Quinone Moiety Research Articles

Design, Synthesis, Physicochemical Properties, and Biological Activity of Thymidine Compounds Attached to 5,8-Quinolinedione Derivatives as Potent DT-Diaphorase Substrates.

After heart disease, cancer is the second-leading cause of death worldwide. The most effective method of cancer treatment is target therapy. One of the potential goals of therapy could be DT-diaphorase, which reduces quinone moiety to hydroquinone, and reactive oxygen species are create as a byproduct. The obtaining of hybrid compounds containing the quinone moiety and other bioactive compounds leads to new derivatives which can activate DT-diaphorase. The aim of this research was the synthesis and characterization of new hybrids of 5,8-quinolinedione with thymidine derivatives. The analysis of the physicochemical properties shows a strong relationship between the structure and properties of the tested compounds. The enzymatic assay shows that hybrids are good substrates of NQO1 protein. The analysis of the structure-activity relationship shows that the localization of nitrogen atoms influences the enzymatic conversion rate. The analysis was supplemented by a molecular docking study. Comparing the results of the enzymatic assay and the molecular docking presents a strong correlation between the enzymatic conversion rate and the scoring value.

The Study of Reaction of Hexafluoro‐1,4‐Napthoquinone With Substituted 5‐Aminopyrazoles

ABSTRACTFor the first time, the interaction of perfluoro‐1,4‐naphthoquinone with various 5‐aminopyrazoles was investigated. It was shown that three types of products can be obtained depending on the structure of starting aminopyrazole. For all examples, the substitution of one fluorine atom in quinone moiety was observed. Wherein, in most cases, the starting aminopyrazoles act as a C‐nucleophile leading to 2‐(5‐aminopyrazol‐4‐yl)‐3,5,6,7,8‐pentafluoronaphthalene‐1,4‐diones. At the same time substrates unsubstituted at ring nitrogen atom regiospecifically react at aminogroup resulting in the formation of 2,5,6,7,8‐pentafluoro‐3‐((pyrazol‐5‐yl)amino)naphthalene‐1,4‐diones. Besides that, the absence of steric hindrance in the pyrazole unit allowed us to direct the process at nitrogen atom in Position 2 and synthesize zwitter‐ionic 3‐(5‐aminopyrazol‐2‐ium‐2‐yl)‐5,6,7,8‐tetrafluoro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐olates. The structures of two types of obtained products were confirmed by x‐ray analysis.

Electrochemistry of Diquinonyl Amines with an Internal Proton Source

It is well established that quinones play an important role in various biological systems. Studying electrochemical properties of quinones affords fundamental knowledge of semi-quinone radicals formation in vivo and in vitro in different media.Following our previous work on electrochemical properties of various quinonyl amines [1], Scheme 1 below describes seven diquinonyl amines. Noteworthy that six of them (1-6) contain an internal proton donor (‘NH’) except for the seventh one (7), in which both quinone moieties are attached to ‘NMe’ group. Their redox potentials were measured by cyclic voltammetry in dichloromethane [2].The results show a strong dependence of the nature of substituent on the first reduction potentials, and that protonation of diquinonyl amines is feasible by internal proton source even in a non-polar medium.

Immobilization of PCET Materials for Electrochemical pH Swing Driven Carbon Capture

Proton-coupled electron transfer (PCET) is a promising method in the realm of carbon capture and release mechanisms. Its fundamental capacity lies in electrochemically inducing pH swings within an aqueous solution, leveraging the high solubility of carbonates in highly alkaline water to capture CO2 and subsequently release iton demand when the aqueous solution is acidified. PCET-based methods promise higher energy efficiency for carbon capture compared to other electrochemical carbon capture methods because they feature fast charge transfer kinetics and can decouple gas-liquid contact and electrochemical activation. In theory, they also allow the use of cheap, widely available small-molecule PCET agents. However, in practice, PCET agents have shown a key limitation that has, thus far, hindered their scalability: oxygen-induced chemical degradation with continued electrochemical cycling. In this work we mitigate the prevailing issue of oxygen sensitivity by immobilizing PCET agents onto a fabric substrate. Via reactive vapor deposition (RVD), porous and conductive films composed of PEDOT-Cl and poly-aminoanthroquinone (PAAQ) are deposited on the surface of a wool felt blend fabric. This approach resulted in the development of a cost-effective, metal-free, and efficient electrode for both capture and release of CO2. Through electrochemical evaluation, the performance of PCET-active quinone moieties present on PAAQ was measured. The overall efficiency of electrochemical capture from gaseous CO2 was found to be 197 kJ/molCO2, substantiating the efficacy of this novel electrode. This work highlights the potential of fabric-immobilized PCET agents and presents a promising avenue towards a sustainable, efficient, and economically viable approach to carbon capture and release technologies.

