID： 19954198      PMCID： PMC2808138          DOI： 10.1021/ol902481s

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  17 in total

Review 1.  Nitric oxide donors: chemical activities and biological applications.

Authors:  Peng George Wang; Ming Xian; Xiaoping Tang; Xuejun Wu; Zhong Wen; Tingwei Cai; Adam J Janczuk
Journal:  Chem Rev       Date:  2002-04       Impact factor: 60.622

Review 2.  Final report on the safety assessment of Cocoyl Sarcosine, Lauroyl Sarcosine, Myristoyl Sarcosine, Oleoyl Sarcosine, Stearoyl Sarcosine, Sodium Cocoyl Sarcosinate, Sodium Lauroyl Sarcosinate, Sodium Myristoyl Sarcosinate, Ammonium Cocoyl Sarcosinate, and Ammonium Lauroyl Sarcosinate.

Authors:  R S Lanigan
Journal:  Int J Toxicol       Date:  2001       Impact factor: 2.032

Review 3.  Recent developments in nitric oxide donor drugs.

Authors:  M R Miller; I L Megson
Journal:  Br J Pharmacol       Date:  2007-04-02       Impact factor: 8.739

4.  Esterase-sensitive nitric oxide donors of the diazeniumdiolate family: in vitro antileukemic activity.

Authors:  J E Saavedra; P J Shami; L Y Wang; K M Davies; M N Booth; M L Citro; L K Keefer
Journal:  J Med Chem       Date:  2000-01-27       Impact factor: 7.446

5.  Diazeniumdiolate ions as leaving groups in anomeric displacement reactions: a protection-deprotection strategy for ionic diazeniumdiolates.

Authors:  Brett M Showalter; Melissa M Reynolds; Carlos A Valdez; Joseph E Saavedra; Keith M Davies; John R Klose; Gwendolyn N Chmurny; Michael L Citro; Joseph J Barchi; Scott I Merz; Mark E Meyerhoff; Larry K Keefer
Journal:  J Am Chem Soc       Date:  2005-10-19       Impact factor: 15.419

6.  Hantzsch 1,4-dihydropyridines containing a diazen-1-ium-1,2-diolate nitric oxide donor moiety to study calcium channel antagonist structure-activity relationships and nitric oxide release.

Authors:  Jeffrey-Tri Nguyen; Carlos A Velázquez; Edward E Knaus
Journal:  Bioorg Med Chem       Date:  2005-03-01       Impact factor: 3.641

Review 7.  Fluorescent and luminescent probes for measurement of oxidative and nitrosative species in cells and tissues: progress, pitfalls, and prospects.

Authors:  Peter Wardman
Journal:  Free Radic Biol Med       Date:  2007-07-10       Impact factor: 7.376

8.  Cell-permeable esters of diazeniumdiolate-based nitric oxide prodrugs.

Authors:  Harinath Chakrapani; Anna E Maciag; Michael L Citro; Larry K Keefer; Joseph E Saavedra
Journal:  Org Lett       Date:  2008-10-29       Impact factor: 6.005

9.  V-PROLI/NO, a prodrug of the nitric oxide donor, PROLI/NO.

Authors:  Harinath Chakrapani; Brett M Showalter; Li Kong; Larry K Keefer; Joseph E Saavedra
Journal:  Org Lett       Date:  2007-07-20       Impact factor: 6.005

10.  Hydrolytic reactivity trends among potential prodrugs of the O2-glycosylated diazeniumdiolate family. Targeting nitric oxide to macrophages for antileishmanial activity.

Authors:  Carlos A Valdez; Joseph E Saavedra; Brett M Showalter; Keith M Davies; Thomas C Wilde; Michael L Citro; Joseph J Barchi; Jeffrey R Deschamps; Damon Parrish; Stefan El-Gayar; Ulrike Schleicher; Christian Bogdan; Larry K Keefer
Journal:  J Med Chem       Date:  2008-06-06       Impact factor: 7.446
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  2 in total

1.  "Click" reaction in conjunction with diazeniumdiolate chemistry: developing high-load nitric oxide donors.

Authors:  Oyebola A Oladeinde; Sam Y Hong; Ryan J Holland; Anna E Maciag; Larry K Keefer; Joseph E Saavedra; Rahul S Nandurdikar
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

2.  Nitrogen-bound diazeniumdiolated amidines.

Authors:  Debanjan Biswas; Jeffrey R Deschamps; Larry K Keefer; Joseph A Hrabie
Journal:  Chem Commun (Camb)       Date:  2010-06-30       Impact factor: 6.222
  2 in total

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