Norborn-2-en-7-ones as physiologically-triggered carbon monoxide-releasing prodrugs

A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3 a -bromo-norborn-2-en-7-one Diels–Alder cycloadducts of 2-bromomaleimides and 2,5-dimethyl-3,4-diphenylcyclopentadienone has been developed. Examples possessing protonated amine and diamine groups showed g...

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Published inChemical science (Cambridge) Vol. 8; no. 8; pp. 5454 - 5459
Main Authors Kueh, Jui Thiang Brian, Stanley, Nathan J., Hewitt, Russell J., Woods, Laura M., Larsen, Lesley, Harrison, Joanne C., Rennison, David, Brimble, Margaret A., Sammut, Ivan A., Larsen, David S.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.08.2017
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ISCHEMIA-REPERFUSION INJURY
THERAPEUTIC APPLICATIONS
HEME OXYGENASE
CARBONYLATION
MOLECULE
CORM-3
ANHYDRIDES
KIDNEY
TRANSPLANTATION
PROTECTS
Online AccessGet full text

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Abstract A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3 a -bromo-norborn-2-en-7-one Diels–Alder cycloadducts of 2-bromomaleimides and 2,5-dimethyl-3,4-diphenylcyclopentadienone has been developed. Examples possessing protonated amine and diamine groups showed good water solubility and thermal stability. Half-lives for CO-release in TRIS-sucrose buffer at pH 7.4 ranged from 19 to 75 min at 37 °C and 31 to 32 h at 4 °C. Bioavailability in rats was demonstrated by oral gavage and oCOm-21 showed a dose dependent vasorelaxant effect in pre-contracted rat aortic rings with an EC 50 of 1.6 ± 0.9 μM. Increased intracellular CO levels following oCOm-21 exposure were confirmed using a CO specific fluorescent probe.
AbstractList A prodrug strategy for the release of the gasotransmitter carbon monoxide (CO) at physiological pH, based upon 3 a -bromo-norborn-2-en-7-one Diels–Alder cycloadducts has been developed. A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3 a -bromo-norborn-2-en-7-one Diels–Alder cycloadducts of 2-bromomaleimides and 2,5-dimethyl-3,4-diphenylcyclopentadienone has been developed. Examples possessing protonated amine and diamine groups showed good water solubility and thermal stability. Half-lives for CO-release in TRIS-sucrose buffer at pH 7.4 ranged from 19 to 75 min at 37 °C and 31 to 32 h at 4 °C. Bioavailability in rats was demonstrated by oral gavage and oCOm-21 showed a dose dependent vasorelaxant effect in pre-contracted rat aortic rings with an EC 50 of 1.6 ± 0.9 μM. Increased intracellular CO levels following oCOm-21 exposure were confirmed using a CO specific fluorescent probe.
A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3a-bromonorborn-2-en-7-one Diels-Alder cycloadducts of 2-bromomaleimides and 2,5-dimethyl-3,4-diphenylcyclopentadienone has been developed. Examples possessing protonated amine and diamine groups showed good water solubility and thermal stability. Half-lives for CO-release in TRIS-sucrose buffer at pH 7.4 ranged from 19 to 75 min at 37 degrees C and 31 to 32 h at 4 degrees C. Bioavailability in rats was demonstrated by oral gavage and oCOm-21 showed a dose dependent vasorelaxant effect in pre-contracted rat aortic rings with an EC50 of 1.6 +/- 0.9 mu M. Increased intracellular CO levels following oCOm-21 exposure were confirmed using a CO specific fluorescent probe.
A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3 a -bromo-norborn-2-en-7-one Diels–Alder cycloadducts of 2-bromomaleimides and 2,5-dimethyl-3,4-diphenylcyclopentadienone has been developed. Examples possessing protonated amine and diamine groups showed good water solubility and thermal stability. Half-lives for CO-release in TRIS-sucrose buffer at pH 7.4 ranged from 19 to 75 min at 37 °C and 31 to 32 h at 4 °C. Bioavailability in rats was demonstrated by oral gavage and oCOm-21 showed a dose dependent vasorelaxant effect in pre-contracted rat aortic rings with an EC 50 of 1.6 ± 0.9 μM. Increased intracellular CO levels following oCOm-21 exposure were confirmed using a CO specific fluorescent probe.
