Synthesis and biological activity of new series of N-modified analogues of the N/OFQ(1–13)NH2 with aminophosphonate moiety

New series of N-modified analogues of the N/OFQ(1–13)NH 2 with aminophosphonate moiety have been synthesized and investigated for biological activity. These peptides were prepared by solid-phase peptide synthesis—Fmoc-strategy. The N/OFQ(1–13)NH 2 analogues were tested for agonistic activity in vitr...

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Bibliographic Details
Published in:Amino acids 2012-09, Vol.43 (3), p.1217-1223
Main Authors: Todorov, Petar T., Mateeva, Polina I., Zamfirova, Rositza N., Pavlov, Nikola D., Naydenova, Emilia D.
Format: Article
Language:English
Subjects:
Amino Acid Sequence
Analytical Chemistry
Animals
Biochemical Engineering
Biochemistry
Biomedical and Life Sciences
Electric Stimulation
In Vitro Techniques
Life Sciences
Male
Muscle Contraction - drug effects
Muscle, Smooth - drug effects
Muscle, Smooth - physiology
Neurobiology
Nociceptin
Nociceptin Receptor
Opioid Peptides - chemical synthesis
Opioid Peptides - pharmacology
Organophosphonates - chemical synthesis
Organophosphonates - pharmacology
Original Article
Peptide Fragments - chemical synthesis
Peptide Fragments - pharmacology
Proteomics
Rats
Rats, Wistar
Receptors, Opioid - agonists
Structure-Activity Relationship
Vas Deferens - drug effects
Vas Deferens - physiology
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Summary:New series of N-modified analogues of the N/OFQ(1–13)NH 2 with aminophosphonate moiety have been synthesized and investigated for biological activity. These peptides were prepared by solid-phase peptide synthesis—Fmoc-strategy. The N/OFQ(1–13)NH 2 analogues were tested for agonistic activity in vitro on electrically stimulated rat vas deferens smooth-muscle preparations isolated from Wistar albino rats. Our study has shown that the selectivity of the peptides containing 1-[(methoxyphosphono)methylamino]cycloalkanecarboxylic acids to the N-side of Phe is not changed—they remain selective agonists of NOP receptors. The derivative with the largest ring ( NOC-6 ) demonstrated efficacy similar to that of N/OFQ(1–13)NH 2 , but in a 10-fold higher concentration. The agonistic activity of newly synthesized N-modified analogues of N/OFQ(1–13)NH 2 with aminophosphonate moiety was investigated for the first time.
ISSN:0939-4451
1438-2199
DOI:10.1007/s00726-011-1177-7