Molecular Weights of Dissolved Organic Matter Significantly Affect Photoaging of Microplastics.

The fate of ubiquitous microplastics (MPs) is largely influenced by dissolved organic matter (DOM) in aquatic environments, which has garnered significant attention. The reactivity of DOM is reported to be greatly regulated by molecular weights (MWs), yet little is known about the effects of different MW DOM on MP aging. Here, the aging behavior of polystyrene MPs (PSMPs) in the presence of different MW fulvic acids (FAs) and humic acids (HAs) was systematically investigated. Under ultraviolet (UV) illumination, O/C of PSMPs aged for 96 h surged from 0.008 to 0.146 in the lower MW FA (FA<1kDa) treatment, suggesting significant PSMP aging. However, FA exhibited a stronger effect on facilitating PSMP photoaging than HA, which can be attributed to the fact that FA<1kDa contains more quinone and phenolic moieties, demonstrating a higher redox capacity. Meanwhile, compared to other fractions, FA<1kDa was more actively involved in the increase of different reactive species yields by 50-290%, including •OH, which plays a key role in PSMP photoaging, and contributed to a 25% increase in electron-donating capacity (EDC). This study lays a theoretical foundation for a better understanding of the environmental fate of MPs.

Site-selective peptide bond hydrolysis and ligation in water by short peptide-based assemblies

The evolution of complex chemical inventory from Darwin's nutrient-rich warm pond necessitated rudimentary yet efficient catalytic folds. Short peptides and their self-organized microstructures, ranging from spherical colloids to amyloidogenic aggregates might have played a crucial role in the emergence of contemporary catalytic entities. However, the question of how short peptide fragments had functions akin to contemporary complex enzymes to catalyze cleavage and formation of highly stable peptide bonds that constitute the backbone of all proteins remains an unresolved yet fundamentally important question in terms of the origins of enzymes. We report short-peptide-based spherical assemblies that demonstrated residue-specific cleavage and formation of peptide bonds of diverse peptide-based substrates under aqueous environment. Despite the short sequence length, the assemblies utilized the synergistic collaboration of four residues which included the catalytic triad of extant serine proteases with a nonproteinogenic amino acid (quinone moiety), to facilitate proteolysis, ligation, and a three-step (hydrolysis-ligation-hydrolysis) cascade. Such short-peptide-based catalytic assemblies argue for their candidacy as the earliest protein folds and open up avenues for biotechnological applications.

Location and interaction of idebenone and mitoquinone in a membrane similar to the inner mitochondrial membrane. Comparison with ubiquinone 10

Oxygen is essential for aerobic life on earth but it is also the origin of harmful reactive oxygen species (ROS). Ubiquinone is par excellence the endogenous cellular antioxidant, but a very hydrophobic one. Because of that, other molecules have been envisaged, such as idebenone (IDE) and mitoquinone (MTQ), molecules having the same redox active benzoquinone moiety but higher solubility. We have used molecular dynamics to determine the location and interaction of these molecules, both in their oxidized and reduced forms, with membrane lipids in a membrane similar to that of the mitochondria. Both IDE and reduced IDE (IDOL) are situated near the membrane interface, whereas both MTQ and reduced MTQ (MTQOL) locate in a position adjacent to the phospholipid hydrocarbon chains. The quinone moieties of both ubiquinone 10 (UQ10) and reduced UQ10 (UQOL10) in contraposition to the same moieties of IDE, IDOL, MTQ and MTQOL, located near the membrane interphase, whereas the isoprenoid chains remained at the middle of the hydrocarbon chains. These molecules do not aggregate and their functional quinone moieties are located in the membrane at different depths but near the hydrophobic phospholipid chains whereby protecting them from ROS harmful effects.

