Literature DB >> 18178091

Role of benzimidazole (Bid) in the delta-opioid agonist pseudopeptide H-Dmt-Tic-NH-CH(2)-Bid (UFP-502).

Severo Salvadori1, Stella Fiorini, Claudio Trapella, Frank Porreca, Peg Davis, Yusuke Sasaki, Akihiro Ambo, Ewa D Marczak, Lawrence H Lazarus, Gianfranco Balboni.   

Abstract

H-Dmt-Tic-NH-CH(2)-Bid (UFP-502) was the first delta-opioid agonist prepared from the Dmt-Tic pharmacophore. It showed interesting pharmacological properties, such as stimulation of mRNA BDNF expression and antidepression. To evaluate the importance of 1H-benzimidazol-2-yl (Bid) in the induction of delta-agonism, it was substituted by similar heterocycles: The substitution of NH(1) by O or S transforms the reference delta-agonist into delta-antagonists. Phenyl ring of benzimidazole is not important for delta-agonism; in fact 1H-imidazole-2-yl retains delta-agonist activity.

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Year:  2007        PMID： 18178091      PMCID： PMC2390930          DOI： 10.1016/j.bmc.2007.12.032

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  24 in total

1.  Effect of lysine at C-terminus of the Dmt-Tic opioid pharmacophore.

Authors:  Gianfranco Balboni; Valentina Onnis; Cenzo Congiu; Margherita Zotti; Yusuke Sasaki; Akihiro Ambo; Sharon D Bryant; Yunden Jinsmaa; Lawrence H Lazarus; Claudio Trapella; Severo Salvadori
Journal:  J Med Chem       Date:  2006-09-07       Impact factor: 7.446

2.  Peptidic delta opioid receptor agonists produce antidepressant-like effects in the forced swim test and regulate BDNF mRNA expression in rats.

Authors:  Mary M Torregrossa; Emily M Jutkiewicz; Henry I Mosberg; Gianfranco Balboni; Stanley J Watson; James H Woods
Journal:  Brain Res       Date:  2005-12-20       Impact factor: 3.252

3.  Dmt-Tic-NH-CH2-Bid (UFP-502), a potent DOP receptor agonist: in vitro and in vivo studies.

Authors:  Raffaella Vergura; Elena Valenti; Christopher P Hebbes; Elaine C Gavioli; Barbara Spagnolo; John McDonald; David G Lambert; Gianfranco Balboni; Severo Salvadori; Domenico Regoli; Girolamo Calo'
Journal:  Peptides       Date:  2006-09-11       Impact factor: 3.750

4.  Potent delta-opioid receptor agonists containing the Dmt-Tic pharmacophore.

Authors:  Gianfranco Balboni; Severo Salvadori; Remo Guerrini; Lucia Negri; Elisa Giannini; Yunden Jinsmaa; Sharon D Bryant; Lawrence H Lazarus
Journal:  J Med Chem       Date:  2002-12-05       Impact factor: 7.446

5.  Dermorphin gene sequence peptide with high affinity and selectivity for delta-opioid receptors.

Authors:  L H Lazarus; W E Wilson; R de Castiglione; A Guglietta
Journal:  J Biol Chem       Date:  1989-02-25       Impact factor: 5.157

6.  Endomorphin 2 analogues containing Dmp residue as an aromatic amino acid surrogate with high mu-opioid receptor affinity and selectivity.

Authors:  Yusuke Sasaki; Ai Sasaki; Hideko Niizuma; Harumi Goto; Akihiro Ambo
Journal:  Bioorg Med Chem       Date:  2003-03-06       Impact factor: 3.641

7.  Function of negative charge in the "address domain" of deltorphins.

Authors:  L H Lazarus; S Salvadori; V Santagada; R Tomatis; W E Wilson
Journal:  J Med Chem       Date:  1991-04       Impact factor: 7.446

8.  Some quantitative uses of drug antagonists.

Authors:  O ARUNLAKSHANA; H O SCHILD
Journal:  Br J Pharmacol Chemother       Date:  1959-03

9.  Kinetic parameters of narcotic agonists and antagonists, with particular reference to N-allylnoroxymorphone (naloxone).

Authors:  H W Kosterlitz; A J Watt
Journal:  Br J Pharmacol Chemother       Date:  1968-06

10.  Melatonin attenuates the development of antinociceptive tolerance to delta-, but not to mu-opioid receptor agonist in mice.

Authors:  Xu Dai; Shi-gang Cui; Shi-rong Li; Qiang Chen; Rui Wang
Journal:  Behav Brain Res       Date:  2007-05-01       Impact factor: 3.332
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  3 in total

1.  Role of 2',6'-dimethyl-l-tyrosine (Dmt) in some opioid lead compounds.

Authors:  Gianfranco Balboni; Erika Marzola; Yusuke Sasaki; Akihiro Ambo; Ewa D Marczak; Lawrence H Lazarus; Severo Salvadori
Journal:  Bioorg Med Chem       Date:  2010-06-25       Impact factor: 3.641

2.  Further studies on lead compounds containing the opioid pharmacophore Dmt-Tic.

Authors:  Gianfranco Balboni; Stella Fiorini; Anna Baldisserotto; Claudio Trapella; Yusuke Sasaki; Akihiro Ambo; Ewa D Marczak; Lawrence H Lazarus; Severo Salvadori
Journal:  J Med Chem       Date:  2008-08-05       Impact factor: 7.446

3.  Imidazolopiperazines: lead optimization of the second-generation antimalarial agents.

Authors:  Advait Nagle; Tao Wu; Kelli Kuhen; Kerstin Gagaring; Rachel Borboa; Caroline Francek; Zhong Chen; David Plouffe; Xuena Lin; Christopher Caldwell; Jared Ek; Suzanne Skolnik; Fenghua Liu; Jianling Wang; Jonathan Chang; Chun Li; Bo Liu; Thomas Hollenbeck; Tove Tuntland; John Isbell; Tiffany Chuan; Philip B Alper; Christoph Fischli; Reto Brun; Suresh B Lakshminarayana; Matthias Rottmann; Thierry T Diagana; Elizabeth A Winzeler; Richard Glynne; David C Tully; Arnab K Chatterjee
Journal:  J Med Chem       Date:  2012-04-23       Impact factor: 7.446
  3 in total

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