Target intelligence / Profile preview

Polyunsaturated fatty acid double bonds (PUFA double bonds)

Target
PUFA double bonds
Molecular classification
Lipid, Non-protein target, Polyunsaturated fatty acid (PUFA)
01

Overview

Reactive double bonds in membrane and plasma lipids, specifically those within polyunsaturated fatty acids (PUFAs), are critical chemical moieties that determine the structural and functional properties of biological membranes. These carbon-carbon double bonds, particularly at the bis-allylic positions, are highly susceptible to attack by reactive oxygen species (ROS), initiating a process known as lipid peroxidation (Yin et al., 2011, Chemical Reviews). This oxidative degradation is a hallmark of various pathologies, including atherosclerosis and neurodegenerative diseases, and is the execution mechanism for ferroptosis, a form of regulated cell death (Dixon et al., 2012, Cell). In therapeutic contexts, these double bonds are targeted by radical-trapping antioxidants like Vitamin E and experimental compounds like Ferrostatin-1, which protect the lipid bilayer from oxidative damage (Traber & Stevens, 2011, Free Radical Biology and Medicine). Conversely, medical ozone therapy utilizes the controlled reaction of ozone with these double bonds to generate lipid oxidation products that act as secondary messengers to modulate the immune system and antioxidant defenses (Bocci, 2006, "Ozone: A New Medical Drug"). Monitoring the integrity of these bonds is often achieved through biomarkers of lipid damage such as malondialdehyde and isoprostanes (Milne et al., 2005, Journal of Biological Chemistry).

Other names
Reactive lipid double bondsCarbon-carbon double bonds in lipidsBis-allylic C-H positionsUnsaturated fatty acid sitesLipid peroxidation sites
02

Mechanism of action

Radical-trapping antioxidant (RTA) activity to prevent lipid peroxidation chain reactions; Electrophilic addition reactions (in the case of ozone therapy); Inhibition of iron-dependent enzymatic or non-enzymatic oxidation of bis-allylic carbons.

03

Biological functions

Membrane fluidity regulationPrecursor for lipid signaling molecules (eicosanoids)Structural integrity of cellular membranesEnergy storageCellular signaling
04

Disease associations

AtherosclerosisNeurodegenerative diseaseIschemia-reperfusion injuryCancer (Ferroptosis)InflammationDiabetes mellitus
05

Safety considerations

Disruption of essential lipid signaling pathwaysPotential for pro-oxidant effects under specific conditionsAlteration of membrane permeability and transport protein functionDepletion of essential polyunsaturated fatty acids
06

Interacting drugs

Alpha-tocopherol (Vitamin E)

6 more in the full profile.

07

Biomarkers

Malondialdehyde (MDA)4-Hydroxynonenal (4-HNE)F2-isoprostanesOxidized low-density lipoprotein (oxLDL)C11-BODIPY fluorescence

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