Towards Immobilized Proton-Coupled Electron Transfer Agents for Electrochemical Carbon Capture from Air and Seawater

Electrochemical CO2 separation has drawn attention as a promising strategy for using renewable energy to mitigate climate change. Redox-active compounds that undergo proton-coupled electron transfer (PCET) are an impetus for pH-swing-driven CO2 capture at low energetic costs. However, multiple barriers hinder this technology from maturing, including sensitivity to oxygen and the slow kinetics of CO2 capture. Here, we use vapor phase chemistry to construct a textile electrode comprising an immobilized PCET agent, poly(1-aminoanthraquinone) (PAAQ), and incorporate it into redox flow cells. This design contrasts with others that use dissolved PCET agents by confining proton-storage to the surface of an electrode kept separate from an aqueous, CO2-capturing phase. This system facilitates carbon capture from gaseous sources (a 1% CO2 feed and air), as well as seawater, with the latter at an energetic cost of 202 kJ/molCO2, and we find that quinone moieties embedded within the electrode are more stable to oxygen than dissolved counterparts. Simulations using a 1D reaction-transport model show that moderate energetic costs should be possible for air capture of CO2 with higher loadings of polymer-bound PCET moieties. The remarkable stability of this system sets the stage for producing textile-based electrodes that facilitate pH-swing-driven carbon capture in practical situations.

Synthesis of chlorophyll–quinone conjugates by Diels–Alder reaction and their fluorescence quenching by intramolecular electron transfer

Methyl pyropheophorbides-a possessing a 1,4-naphthoquinon-5-yl or 9,10-anthraquinon-1-yl group at the 3-position were prepared by the Diels–Alder reaction of 3-(1,3-butadienyl)chlorin with benzoquinone or naphthoquinone and successive dehydrogenative oxidation. The synthetic chlorophyll-a derivatives directly bonded with the quinone were atropisomers around the C3–C31 bond, which were readily separated by HPLC. Since the quinone moiety was nearly perpendicular to the chlorin π-system, the distance and orientation between the chlorin and quinone chromophores were fixed in a molecule. The visible absorption spectra of the synthetic chlorin–quinone conjugates were independent of the quinone part and the axial chirality. Their fluorescence emissions were almost completely quenched by intramolecular electron transfer from the photoexcited chlorin to the quinone, which resembled the charge-separating process in photosynthetic reaction centers.

Methane emissions and the microbial community in flooded paddies affected by the application of Fe-stabilized natural organic matter

Redox chemistry involving the quinone/phenol cycling of natural organic matter (NOM) is known to modulate microbial respiration. Complexation with metals or minerals can also affect NOM solubilization and stability. Inspired by these natural phenomena, a new soil amendment approach was suggested to effectively decrease methane emissions in flooded rice paddies. Structurally stable forms of NOM such as lignin and humic acids (HAs) were shown to decrease methane gas emissions in a vial experiment using different soil types and rice straw as a methanogenic substrate, and this inhibitory behavior was likely enhanced by ferric ion–NOM complexation. A mechanistic study using HAs revealed that complexation facilitated the slow release of the humic components. Interestingly, borohydride-based reduction, which transformed quinone moieties into phenols, caused the HAs to lose their inhibitory capacity, suggesting that the electron-accepting ability of HAs is vital for their inhibitory effect. In rice field tests, the humic–metal complexes were shown to successfully mitigate methane generation, while carbon dioxide emissions were relatively unchanged. Microbial community analysis of the rice fields by season revealed a decrease in specific cellulose-metabolizing and methanogenic genera associated with methane emissions. In contrast, the relative abundance of Thaumarchaeota and Actinomycetota, which are associated with NOM and recalcitrant organics, was higher in the presence of Fe-stabilized HAs. These microbial dynamics suggest that the slow release of humic components is effective in modulating the anoxic soil microbiome, possibly due to their electron-accepting ability. Given the simplicity, cost-effectiveness, and soil-friendly nature of complexation processes, Fe-stabilized NOM represents a promising approach for the mitigation of methane emissions from flooded rice paddies.

Morphology and size control of an amorphous conjugated polymer network containing quinone and pyrrole moieties via precipitation polymerization.

