Mark Wentland

Summary

Affiliation: Rensselaer Polytechnic Institute
Country: USA

Publications

  1. ncbi request reprint 3-Carboxamido analogues of morphine and naltrexone. synthesis and opioid receptor binding properties
    M P Wentland
    Department of Chemistry, Rensselaer Polytechnic Institute, 110 8th Street, 12180, Troy, NY, USA
    Bioorg Med Chem Lett 11:1717-21. 2001
  2. pmc Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 8. High affinity ligands for opioid receptors in the picomolar Ki range: oxygenated N-(2-[1,1'-biphenyl]-4-ylethyl) analogues of 8-CAC
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 22:7340-4. 2012
  3. pmc Syntheses of novel high affinity ligands for opioid receptors
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 19:2289-94. 2009
  4. doi request reprint Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 7: syntheses and opioid receptor properties of cyclic variants of cyclazocine
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, 110 8th St, Troy, NY 12180, USA
    Bioorg Med Chem Lett 19:365-8. 2009
  5. doi request reprint Syntheses and opioid receptor binding properties of carboxamido-substituted opioids
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 19:203-8. 2009
  6. pmc Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 6: Opioid receptor binding properties of cyclic variants of 8-carboxamidocyclazocine
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem 16:5653-64. 2008
  7. ncbi request reprint Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. 4. Opioid receptor binding properties of 8-[N-(4'-phenyl)-phenethyl)carboxamido] analogues of cyclazocine and ethylketocycalzocine
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, New York 12180, USA
    J Med Chem 49:5635-9. 2006
  8. ncbi request reprint Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 3: 8-Thiocarboxamido and 8-thioformamido derivatives of cyclazocine
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 15:2547-51. 2005
  9. ncbi request reprint Synthesis and opioid receptor binding properties of a highly potent 4-hydroxy analogue of naltrexone
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 15:2107-10. 2005
  10. ncbi request reprint Selective protection and functionalization of morphine: synthesis and opioid receptor binding properties of 3-amino-3-desoxymorphine derivatives
    M P Wentland
    Department of Chemistry, Rensselaer Polytechnic Institute, Troy, New York 12180, USA
    J Med Chem 43:3558-65. 2000

