Open AccessDeveloping Cyclic Opioid Analogues: Fluorescently Labeled Bioconjugates of Biphalin
Author(s) -
Azzurra Stefanucci,
Marilisa Pia Dimmito,
Gabriela Molnar,
John M. Streicher,
Ettore Novellino,
Gökhan Zengin,
Adriano Mollica
Publication year - 2020
Publication title -
acs medicinal chemistry letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.065
H-Index - 66
ISSN - 1948-5875
DOI - 10.1021/acsmedchemlett.9b00569
Subject(s) - chemistry , in vivo , peptidomimetic , fluorescence , cyclic peptide , combinatorial chemistry , opioid , in vitro , potency , maleimide , cysteine , receptor , biophysics , pharmacology , peptide , biochemistry , medicine , biology , enzyme , physics , microbiology and biotechnology , quantum mechanics , polymer chemistry
The development of bioconjugates is of pivotal importance in medicinal chemistry due to their potential applications as therapeutic agents to improve the targeting of specific diseases, decrease toxicity, or control drug release. In this work we achieved the synthesis and characterization of three novel opioid peptides fluorescently labeled, analogues of cyclic biphalin derivatives, namely 1D , 1C , and 2C . Among them, compound 1D , containing a dansyl-maleimide motif, exhibited an excellent binding affinity and functional potency for the δ-opioid receptor (DOR). 1D also demonstrated a strong fluorescence emission spectrum ranging from 300 to 700 nm. These features could be highly desirable for medical and biological applications needed for targeting the DOR, including in vivo imaging, and as a lead for the design of fluorescent probes.