Methyl sulfonamide substituents improve the pharmacokinetic properties of bicyclic 2-pyridone based Chlamydia trachomatis inhibitors

Chlamydia trachomatis infections are a global health problem and new approaches to treat C. trachomatis with drugs of high specificity would be valuable. A library of substituted ring fused 2-pyridones has been synthesized and evaluated for their ability to attenuate C. trachomatis infectivity. In v...

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Published inMedChemComm Vol. 10; no. 11; pp. 1966 - 1987
Main Authors Kulen, Martina, Nunez-Otero, Carlos, Cairns, Andrew G., Silver, Jim, Lindgren, Anders E. G., Wede, Emma, Singh, Pardeep, Vielfort, Katarina, Bahnan, Wael, Good, James A. D., Svensson, Richard, Bergstrom, Sven, Gylfe, Asa, Almqvist, Fredrik
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2019
Royal Society of Chemistry
Subjects
Bacteria
Bioavailability
Biochemistry & Molecular Biology
Biopharmaceuticals
Cell permeability
Chemistry
Chemistry, Medicinal
Chlamydia
Chlamydia trachomatis
Condoms
Evaluation
Global health
In vivo methods and tests
Infectivity
Life Sciences & Biomedicine
Metabolism
Oral administration
Organic compounds
Permeability
Pharmacokinetics
Pharmacology
Pharmacology & Pharmacy
Science & Technology
Sexually transmitted diseases
Solubility
STD
Sulfonamides
DESIGN
MECHANISMS
PROTEIN
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Abstract Chlamydia trachomatis infections are a global health problem and new approaches to treat C. trachomatis with drugs of high specificity would be valuable. A library of substituted ring fused 2-pyridones has been synthesized and evaluated for their ability to attenuate C. trachomatis infectivity. In vivo pharmacokinetic studies were performed, with the best candidates demonstrating that a C8-methylsulfonamide substituent improved pharmacokinetic properties important for oral administration. C8-Methyl sulfonamide analogue 30 inhibited C. trachomatis infectivity in low micromolar concentrations. Further pharmacokinetic evaluation at an oral dose of 10 mg kg(-1) showed an apparent bioavailability of 41%, compared to C8-cyclopropyl and -methoxy analogues which had negligible oral uptake. In vitro ADME (absorption, distribution, metabolism and excretion) testing of solubility and Caco-2 cell permeability revealed that both solubility and permeability is greatly improved with the C8-methyl sulfonamide 30, effectively moving it from BCS (Biopharmaceutical Classification System) class IV to II.
AbstractList Chlamydia trachomatis infections are a global health problem and new approaches to treat C. trachomatis with drugs of high specificity would be valuable. A library of substituted ring fused 2-pyridones has been synthesized and evaluated for their ability to attenuate C. trachomatis infectivity. In vivo pharmacokinetic studies were performed, with the best candidates demonstrating that a C8-methylsulfonamide substituent improved pharmacokinetic properties important for oral administration. C8-Methyl sulfonamide analogue 30 inhibited C. trachomatis infectivity in low micromolar concentrations. Further pharmacokinetic evaluation at an oral dose of 10 mg kg−1 showed an apparent bioavailability of 41%, compared to C8-cyclopropyl and -methoxy analogues which had negligible oral uptake. In vitro ADME (absorption, distribution, metabolism and excretion) testing of solubility and Caco-2 cell permeability revealed that both solubility and permeability is greatly improved with the C8-methyl sulfonamide 30, effectively moving it from BCS (Biopharmaceutical Classification System) class IV to II.
Chlamydia trachomatis infections are a global health problem and new approaches to treat C. trachomatis with drugs of high specificity would be valuable. A library of substituted ring fused 2-pyridones has been synthesized and evaluated for their ability to attenuate C. trachomatis infectivity. In vivo pharmacokinetic studies were performed, with the best candidates demonstrating that a C8-methylsulfonamide substituent improved pharmacokinetic properties important for oral administration. C8-Methyl sulfonamide analogue 30 inhibited C. trachomatis infectivity in low micromolar concentrations. Further pharmacokinetic evaluation at an oral dose of 10 mg kg(-1) showed an apparent bioavailability of 41%, compared to C8-cyclopropyl and -methoxy analogues which had negligible oral uptake. In vitro ADME (absorption, distribution, metabolism and excretion) testing of solubility and Caco-2 cell permeability revealed that both solubility and permeability is greatly improved with the C8-methyl sulfonamide 30, effectively moving it from BCS (Biopharmaceutical Classification System) class IV to II.
Chlamydia trachomatis infections are a global health problem and new approaches to treat C. trachomatis with drugs of high specificity would be valuable. A library of substituted ring fused 2-pyridones has been synthesized and evaluated for their ability to attenuate C. trachomatis infectivity. In vivo pharmacokinetic studies were performed, with the best candidates demonstrating that a C8-methylsulfonamide substituent improved pharmacokinetic properties important for oral administration. C8-Methyl sulfonamide analogue 30 inhibited C. trachomatis infectivity in low micromolar concentrations. Further pharmacokinetic evaluation at an oral dose of 10 mg kg −1 showed an apparent bioavailability of 41%, compared to C8-cyclopropyl and -methoxy analogues which had negligible oral uptake. In vitro ADME (absorption, distribution, metabolism and excretion) testing of solubility and Caco-2 cell permeability revealed that both solubility and permeability is greatly improved with the C8-methyl sulfonamide 30 , effectively moving it from BCS (Biopharmaceutical Classification System) class IV to II.