Morphology and size control of insoluble and infusible conjugated polymers are significant for their applications. Development of a precipitation polymerization route without using a surface stabilizer is preferred to control the reaction, morphology, and size. In the present work, precipitation polymerization for an amorphous conjugated polymer network, a new type of polymerized structure containing functional units, was studied for the size and morphology control in the solution phase at low temperature. The random copolymerization of benzoquinone (BQ) and pyrrole (Py) monomers formed microspheres of the BQ-Py network polymers as the precipitates in the solution phase. The particle diameter was controlled in the range of 70 nm and 1 μm by changing the pH of the solution and concentration of the monomers. The resultant nanoparticles were applied to a metal-free electrocatalyst for the hydrogen evolution reaction (HER). The catalytic activity of the BQ-Py nanoparticles was higher than that of the bulk micrometer-sized particles. The results imply that the morphology and size of amorphous conjugated polymer networks can be controlled by precipitation polymerization.

A family of dioxyarylene linked di-o-quinones. Structural dependence on the topology of the linker: a comparative study

The intramolecular exchange interaction between paramagnetic centers in the biradical dianion derivatives of di-o-quinones depends on the steric environment of the linker connecting quinone moieties, the topology of the linker plays a secondary role.

Humic substances as electron acceptor for anaerobic oxidation of methane (AOM) and electron shuttle in Mn (IV)-dependent AOM

Anaerobic methanotrophic archaea (ANME) belonging to the family Methanoperedenaceae are crucial for the global carbon cycle and different biogeochemical processes, owing to their metabolic versatility to couple anaerobic oxidation of methane (AOM) with different electron acceptors. A universal feature of Methanoperedenaceae is the abundant genes encoded in their genomes associated with extracellular electron transfer (EET) pathways. Candidatus. ‘Methanoperedens manganicus’, an archaeon belonging to the family Methanoperedenaceae, was recently enriched in a bioreactor performing AOM coupled with Mn (IV) reduction. Using this EET-capable ANME, we tested the hypothesis in this study that ANME can catalyse the humic-dependent AOM for growth. A two-year incubation showed that AOM activity can be sustained by Ca. ‘M. manganicus’ consortium in a bioreactor fed only with humic acids and methane. An isotopic mass balance batch test confirmed that the observed AOM was coupled to the reduction of humic acids. The increase of relative abundance of Ca. ‘M. manganicus’, and the total archaea population in the microbial community suggested that Ca. ‘M. manganicus’ can grow on methane and humic acids. The observation of humic-dependent AOM led to a subsequent hypothesis that humic acids could be used as the electron shuttle to mediate the EET in dissimilatory Mn (IV) reduction by Ca. ‘M. manganicus’. We tested this hypothesis by adding humic acids to a Ca. ‘M. manganicus’ dominated-culture, which showed that the AOM rate was doubled by the addition of humic acids. X-ray photoelectron spectroscopy (XPS) showed that quinone moieties were consumed when humic acids worked as electron acceptors while remaining stable when functioning as a shuttle for electron transfer. The results of our study suggest that humic acids may serve as electron shuttles to allow ANME to access more electron acceptors through long-range EET.

How a natural antibiotic uses oxidative stress to kill oxidant-resistant bacteria.

Natural products that possess antibiotic and antitumor qualities are often suspected of working through oxidative mechanisms. In this study, two quinone-based small molecules were compared. Menadione, a classic redox-cycling compound, was confirmed to generate high levels of reactive oxygen species inside Escherichia coli. It inactivated iron-cofactored enzymes and blocked growth. However, despite the substantial levels of oxidants that it produced, it was unable to generate significant DNA damage and was not lethal. Streptonigrin, in contrast, was poorer at redox cycling and did not inactivate enzymes or block growth; however, even in low doses, it damaged DNA and killed cells. Its activity required iron and oxygen, and in vitro experiments indicated that its quinone moiety transferred electrons through the adjacent iron atom to oxygen. Additionally, in vitro experiments revealed that streptonigrin was able to damage DNA without inhibition by catalase, indicating that hydrogen peroxide was not involved. We infer that streptonigrin can reduce bound oxygen directly to a ferryl species, which then oxidizes the adjacent DNA, without release of superoxide or hydrogen peroxide intermediates. This scheme allows streptonigrin to kill a bacterial cell without interference by scavenging enzymes. Moreover, its minimal redox-cycling behavior avoids alerting either the OxyR or the SoxRS systems, which otherwise would block killing. This example highlights qualities that may be important in the design of oxidative drugs. These results also cast doubt on proposals that bacteria can be killed by stressors that merely stimulate intracellular O2- and H2O2 formation.

