Literature DB >> 34342443

Optimization of the Urea Linker of Triazolopyridazine MMV665917 Results in a New Anticryptosporidial Lead with Improved Potency and Predicted hERG Safety Margin.

Edmund Oboh1, Tanner J Schubert1, Jose E Teixeira2, Erin E Stebbins2, Peter Miller2, Emily Philo1, Haresh Thakellapalli1, Scott D Campbell3, David W Griggs3,4, Christopher D Huston2, Marvin J Meyers1,4.   

Abstract

Cryptosporidiosis is caused by infection of the small intestine by Cryptosporidium parasites, resulting in severe diarrhea, dehydration, malabsorption, and potentially death. The only FDA-approved therapeutic is only partially effective in young children and ineffective for immunocompromised patients. Triazolopyridazine MMV665917 is a previously reported anti-Cryptosporidium screening hit with in vivo efficacy but suffers from modest inhibition of the hERG ion channel, which could portend cardiotoxicity. Herein, we describe our initial development of structure-activity relationships of this novel lead series with a particular focus on optimization of the piperazine-urea linker. We have discovered that piperazine-acetamide is a superior linker resulting in identification of SLU-2633, which has an EC50 of 0.17 μM, an improved projected margin versus hERG, prolonged pharmacokinetic exposure in small intestine, and oral efficacy in vivo with minimal systemic exposure. SLU-2633 represents a significant advancement toward the identification of a new effective and safe treatment for cryptosporidiosis.

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Year:  2021        PMID: 34342443      PMCID: PMC8792998          DOI: 10.1021/acs.jmedchem.1c01136

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   8.039


  44 in total

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Authors:  Xian-Ming Chen; Janet S Keithly; Carlos V Paya; Nicholas F LaRusso
Journal:  N Engl J Med       Date:  2002-05-30       Impact factor: 91.245

2.  Validation of IMP dehydrogenase inhibitors in a mouse model of cryptosporidiosis.

Authors:  Suresh Kumar Gorla; Nina N McNair; Guangyi Yang; Song Gao; Ming Hu; Venkatakrishna R Jala; Bodduluri Haribabu; Boris Striepen; Gregory D Cuny; Jan R Mead; Lizbeth Hedstrom
Journal:  Antimicrob Agents Chemother       Date:  2013-12-23       Impact factor: 5.191

3.  In-vitro activities of paromomycin and lasalocid evaluated in combination against Cryptosporidium parvum.

Authors:  X You; R F Schinazi; M J Arrowood; M Lejkowski; A S Juodawlkis; J R Mead
Journal:  J Antimicrob Chemother       Date:  1998-02       Impact factor: 5.790

4.  Effect of nitazoxanide on morbidity and mortality in Zambian children with cryptosporidiosis: a randomised controlled trial.

Authors:  Beatrice Amadi; Mwiya Mwiya; John Musuku; Angela Watuka; Sandie Sianongo; Ayman Ayoub; Paul Kelly
Journal:  Lancet       Date:  2002-11-02       Impact factor: 79.321

5.  A high-throughput phenotypic screen identifies clofazimine as a potential treatment for cryptosporidiosis.

Authors:  Melissa S Love; Federico C Beasley; Rajiv S Jumani; Timothy M Wright; Arnab K Chatterjee; Christopher D Huston; Peter G Schultz; Case W McNamara
Journal:  PLoS Negl Trop Dis       Date:  2017-02-03

6.  Necessity of Bumped Kinase Inhibitor Gastrointestinal Exposure in Treating Cryptosporidium Infection.

Authors:  Samuel L M Arnold; Ryan Choi; Matthew A Hulverson; Deborah A Schaefer; Sumiti Vinayak; Rama S R Vidadala; Molly C McCloskey; Grant R Whitman; Wenlin Huang; Lynn K Barrett; Kayode K Ojo; Erkang Fan; Dustin J Maly; Michael W Riggs; Boris Striepen; Wesley C Van Voorhis
Journal:  J Infect Dis       Date:  2017-07-01       Impact factor: 5.226

7.  P-Glycoprotein-Mediated Efflux Reduces the In Vivo Efficacy of a Therapeutic Targeting the Gastrointestinal Parasite Cryptosporidium.

Authors:  Samuel L M Arnold; Ryan Choi; Matthew A Hulverson; Grant R Whitman; Molly C Mccloskey; Carlie S Dorr; Rama S R Vidadala; Mansi Khatod; Mary Morada; Lynn K Barrett; Dustin J Maly; Nigel Yarlett; Wesley C Van Voorhis
Journal:  J Infect Dis       Date:  2019-08-30       Impact factor: 5.226

8.  Identification of a potent benzoxaborole drug candidate for treating cryptosporidiosis.

Authors:  Christopher S Lunde; Erin E Stebbins; Rajiv S Jumani; Md Mahmudul Hasan; Peter Miller; John Barlow; Yvonne R Freund; Pamela Berry; Rianna Stefanakis; Jiri Gut; Philip J Rosenthal; Melissa S Love; Case W McNamara; Eric Easom; Jacob J Plattner; Robert T Jacobs; Christopher D Huston
Journal:  Nat Commun       Date:  2019-06-27       Impact factor: 14.919

9.  A Cryptosporidium PI(4)K inhibitor is a drug candidate for cryptosporidiosis.

Authors:  Ujjini H Manjunatha; Sumiti Vinayak; Jennifer A Zambriski; Alexander T Chao; Tracy Sy; Christian G Noble; Ghislain M C Bonamy; Ravinder R Kondreddi; Bin Zou; Peter Gedeck; Carrie F Brooks; Gillian T Herbert; Adam Sateriale; Jayesh Tandel; Susan Noh; Suresh B Lakshminarayana; Siau H Lim; Laura B Goodman; Christophe Bodenreider; Gu Feng; Lijun Zhang; Francesca Blasco; Juergen Wagner; F Joel Leong; Boris Striepen; Thierry T Diagana
Journal:  Nature       Date:  2017-05-31       Impact factor: 49.962

10.  Amixicile Reduces Severity of Cryptosporidiosis but Does Not Have In Vitro Activity against Cryptosporidium.

Authors:  Luther A Bartelt; David T Bolick; Glynis L Kolling; Erin Stebbins; Christopher D Huston; Richard L Guerrant; Paul S Hoffman
Journal:  Antimicrob Agents Chemother       Date:  2018-11-26       Impact factor: 5.191

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  1 in total

1.  High-Throughput Screening of a Marine Compound Library Identifies Anti-Cryptosporidium Activity of Leiodolide A.

Authors:  Rachel M Bone Relat; Priscilla L Winder; Gregory D Bowden; Esther A Guzmán; Tara A Peterson; Shirley A Pomponi; Jill C Roberts; Amy E Wright; Roberta M O'Connor
Journal:  Mar Drugs       Date:  2022-03-30       Impact factor: 6.085

  1 in total

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