Norcystine, a New Tool for the Study of the Structure−Activity Relationship of Peptides

Samant, Manoj; Rivier, Jean

doi:10.1021/ol0606740

Cited by 13 publications

(31 citation statements)

References 35 publications

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“…The racemic BocNcy(aryl/alkyl)-OH (4a-c) were converted into their methyl esters (5a-c) and then resolved by enzymatic hydrolysis with papain. 15 The enantiomeric excess of the resolved amino acids (6a-c) was found to be greater than 98% according to chiral HPLC.…”

Section: Chemistrymentioning

confidence: 95%

Structure−Activity Relationship Studies of Gonadotropin-Releasing Hormone Antagonists ContainingS-Aryl/Alkyl Norcysteines and Their Oxidized Derivatives

et al. 2007

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A series of acyline analogues incorporating L-and D-isomers of S-arylated/alkylated norcysteines [Ncy(R), where R is 2-naphthyl, methyl and isopropyl] at positions 1, 4, 7 and 10 were synthesized. Some of these analogues were mono-and di-oxidized to sulfoxides and sulfones. All of the analogues of acyline were screened for the antagonism of GnRH-induced response in a reporter gene assay in HEK-293 cells expressing the human GnRH receptor. Nine of the analogues (9, 11, 15, 16, 17, 19, 20, 21, and 22) had an antagonist potency (IC 50 < 2 nM) similar to that of acyline (IC 50 = 0.52 nM) in this assay. Selected analogues (9, 11, 15, 16, 19 and 21) were tested in vitro for their antagonism at the rat GnRH-R in a reporter gene assay as well as in an in vivo intact male rat assay. Analogues 9 and 15 were most potent in suppressing testosterone levels.

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Section: Chemistrymentioning

confidence: 95%

Structure−Activity Relationship Studies of Gonadotropin-Releasing Hormone Antagonists ContainingS-Aryl/Alkyl Norcysteines and Their Oxidized Derivatives

et al. 2007

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“…Boc-Ncy(Mob)-OH, Boc-D/L-Ncy(Mob)-OH, 6 Boc-Hcy(Mob)-OH and BocDHcy(Mob)-OH were synthesized in our laboratory. 7 The peptides were cleaved and fully deprotected with hydrogen fluoride.…”

Section: Peptide Synthesismentioning

confidence: 99%

“…NMR samples were prepared by dissolving 2 mg of the analogue in 0.5 mL of DMSO-d 6 . The 1 H NMR spectra were recorded on a Bruker 700 MHz spectrometer operating at proton frequency of 700 MHz.…”

Section: Nmr Studiesmentioning

confidence: 99%

Ring Size in Octreotide Amide Modulates Differently Agonist versus Antagonist Binding Affinity and Selectivity

et al. 2008

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“…This antagonist blocks GnRH and inhibits LH production, which in turn causes a suppression of testosterone and DHT [41,68]. In addition, other antagonistic peptide analogues such as Antide [N-Ac-DNal 1 , DpClPhe 2 , DPal 3 , Lys(Nic) 5 , DLys(Nic) 6 , Lys(iPr) 8 Rivier et al have designed and synthesized a large number of modified GnRH analogues, both agonistic [69] and antagonistic [70][71][72][73], using unnatural amino acids [74,75], cyclization and in some cases dicyclization [76][77][78][79]. Variable substitutions were involved in almost all positions, especially in the N-terminal, leading to the synthesis of antagonists [80][81][82].…”

Section: Nhmentioning

confidence: 99%

Peptides as Therapeutic Agents or Drug Leads for Autoimmune, Hormone Dependent and Cardiovascular Diseases

Mantzourani¹,

Laimou²,

Matsoukas³

et al. 2008

AIAAMC

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Peptides regulate most physiological processes, mainly by binding to specific receptors located on the cell surface and inducing a series of signals, neurotransmissions or the release of growth factors. There has been a rapid expansion in the use of peptides as therapeutic agents after the 1960s, but a series of unfortunate side effects present in Phase I and II clinical studies combined with their low bioavailability, led to the introduction of the idea of peptidomimetics as alternative compounds that mimic the biological activity of peptides, while offering the advantages of increased bioavailability, biostability, bioefficiency, and bioselectivity. Since then new peptides with promising in vitro results, involving the monoclonal antibody expansion, as well as the newly launched research field for novel formulations for increasing peptides' bioavailability, redirected the interest on the peptide market. In this report we will highlight three areas where the use of peptides has shown promising results, with products that are either currently used as drugs or included into Phase III clinical studies.

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Norcystine, a New Tool for the Study of the Structure−Activity Relationship of Peptides

Cited by 13 publications

References 35 publications

Structure−Activity Relationship Studies of Gonadotropin-Releasing Hormone Antagonists ContainingS-Aryl/Alkyl Norcysteines and Their Oxidized Derivatives

Structure−Activity Relationship Studies of Gonadotropin-Releasing Hormone Antagonists ContainingS-Aryl/Alkyl Norcysteines and Their Oxidized Derivatives

Ring Size in Octreotide Amide Modulates Differently Agonist versus Antagonist Binding Affinity and Selectivity

Peptides as Therapeutic Agents or Drug Leads for Autoimmune, Hormone Dependent and Cardiovascular Diseases

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