Collaborators

Detail Information

Publications19

  1. ncbi request reprint 3-Carboxamido analogues of morphine and naltrexone. synthesis and opioid receptor binding properties
    M P Wentland
    Department of Chemistry, Rensselaer Polytechnic Institute, 110 8th Street, 12180, Troy, NY, USA
    Bioorg Med Chem Lett 11:1717-21. 2001
    ..High affinity (K(i)=34 and 1.7nM) for mu opioid receptors was seen, however, the new targets were 39- and 11-fold less potent than morphine and naltrexone, respectively...
  2. pmc Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 8. High affinity ligands for opioid receptors in the picomolar Ki range: oxygenated N-(2-[1,1'-biphenyl]-4-ylethyl) analogues of 8-CAC
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 22:7340-4. 2012
    ..A number of new analogues were made having single-digit pM affinity for the μ receptor. The most potent was the 3',4'-methylenedioxy analogue 18 (K(i)=1.6 pM)...
  3. pmc Syntheses of novel high affinity ligands for opioid receptors
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 19:2289-94. 2009
    ....
  4. doi request reprint Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 7: syntheses and opioid receptor properties of cyclic variants of cyclazocine
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, 110 8th St, Troy, NY 12180, USA
    Bioorg Med Chem Lett 19:365-8. 2009
    ..Compared to 2, many of the new compounds in this study displayed very high affinity for opioid receptors...
  5. doi request reprint Syntheses and opioid receptor binding properties of carboxamido-substituted opioids
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 19:203-8. 2009
    ..The active metabolite of tramadol and its carboxamide counterpart had comparable affinities for the three receptors...
  6. pmc Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 6: Opioid receptor binding properties of cyclic variants of 8-carboxamidocyclazocine
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem 16:5653-64. 2008
    ..In addition to the results from this study strongly supporting this pharmacophore hypothesis, a number of novel compounds with high affinity to opioid receptors have been identified...
  7. ncbi request reprint Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. 4. Opioid receptor binding properties of 8-[N-(4'-phenyl)-phenethyl)carboxamido] analogues of cyclazocine and ethylketocycalzocine
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, New York 12180, USA
    J Med Chem 49:5635-9. 2006
    ..High binding affinity to mu, kappa, and delta opioid receptors was observed for the 8-[N-(4'-phenyl)-phenethyl)carboxamido] analogue...
  8. ncbi request reprint Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 3: 8-Thiocarboxamido and 8-thioformamido derivatives of cyclazocine
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 15:2547-51. 2005
    ..High affinity for opioid receptors was observed for the 8-CSNH2 and 8-NHCHS analogues indicating that these groups are isosteric with not only the 8-OH but with the previously synthesized 8-CONH2 and 8-NHCHO cyclazocine derivatives...
  9. ncbi request reprint Synthesis and opioid receptor binding properties of a highly potent 4-hydroxy analogue of naltrexone
    Mark P Wentland
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 15:2107-10. 2005
    ..g., K(i)=0.052nM for mu) has been observed in the rationally designed naltrexone analogue 5. SAR and physical data supports the hypothesis that the 4-OH group of 5 stabilizes the 3-carboxamido group in the putative bioactive conformation...
  10. ncbi request reprint Selective protection and functionalization of morphine: synthesis and opioid receptor binding properties of 3-amino-3-desoxymorphine derivatives
    M P Wentland
    Department of Chemistry, Rensselaer Polytechnic Institute, Troy, New York 12180, USA
    J Med Chem 43:3558-65. 2000
    ....
  11. ncbi request reprint 8-Carboxamidocyclazocine analogues: redefining the structure-activity relationships of 2,6-methano-3-benzazocines
    M P Wentland
    Department of Chemistry, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 11:623-6. 2001
    ..41 and 0.53 nM, respectively) nearly comparable to cyclazocine. A high enantiopreference ((2R,6R,11R)-) for binding was also observed. Compound (+/-)-15 also displayed potent antinociception activity in mice when administered icv...
  12. ncbi request reprint Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 2: 8-formamidocyclazocine analogues
    Mark P Wentland
    Department of Chemistry, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 13:1911-4. 2003
    ..A preliminary SAR revealed that affinity is very sensitive to substitution on the formamide appendage...
  13. ncbi request reprint Syntheses and opioid receptor binding affinities of 8-amino-2,6-methano-3-benzazocines
    Mark P Wentland
    Department of Chemistry, Rensselaer Polytechnic Institute, Troy, New York 12180, USA
    J Med Chem 46:838-49. 2003
    ..Several derivatives were shown to have intrinsic opioid-receptor-mediated activity in [(35)S]GTPgammaS assays...
  14. pmc Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. 5. Opioid receptor binding properties of N-((4'-phenyl)-phenethyl) analogues of 8-CAC
    Melissa A VanAlstine
    Department of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Bioorg Med Chem Lett 17:6516-20. 2007
    ..High binding affinity to all three opioid receptors were observed for the N-(2-naphthylethyl) analogue of 8-CAC...
  15. ncbi request reprint Synthesis and pharmacology of 8-amino-3-[(tetrahydro-2-furanyl)methyl] benzomorphan
    Qun Zhou
    Department of Chemistry, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
    Yao Xue Xue Bao 38:748-53. 2003
    ..To design and synthesize new chiral 8-(substituted) amino-analogues of 3-[(tetrahydro-2-furanyl)methyl] benzomorphans, to expand knowledge of the structure-activity relationship (SAR) for 8-aminobenzomorphan...
  16. ncbi request reprint 10-Ketomorphinan and 3-substituted-3-desoxymorphinan analogues as mixed kappa and micro opioid ligands: synthesis and biological evaluation of their binding affinity at opioid receptors
    Ao Zhang
    Alcohol and Drug Abuse Research Center, McLean Hospital, Harvard Medical School, 115 Mill Street, Belmont, Massachusetts 02478, USA
    J Med Chem 47:165-74. 2004
    ..The high affinity of these carboxamido analogues, along with their greater lipophilicity and metabolic stability, make them promising candidates for further pharmacological investigation...
  17. pmc CC12, a high-affinity ligand for [3H]cimetidine binding, is an improgan antagonist
    Lindsay B Hough
    Center for Neuropharmacology and Neuroscience, Albany Medical College MC 136, 47 New Scotland Avenue, Albany, NY 12208, USA
    Neuropharmacology 52:1244-55. 2007
    ..Elucidation of this mechanism will enhance understanding of the biochemistry of pain relief...
  18. ncbi request reprint 8-Carboxamidocyclazocine: a long-acting, novel benzomorphan
    Jean M Bidlack
    Department of Pharmacology and Physiology, School of Medicine and Dentistry, University of Rochester, 601 Elmwood Avenue, Rochester, NY 14642 8711, USA
    J Pharmacol Exp Ther 302:374-80. 2002
    ..8-Carboxamidocyclazocine is a novel, long-acting benzomorphan, which possesses pharmacological properties that are distinct from the properties of cyclazocine...
  19. ncbi request reprint Effects of the mixed-action kappa/mu opioid agonist 8-carboxamidocyclazocine on cocaine- and food-maintained responding in rhesus monkeys
    Glenn W Stevenson
    Alcohol and Drug Abuse Research Center, McLean Hospital Harvard Medical School, 115 Mill Street, Belmont, MA 02478, USA
    Eur J Pharmacol 506:133-41. 2004
    ..However, non-selective effects of 8-CAC on food-maintained responding and tolerance to 8-CAC effects on cocaine self-administration may limit its potential for the treatment of cocaine dependence...

Research Grants14

  1. AMINOBENZOMORPHAN: POTENTIAL COCAINE ABUSE MEDICATIONS
    Mark Wentland; Fiscal Year: 2009
    ..Radioligand binding, [35S]GTPvS, and mouse antinociceptive assays will be used to characterize new targets pharmacologically. ..
  2. AMINOBENZOMORPHAN: POTENTIAL COCAINE ABUSE MEDICATIONS
    Mark Wentland; Fiscal Year: 2007
    ..Radioligand binding, [35S]GTPvS, and mouse antinociceptive assays will be used to characterize new targets pharmacologically. ..
  3. AMINOBENZOMORPHAN: POTENTIAL COCAINE ABUSE MEDICATIONS
    Mark Wentland; Fiscal Year: 2006
    ..Radioligand binding, [35 S]GTP-gamma-S, and mouse antinociceptive assays will be used to characterize new targets pharmacologically. ..
  4. AMINOBENZOMORPHAN: POTENTIAL COCAINE ABUSE MEDICATIONS
    Mark Wentland; Fiscal Year: 2001
    ..The characterization of novel cyclazocine derivatives will identify potential medications for treating cocaine and heroin abuse and will suggest the basic mechanisms responsible for the drug's action. ..
  5. 2,5 CYCLOHEXADIENONES IN NATURAL PRODUCTS SYNTHESIS
    Mark Wentland; Fiscal Year: 2001
    ....
  6. AMINOBENZOMORPHAN: POTENTIAL COCAINE ABUSE MEDICATIONS
    Mark Wentland; Fiscal Year: 2009
    ..Radioligand binding, [35S]GTPvS, and mouse antinociceptive assays will be used to characterize new targets pharmacologically. ..