Methyl sulfonamide substituents effectively improve the pharmacokinetic properties of bicyclic 2-pyridones, a new class of Chlamydia trachomatis infectivity inhibitors. Chlamydia trachomatis infections are a global health problem and new approaches to treat C. trachomatis with drugs of high specificity would be valuable. A library of substituted ring fused 2-pyridones has been synthesized and evaluated for their ability to attenuate C. trachomatis infectivity. In vivo pharmacokinetic studies were performed, with the best candidates demonstrating that a C8-methylsulfonamide substituent improved pharmacokinetic properties important for oral administration. C8-Methyl sulfonamide analogue 30 inhibited C. trachomatis infectivity in low micromolar concentrations. Further pharmacokinetic evaluation at an oral dose of 10 mg kg –1 showed an apparent bioavailability of 41%, compared to C8-cyclopropyl and -methoxy analogues which had negligible oral uptake. In vitro ADME (absorption, distribution, metabolism and excretion) testing of solubility and Caco-2 cell permeability revealed that both solubility and permeability is greatly improved with the C8-methyl sulfonamide 30 , effectively moving it from BCS (Biopharmaceutical Classification System) class IV to II.
infections are a global health problem and new approaches to treat with drugs of high specificity would be valuable. A library of substituted ring fused 2-pyridones has been synthesized and evaluated for their ability to attenuate infectivity. pharmacokinetic studies were performed, with the best candidates demonstrating that a C8-methylsulfonamide substituent improved pharmacokinetic properties important for oral administration. C8-Methyl sulfonamide analogue inhibited infectivity in low micromolar concentrations. Further pharmacokinetic evaluation at an oral dose of 10 mg kg showed an apparent bioavailability of 41%, compared to C8-cyclopropyl and -methoxy analogues which had negligible oral uptake. ADME (absorption, distribution, metabolism and excretion) testing of solubility and Caco-2 cell permeability revealed that both solubility and permeability is greatly improved with the C8-methyl sulfonamide , effectively moving it from BCS (Biopharmaceutical Classification System) class IV to II.
Author Gylfe, Asa
Kulen, Martina
Silver, Jim
Bahnan, Wael
Good, James A. D.
Wede, Emma
Cairns, Andrew G.
Singh, Pardeep
Nunez-Otero, Carlos
Vielfort, Katarina
Almqvist, Fredrik
Lindgren, Anders E. G.
Bergstrom, Sven
Svensson, Richard
AuthorAffiliation c Department of Molecular Biology , Umeå University , 901 87 Umeå , Sweden
a Department of Chemistry , Umeå University , 901 87 Umeå , Sweden . Email: fredrik.almqvist@umu.se
d Laboratory for Molecular Infection Medicine Sweden (MIMS) , Umeå University , 901 87 Umeå , Sweden
f The Uppsala University Drug Optimization and Pharmaceutical Profiling Platform , Department of Pharmacy , Uppsala University , SE-751 23 Uppsala , Sweden
b Umeå Centre for Microbial Research , Umeå University , 901 87 Umeå , Sweden . Email: sven.bergstrom@umu.se ; Email: asa.gylfe@umu.se
e Department of Clinical microbiology , Umeå University , 901 85 Umeå , Sweden
g SciLifeLab Drug Discovery and Development Platform , ADME of Therapeutics Facility , Uppsala University , SE-751 23 Uppsala , Sweden
AuthorAffiliation_xml – name: a Department of Chemistry , Umeå University , 901 87 Umeå , Sweden . Email: fredrik.almqvist@umu.se
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– name: d Laboratory for Molecular Infection Medicine Sweden (MIMS) , Umeå University , 901 87 Umeå , Sweden
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– sequence: 12
  givenname: Sven
  surname: Bergstrom
  fullname: Bergstrom, Sven
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These authors contributed equally.
Division of Infection Medicine, BMC, Lund University, Sweden.
ReViral Ltd, NETpark Plexus, Thomas Wright Way, Sedgefield, TS21 3FD, United Kingdom.
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Snippet Chlamydia trachomatis infections are a global health problem and new approaches to treat C. trachomatis with drugs of high specificity would be valuable. A...
infections are a global health problem and new approaches to treat with drugs of high specificity would be valuable. A library of substituted ring fused...
Chlamydia trachomatis infections are a global health problem and new approaches to treat C. trachomatis with drugs of high specificity would be valuable. A...
Methyl sulfonamide substituents effectively improve the pharmacokinetic properties of bicyclic 2-pyridones, a new class of Chlamydia trachomatis infectivity...
Source Web of Science
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pubmedcentral
proquest
crossref
pubmed
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SourceType Open Access Repository
Aggregation Database
Index Database
Enrichment Source
StartPage 1966
SubjectTerms Bacteria
Bioavailability
Biochemistry & Molecular Biology
Biopharmaceuticals
Cell permeability
Chemistry
Chemistry, Medicinal
Chlamydia
Chlamydia trachomatis
Condoms
Evaluation
Global health
In vivo methods and tests
Infectivity
Life Sciences & Biomedicine
Metabolism
Oral administration
Organic compounds
Permeability
Pharmacokinetics
Pharmacology
Pharmacology & Pharmacy
Science & Technology
Sexually transmitted diseases
Solubility
STD
Sulfonamides
Title Methyl sulfonamide substituents improve the pharmacokinetic properties of bicyclic 2-pyridone based Chlamydia trachomatis inhibitors
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https://www.ncbi.nlm.nih.gov/pubmed/32206238
https://www.proquest.com/docview/2314005957/abstract/
https://search.proquest.com/docview/2382662234
https://pubmed.ncbi.nlm.nih.gov/PMC7069368
https://urn.kb.se/resolve?urn=urn:nbn:se:umu:diva-166479
https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-400093
Volume 10
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