Propentdyopents: Brief history of a family of dipyrrolic pigments

Research output: Contribution to journalReview article

Abstract

Propentdyopents are naturally occurring dipyrroles deriving from the metabolism of heme and characterized by a dipyrrin-1,9-dione motif. The unusual name propentdyopent is due to the first colorimetric method (the Stokvis reaction) for the detection of these compounds, which were initially isolated from urine samples. Upon reduction in alkaline solutions, they produced red species that were termed pentdyopents to describe with Greek numerals their absorption maximum (525 nm) in the visible range. The precursors to the red pentdyopents were thus indicated as propentdyopents.Over the course of several decades, these dipyrrolic compounds have appeared in several studies of human physiology, typically associated to conditions of abnormal heme metabolism and/or oxidative stress. Concurrently, synthetic investigations have confirmed their chemical structure, reactivity, and ability to coordinate metals as bidentate monoanionic ligands. Notably, the planar dipyrrindione platform can undergo reversible one-electron redox processes and thereby act as an electron reservoir in metal complexes. In combination with the documented ability of the carbonyl groups to act as hydrogen-bonding acceptors, the coordination chemistry of propentdyopents could lead to new applications for this old class of pigments. Furthermore, the observation of these pigments in several clinical contexts could potentially delineate a role of propentdyopents as diagnostic biomarkers. This mini-review summarizes both the chemistry and biology of propentdyopents while highlighting the ample space for new discoveries.

Original languageEnglish (US)
JournalJournal of Porphyrins and Phthalocyanines
DOIs
StateAccepted/In press - Jan 1 2019

Fingerprint

Heme
Metabolism
Pigments
Oxidative stress
Electrons
Coordination Complexes
Physiology
Biomarkers
Hydrogen bonds
Metals
Ligands
Oxidation-Reduction

Keywords

  • bilirubin degradation
  • dipyrrindione
  • electron reservoir
  • heme metabolism
  • redox-active ligand
  • urinary pigment

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Propentdyopents : Brief history of a family of dipyrrolic pigments. / Tomat, Elisa.

In: Journal of Porphyrins and Phthalocyanines, 01.01.2019.

Research output: Contribution to journalReview article

@article{2870598ff683458b97b4ca275edcbcb0,
title = "Propentdyopents: Brief history of a family of dipyrrolic pigments",
abstract = "Propentdyopents are naturally occurring dipyrroles deriving from the metabolism of heme and characterized by a dipyrrin-1,9-dione motif. The unusual name propentdyopent is due to the first colorimetric method (the Stokvis reaction) for the detection of these compounds, which were initially isolated from urine samples. Upon reduction in alkaline solutions, they produced red species that were termed pentdyopents to describe with Greek numerals their absorption maximum (525 nm) in the visible range. The precursors to the red pentdyopents were thus indicated as propentdyopents.Over the course of several decades, these dipyrrolic compounds have appeared in several studies of human physiology, typically associated to conditions of abnormal heme metabolism and/or oxidative stress. Concurrently, synthetic investigations have confirmed their chemical structure, reactivity, and ability to coordinate metals as bidentate monoanionic ligands. Notably, the planar dipyrrindione platform can undergo reversible one-electron redox processes and thereby act as an electron reservoir in metal complexes. In combination with the documented ability of the carbonyl groups to act as hydrogen-bonding acceptors, the coordination chemistry of propentdyopents could lead to new applications for this old class of pigments. Furthermore, the observation of these pigments in several clinical contexts could potentially delineate a role of propentdyopents as diagnostic biomarkers. This mini-review summarizes both the chemistry and biology of propentdyopents while highlighting the ample space for new discoveries.",
keywords = "bilirubin degradation, dipyrrindione, electron reservoir, heme metabolism, redox-active ligand, urinary pigment",
author = "Elisa Tomat",
year = "2019",
month = "1",
day = "1",
doi = "10.1142/S1088424619300210",
language = "English (US)",
journal = "Journal of Porphyrins and Phthalocyanines",
issn = "1088-4246",
publisher = "Society of Porphyrins and Phthalocyanines (SPP)",

}

TY - JOUR

T1 - Propentdyopents

T2 - Brief history of a family of dipyrrolic pigments

AU - Tomat, Elisa

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Propentdyopents are naturally occurring dipyrroles deriving from the metabolism of heme and characterized by a dipyrrin-1,9-dione motif. The unusual name propentdyopent is due to the first colorimetric method (the Stokvis reaction) for the detection of these compounds, which were initially isolated from urine samples. Upon reduction in alkaline solutions, they produced red species that were termed pentdyopents to describe with Greek numerals their absorption maximum (525 nm) in the visible range. The precursors to the red pentdyopents were thus indicated as propentdyopents.Over the course of several decades, these dipyrrolic compounds have appeared in several studies of human physiology, typically associated to conditions of abnormal heme metabolism and/or oxidative stress. Concurrently, synthetic investigations have confirmed their chemical structure, reactivity, and ability to coordinate metals as bidentate monoanionic ligands. Notably, the planar dipyrrindione platform can undergo reversible one-electron redox processes and thereby act as an electron reservoir in metal complexes. In combination with the documented ability of the carbonyl groups to act as hydrogen-bonding acceptors, the coordination chemistry of propentdyopents could lead to new applications for this old class of pigments. Furthermore, the observation of these pigments in several clinical contexts could potentially delineate a role of propentdyopents as diagnostic biomarkers. This mini-review summarizes both the chemistry and biology of propentdyopents while highlighting the ample space for new discoveries.

AB - Propentdyopents are naturally occurring dipyrroles deriving from the metabolism of heme and characterized by a dipyrrin-1,9-dione motif. The unusual name propentdyopent is due to the first colorimetric method (the Stokvis reaction) for the detection of these compounds, which were initially isolated from urine samples. Upon reduction in alkaline solutions, they produced red species that were termed pentdyopents to describe with Greek numerals their absorption maximum (525 nm) in the visible range. The precursors to the red pentdyopents were thus indicated as propentdyopents.Over the course of several decades, these dipyrrolic compounds have appeared in several studies of human physiology, typically associated to conditions of abnormal heme metabolism and/or oxidative stress. Concurrently, synthetic investigations have confirmed their chemical structure, reactivity, and ability to coordinate metals as bidentate monoanionic ligands. Notably, the planar dipyrrindione platform can undergo reversible one-electron redox processes and thereby act as an electron reservoir in metal complexes. In combination with the documented ability of the carbonyl groups to act as hydrogen-bonding acceptors, the coordination chemistry of propentdyopents could lead to new applications for this old class of pigments. Furthermore, the observation of these pigments in several clinical contexts could potentially delineate a role of propentdyopents as diagnostic biomarkers. This mini-review summarizes both the chemistry and biology of propentdyopents while highlighting the ample space for new discoveries.

KW - bilirubin degradation

KW - dipyrrindione

KW - electron reservoir

KW - heme metabolism

KW - redox-active ligand

KW - urinary pigment

UR - http://www.scopus.com/inward/record.url?scp=85075443435&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85075443435&partnerID=8YFLogxK

U2 - 10.1142/S1088424619300210

DO - 10.1142/S1088424619300210

M3 - Review article

AN - SCOPUS:85075443435

JO - Journal of Porphyrins and Phthalocyanines

JF - Journal of Porphyrins and Phthalocyanines

SN - 1088-4246

ER -