Sulfo- and Oxy-analogues of Arginine: Synthesis, Analysis and Preliminary Biological Screening

Dzimbova, Tatyana; Miladinova, Elisaveta; Mohr, Stefan; Decheva, Roumyana; Balacheva, Aneliya A.; Schmid, Martin G.; Pajpanova, Tamara

doi:10.5562/cca1780

Cited by 5 publications

(2 citation statements)

References 12 publications

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“…Synthesis of unnatural amino acids sulfoarginine and norsulfoarginine was performed according to the previously published reaction procedure (Dzimbova et al, 2011(Dzimbova et al, , 2003. …”

Section: Amino Acids and Analoguesmentioning

confidence: 99%

MIF-1 and Tyr-MIF-1 analogues containing unnatural amino acids: synthesis, biological activity and docking studies

et al. 2014

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Melanocyte-inhibiting factor (MIF-1) is the first hypothalamic tripeptide which has been demonstrated to act not only in the brain but also in the pituitary. Tyr-MIF-1 acts as an opiate agonist. It binds selectively and with a high affinity to the l-opioid receptor when compared with the d-and jopioid receptors. A large number of analogues of MIF-1 and Tyr-MIF-1, containing various modifiers in their structures, have been synthesized and their analgesic effect was determined by various in vivo tests. The aim of current study was:(1) to synthesize new MIF-1 and Tyr-MIF-1 analogues containing sulfoarginine (sArg) and norsulfoarginine (NsArg) in the second and third position, respectively; (2) with the help of docking procedures to find the relationship between structure and biological activity of MIF-1 and Tyr-MIF-1 analogues previously synthesized and biologically tested; (3) using found correlation to predict the biological effect of newly synthesized analogues. New analogues of MIF-1 and Tyr-MIF-1 were synthesized using methods of peptide synthesis in solution. Docking was performed with GOLD 5.0 and a correlation between the obtained docking data and the values from in vivo test was found. Some structure-activity relationships were determined. According to the correlation, we made assumptions about the biological effect of sArg and NsArg containing MIF-1 and Tyr-MIF-1. A computational approach could be very useful in the elucidation of the structure-activity relationship and in the design of new analogues with desired biological effect.

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“…Synthesis of unnatural amino acids sulfoarginine and norsulfoarginine was performed according to the previously published reaction procedure (Dzimbova et al, 2011(Dzimbova et al, , 2003. …”

Section: Amino Acids and Analoguesmentioning

confidence: 99%

MIF-1 and Tyr-MIF-1 analogues containing unnatural amino acids: synthesis, biological activity and docking studies

et al. 2014

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“…The synthesis of sufoarginines and their hydrazides has been described previously (3,5). For the synthesis of the desired compounds, the sequence of reactions shown in synthetic scheme ( Fig.…”

Section: Methodsmentioning

confidence: 99%