Spectral Heterogeneity of Phenol Blue in Protic Solvents Revealed by Ultrafast Nonradiative Decay Dynamics

AbstractPhenol blue (PhB) is a dye that exhibits positive solvatochromism which is also nonfluorescent due to its ultrashort excited state lifetime. We have conducted femtosecond time‐resolved transient absorption (TA) spectroscopic measurements of a PhB solution using two distinct excitation wavelengths, at shorter and longer wavelength sides of the visible absorption band. The results revealed that a long‐lived heterogeneity exists in protic solvents whereas, in aprotic solvents, the system rapidly returns to the original thermal equilibrium on the ultrafast timescale. Interestingly, the lifetime of the heterogeneity is longer for methanol (MeOH) compared to ethanol (EtOH) solution suggesting stronger interaction between PhB and MeOH. Additionally, since the excited state lifetime of PhB was still in the sub‐picosecond domain even in a polymer matrix, we suggest a nonradiative decay mechanism through high‐frequency vibrational modes without involving large structural reconfiguration such as twisting of the benzoquinone (BzQ) moiety.

Tunable Supramolecular Ag+-Host Interactions in Pillar[n]arene[m]quinones and Ensuing Specific Binding to 1-Alkynes.

We developed an improved, robust synthesis of a series of pillar[6]arenes with a varying number (0-3) of quinone moieties in the ring. This easy-to-control variation yielded a gradually less electron-rich cavity in going from zero to three quinone units, as shown from the strength of host-guest interactions with silver ions. Such macrocycle-Ag2 complexes themselves were shown to display an unprecedented, sharp distinction between terminal alkynes, which strongly bound to such complexes, and internal alkynes, internal alkenes and terminal alkenes, which do hardly bind.

Analysis of Quinolinequinone Analogs with Promising Cytotoxic Activity against Breast Cancer.

It is quite challenging to find out bioactive molecules in the vast chemical universe. Quinone moiety is a unique structure with a variety of biological properties, particularly in the treatment of cancer. In an effort to develop potent and secure antiproliferative lead compounds, five quinolinequinones (AQQ1-5) described previously have been selected and submitted to the National Cancer Institute (NCI) of Bethesda to envisage their antiproliferative profile based on the NCI Developmental Therapeutics Program. According to the preliminary in vitro single-dose anticancer screening, four of five quinolinequinones (AQQ2-5) were selected for five-dose screening and they displayed promising antiproliferative effects against several cancer types. All AQQs showed a excellent anticancer profile with low micromolar GI50 and TGI values against all leukemia cell lines, some non-small cell lung and ovarian cancer, most colon, melanoma, and renal cancer, and in addition to some breast cancer cell lines. AQQ2-5 reduced the proliferation of all leukemia cell lines at a single dose and five additional doses, as well as some non-small cell lung and ovarian cancer, the majority of colon cancer, melanoma and renal cancer, and some breast cancer cell lines. This motivated us to use in vitro, in silico, and in vivo technologies to further investigate their mode of action. We investigated the in vitro cytotoxic activities of the most promising compounds, AQQ2 and AQQ3, in HCT-116 colon cancer, MCF7 and T-47D breast cancer, and DU-145 prostate cancer cell lines, and HaCaT human keratinocytes. Concomitantly, IC50 values of AQQ2 and AAQ3 against MCF7 and T-47D cell lines of breast cancer, DU-145 cell lines of prostate cancer, HCT-116 cell lines of colon cancer, and HaCaT human keratinocytes were determined. AQQ2 exhibited anticancer activity through the induction of apoptosis and caused alterations in the cell cycle. In silico pharmacokinetic studies of all analogs have been carried out against ATR, CHK1, WEE1, CDK1, and CDK2. In addition to this, in vitro ADME and in vivo pharmacokinetic profiling for the most effective AAQ (AAQ2) have been studied.

