Cobalt(III)- and rhodium(III)-porphyrin complexes for the effective degradation of fentanyl: Biological inactivation and mechanistic insights

Hemant Pal; Anneli Nina; Okhil K Nag; Christopher D Chouinard; Amanda Pitt; Gregory A Ellis; Scott A Walper; Jeffrey Deschamps; Aurora Burkus-Matesevac; Kathy Maiello; James B Delehanty; D Andrew Knight

doi:10.1016/j.jinorgbio.2022.111935

Cobalt(III)- and rhodium(III)-porphyrin complexes for the effective degradation of fentanyl: Biological inactivation and mechanistic insights

J Inorg Biochem. 2022 Oct:235:111935. doi: 10.1016/j.jinorgbio.2022.111935. Epub 2022 Jul 18.

Affiliations

¹ Department of Biomolecular and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32922, USA.
² Center for Bio/Molecular Science and Engineering, US Naval Research Laboratory, 4555 Overlook Avenue, SW, Washington, DC 20375, USA.
³ Center for Bio/Molecular Science and Engineering, US Naval Research Laboratory, 4555 Overlook Avenue, SW, Washington, DC 20375, USA. Electronic address: james.delehanty@nrl.navy.mil.
⁴ Department of Biomolecular and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32922, USA. Electronic address: aknight@fit.edu.

PMID: 35932757
DOI: 10.1016/j.jinorgbio.2022.111935

Abstract

Cobalt(III) and rhodium(III) complexes containing the water-soluble porphyrin ligand meso-tri(4-sulfonatophenyl)mono(4-carboxyphenyl)porphine (C₁S₃TPP), [Rh(C₁S₃TPP)]Na_x•nH₂O (1) and [Co(C₁S₃TPP)]Na_x•nH₂O (2) were prepared from the direct reaction of free porphyrin and metal chloride salts in refluxing MeOH/DMF or EtOH/H₂O. Compounds 1 and 2 were characterized using UV-vis and ¹H NMR spectroscopies, and high-resolution mass spectrometry. Cell culture based assays of opioid receptor activation showed that while the rhodium complex reduced fentanyl opioid activity 113-fold to an IC50 value of 1.7 μM, the cobalt complex reduced fentanyl activity by 160-fold to an IC50 value of 2.4 μM. An oxidative mechanism for fentanyl breakdown is proposed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cobalt / chemistry
Fentanyl / pharmacology
Ligands
Porphyrins* / chemistry
Porphyrins* / pharmacology
Rhodium* / chemistry

Substances

Ligands
Porphyrins
Cobalt
Rhodium
Fentanyl