Cyclic Opioid Peptides

Curr Med Chem. 2016;23(13):1288-303. doi: 10.2174/0929867323666160427123005.

Abstract

For decades the opioid receptors have been an attractive therapeutic target for the treatment of pain. Since the first discovery of enkephalin, approximately a dozen endogenous opioid peptides have been known to produce opioid activity and analgesia, but their therapeutics have been limited mainly due to low blood brain barrier penetration and poor resistance to proteolytic degradation. One versatile approach to overcome these drawbacks is the cyclization of linear peptides to cyclic peptides with constrained topographical structure. Compared to their linear parents, cyclic analogs exhibit better metabolic stability, lower offtarget toxicity, and improved bioavailability. Extensive structure-activity relationship studies have uncovered promising compounds for the treatment of pain as well as further elucidate structural elements required for selective opioid receptor activity. The benefits that come with employing cyclization can be further enhanced through the generation of polycyclic derivatives. Opioid ligands generally have a short peptide chain and thus the realm of polycyclic peptides has yet to be explored. In this review, a brief history of designing ligands for the opioid receptors, including classic linear and cyclic ligands, is discussed along with recent approaches and successes of cyclic peptide ligands for the receptors. Various scaffolds and approaches to improve bioavailability are elaborated and concluded with a discourse towards polycyclic peptides.

Publication types

  • Review

MeSH terms

  • Animals
  • Humans
  • Opioid Peptides / pharmacology*
  • Pain / drug therapy*
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / pharmacology*
  • Receptors, Opioid / agonists*

Substances

  • Opioid Peptides
  • Peptides, Cyclic
  • Receptors, Opioid