The microbial oxidation of pharmaceuticals in an anaerobic aqueous environment: Effect of dissolved organic matter fractions from different sources

Previous studies have demonstrated the importance of dissolved organic matter (DOM) on the biodegradation of trace organic contaminants occurred in the hyporheic zone. However, the role of diverse DOM fractions with distinct physicochemical properties on the biodegradation of pharmaceuticals under reducing conditions is scarcely known. To address this knowledge gap, DOMs derived from road-deposited sediment, soil, and active sludge (namely allochthonous DOM) and algae (namely autochthonous DOM) were collected and isolated into different fractions. Thereafter, the effect of DOM fractions on the anaerobic microbial oxidation of two typical pharmaceuticals, i.e., ritonavir (RTV) and tetracycline (TC) was explored by using simulated anaerobic microcosms. Mechanistic insights into how DOM fractions from different sources influence pharmaceutical biodegradation processes were provided by optical and electrochemical analyses. Results showed that humic acid and fulvic acid fractions from allochthonous DOM could enhance the biodegradation of TC (12.2 % per mgC/L) and RTV (14.5 % per mgC/L), while no significant impact was observed for that of hydrophilic fractions. However, autochthonous DOM promoted the biodegradation of TC (4.17 % per mgC/L) and inhibited that of RTV. Mechanistic analysis showed that the higher of humification and aromatization level of DOM components, the stronger their promotive effect on the biodegradation of TC and RTV. Further, the promotive mechanism could be attributed to the response of quinone moieties in DOM as extracellular electron acceptors that yields more energy to support microbial metabolism. These results provide a more comprehensive understanding of diverse DOM fractions mediating microbial anaerobic oxidation of trace organic pollutants, and extend our insights into contamination control and remediation technologies.

Dimerizing Lawsone into Bis-lawsone to Counter Solubility and Attain Facile Zn2+ Ion Diffusion for Stable Capacity in Aqueous Zinc-Ion Batteries

Given the higher volumetric capacity of Zn (5853 mAh cm−3), aqueous zinc-ion batteries can be considered as alternatives to lithium-ion batteries for energy storage applications. Here we focus on redox-active, non-toxic, and eco-friendly organic materials with quinone moiety, i.e., Lawsone (LS) and its dimer Bis-lawsone (BL), as a cathode material for Zn-ion batteries. The reversibility of LS and BL is confirmed by cyclic voltammetry between 0.3 and 1.6 V in zinc sulfate and zinc triflate electrolytes. The electrochemical performance of BL in the zinc triflate electrolyte is improved by the reduction in the solubility of BL in the electrolyte and improvement in Zn2+ diffusion in the BL matrix. Besides, it is known that Zn electrodes passivate better in zinc triflates, which contributes to improved plating/stripping of Zn. The dimerization strategy counteracts solubility and facilitates the diffusion of Zn2+, resulting in a stable charge–discharge with a specific capacity of 200 mAh g–1. The cell attained 77% of the theoretical capacity at a current density of 100 mA g–1. Zn-BL cells show fast kinetics and reversibility for up to 760 cycles retaining 85% of initial capacity despite the partial solubility of BL in electrolytes. In addition, the Nafion-212 membrane is introduced as a separator instead of a traditional glass fiber separator. The negatively charged backbone of Nafion helps eliminate the crossover problem by coulostatic repulsion with negatively charged BL and LS.

Photo-Uncaging by C(sp3)-C(sp3) Bond Cleavage Restores β-Lapachone Activity.

β-Lapachone is an ortho-naphthoquinone natural product with significant antiproliferative activity but suffers from adverse systemic toxicity. The use of photoremovable protecting groups to covalently inactivate a substrate and then enable controllable release with light in a spatiotemporal manner is an attractive prodrug strategy to limit toxicity. However, visible light-activatable photocages are nearly exclusively enabled by linkages to nucleophilic functional sites such as alcohols, amines, thiols, phosphates, and sulfonates. Herein, we report covalent inactivation of the electrophilic quinone moiety of β-lapachone via a C(sp3)-C(sp3) bond to a coumarin photocage. In contrast to β-lapachone, the designed prodrug remained intact in human whole blood and did not induce methemoglobinemia in the dark. Under light activation, the C-C bond cleaves to release the active quinone, recovering its biological activity when evaluated against the enzyme NQO1 and human cancer cells. Investigations into this report of a C(sp3)-C(sp3) photoinduced bond cleavage suggest a nontraditional, radical-based mechanism of release beginning with an initial charge-transfer excited state. Additionally, caging and release of the isomeric para-quinone, α-lapachone, are demonstrated. As such, we describe a photocaging strategy for the pair of quinones and report a unique light-induced cleavage of a C-C bond. We envision that this photocage strategy can be extended to quinones beyond β- and α-lapachone, thus expanding the chemical toolbox of photocaged compounds.