A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3a-bromo-norborn-2-en-7-one Diels-Alder cycloadducts of 2-bromomaleimides and 2,5-dimethyl-3,4-diphenylcyclopentadienone has been developed. Examples possessing protonated amine and diamine groups showed good water solubility and thermal stability. Half-lives for CO-release in TRIS-sucrose buffer at pH 7.4 ranged from 19 to 75 min at 37 °C and 31 to 32 h at 4 °C. Bioavailability in rats was demonstrated by oral gavage and oCOm-21 showed a dose dependent vasorelaxant effect in pre-contracted rat aortic rings with an EC50 of 1.6 ± 0.9 μM. Increased intracellular CO levels following oCOm-21 exposure were confirmed using a CO specific fluorescent probe.A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3a-bromo-norborn-2-en-7-one Diels-Alder cycloadducts of 2-bromomaleimides and 2,5-dimethyl-3,4-diphenylcyclopentadienone has been developed. Examples possessing protonated amine and diamine groups showed good water solubility and thermal stability. Half-lives for CO-release in TRIS-sucrose buffer at pH 7.4 ranged from 19 to 75 min at 37 °C and 31 to 32 h at 4 °C. Bioavailability in rats was demonstrated by oral gavage and oCOm-21 showed a dose dependent vasorelaxant effect in pre-contracted rat aortic rings with an EC50 of 1.6 ± 0.9 μM. Increased intracellular CO levels following oCOm-21 exposure were confirmed using a CO specific fluorescent probe.
A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3 -bromo-norborn-2-en-7-one Diels-Alder cycloadducts of 2-bromomaleimides and 2,5-dimethyl-3,4-diphenylcyclopentadienone has been developed. Examples possessing protonated amine and diamine groups showed good water solubility and thermal stability. Half-lives for CO-release in TRIS-sucrose buffer at pH 7.4 ranged from 19 to 75 min at 37 °C and 31 to 32 h at 4 °C. Bioavailability in rats was demonstrated by oral gavage and showed a dose dependent vasorelaxant effect in pre-contracted rat aortic rings with an EC of 1.6 ± 0.9 μM. Increased intracellular CO levels following exposure were confirmed using a CO specific fluorescent probe.
Author Stanley, Nathan J.
Brimble, Margaret A.
Woods, Laura M.
Hewitt, Russell J.
Rennison, David
Sammut, Ivan A.
Harrison, Joanne C.
Kueh, Jui Thiang Brian
Larsen, David S.
Larsen, Lesley
AuthorAffiliation b Department of Pharmacology , University of Otago , Dunedin , New Zealand . Email: ivan.sammut@otago.ac.nz
c School of Chemical Sciences , University of Auckland , Auckland , New Zealand
a Department of Chemistry , University of Otago , Dunedin , New Zealand . Email: david.larsen@otago.ac.nz
AuthorAffiliation_xml – name: a Department of Chemistry , University of Otago , Dunedin , New Zealand . Email: david.larsen@otago.ac.nz
– name: b Department of Pharmacology , University of Otago , Dunedin , New Zealand . Email: ivan.sammut@otago.ac.nz
– name: c School of Chemical Sciences , University of Auckland , Auckland , New Zealand
Author_xml – sequence: 1
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  organization: Department of Chemistry, University of Otago, Dunedin, New Zealand
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  organization: Department of Chemistry, University of Otago, Dunedin, New Zealand
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  fullname: Rennison, David
  organization: School of Chemical Sciences, University of Auckland, Auckland, New Zealand
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  givenname: Margaret A.
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  surname: Brimble
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  givenname: Ivan A.
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  surname: Sammut
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  orcidid: 0000-0002-3563-1086
  surname: Larsen
  fullname: Larsen, David S.
  organization: Department of Chemistry, University of Otago, Dunedin, New Zealand
BackLink https://www.ncbi.nlm.nih.gov/pubmed/28970925$$D View this record in MEDLINE/PubMed
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Keywords ISCHEMIA-REPERFUSION INJURY
THERAPEUTIC APPLICATIONS
HEME OXYGENASE
CARBONYLATION
MOLECULE
CORM-3
ANHYDRIDES
KIDNEY
TRANSPLANTATION
PROTECTS
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Snippet A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3 a -bromo-norborn-2-en-7-one Diels–Alder cycloadducts of...
A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3a-bromonorborn-2-en-7-one Diels-Alder cycloadducts of...
A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3 -bromo-norborn-2-en-7-one Diels-Alder cycloadducts of...
A prodrug strategy for the release of the gasotransmitter CO at physiological pH, based upon 3a-bromo-norborn-2-en-7-one Diels-Alder cycloadducts of...
A prodrug strategy for the release of the gasotransmitter carbon monoxide (CO) at physiological pH, based upon 3 a -bromo-norborn-2-en-7-one Diels–Alder...
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Title Norborn-2-en-7-ones as physiologically-triggered carbon monoxide-releasing prodrugs
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