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Article ; Online: Interactions Between Endocannabinoid and Endogenous Opioid Systems Prospectively Influence Postoperative Opioid Use in Pregnant Patients Undergoing Cesarean Delivery.

Stone, Amanda L / Pham, Amelie / Osmundson, Sarah S / Pedowitz, Alex / Kingsley, Philip J / Marnett, Larry J / Patel, Sachin / Wickersham, Nancy / Sorabella, Laura L / Bruehl, Stephen

The journal of pain

2024 , Page(s) 104548

Abstract: Both endocannabinoid (EC) and endogenous opioid systems are involved in nociceptive processing and may work together synergistically based on preclinical models. This study evaluated the interactive effects of preoperative beta-endorphin concentrations ( ... ...

Abstract	Both endocannabinoid (EC) and endogenous opioid systems are involved in nociceptive processing and may work together synergistically based on preclinical models. This study evaluated the interactive effects of preoperative beta-endorphin concentrations (a key analgesic endogenous opioid) in cerebrospinal fluid (CSF) and ECs (CSF and plasma 2-arachidonoylglycerol [2-AG] and plasma anandamide [AEA]) on postoperative opioid use and pain intensity in a prospective cohort of n = 112 pregnant patients undergoing scheduled cesarean delivery. Maternal blood and CSF samples were collected preoperatively for beta-endorphin and EC assays. Patients completed measures of outpatient opioid use (number of tablets used and days of use) and average pain intensity at 2 weeks postoperatively. Results of general linear model analyses controlling for maternal age, BMI at time of delivery, and race revealed significant multiplicative interactions between EC and beta-endorphin concentrations on number of opioid tablets used (based on pill count), days of opioid use, and total milligram morphine equivalents used in the 2 week follow-up period. Elevated preoperative plasma and CSF 2-AG predicted reduced outpatient opioid analgesic use particularly for patients low in CSF beta-endorphin. Similar analyses for pain intensity at 2-week follow-up indicated a significant interaction (p<.02) characterized by higher preoperative beta-endorphin concentrations being associated with lower subsequent pain only for individuals with low preoperative plasma AEA concentrations. Further exploration of interactions between EC and endogenous opioid inhibitory systems as they influence responses to opioid analgesics in other clinical pain populations may help guide development of precision pain management approaches. PERSPECTIVE: In the postoperative setting of patients undergoing cesarean delivery, elevated endocannabinoids were linked to reduced outpatient opioid analgesic use in individuals who had low endogenous opioid concentrations in cerebrospinal fluid. Further exploration of interactions between these two inhibitory systems as they impact on responses to pain management interventions appears warranted.
Language	English
Publishing date	2024-04-23
Publishing country	United States
Document type	Journal Article
ZDB-ID	2018789-0
ISSN	1528-8447 ; 1526-5900
ISSN (online)	1528-8447
ISSN	1526-5900
DOI	10.1016/j.jpain.2024.104548
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Zs.A 5237: Show issues

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Article ; Online: The Endocannabinoid 2-Arachidonoylglycerol Bidirectionally Modulates Acute and Protracted Effects of Predator Odor Exposure.

Kondev, Veronika / Morgan, Amanda / Najeed, Mustafa / Winters, Nathan D / Kingsley, Philip J / Marnett, Lawrence / Patel, Sachin

Biological psychiatry

2022 Volume 92, Issue 9, Page(s) 739–749

Abstract: Background: Stress-related disorders are among the most prevalent psychiatric disorders, characterized by excess fear and enhanced avoidance of trauma triggers. Elucidating the mechanisms regulating temporally distinct aspects of innate and conditioned ... ...

Abstract	Background: Stress-related disorders are among the most prevalent psychiatric disorders, characterized by excess fear and enhanced avoidance of trauma triggers. Elucidating the mechanisms regulating temporally distinct aspects of innate and conditioned fear responses could facilitate novel therapeutic development for stress-related disorders. One potential target that has recently emerged is the endocannabinoid system, which has been reported to mediate the physiological response to stress and represents an important substrate underlying individual differences in stress susceptibility. Methods: Here, we exposed male and female CD-1 mice to an innate predator stressor, 2MT (2-methyl-2-thiazoline), to investigate the ability of endocannabinoid signaling to modulate temporally distinct innate and conditioned fear behaviors. Results: We found that 2MT exposure increased amygdala 2-AG (2-arachidonoylglycerol) content and selectively increased excitability in central, but not basolateral, amygdala neurons. We also found that pharmacological 2-AG augmentation during stress exposure exacerbated both acute freezing responses and central amygdala hyperexcitability via cannabinoid receptor type 1- and type 2-dependent mechanisms. Finally, 2-AG augmentation during stress exposure reduced long-term contextual conditioned freezing, and 2-AG augmentation 24 hours after stress exposure reduced conditioned avoidance behavior. Conclusions: Our findings demonstrate a bidirectional effect of 2-AG augmentation on innate and conditioned fear behavior, with enhancement of 2-AG levels during stress promoting innate fear responses but ultimately resulting in long-term conditioned fear reduction. These data could reconcile contradictory data on the role of 2-AG in the regulation of innate and conditioned fear-related behavioral responses.
MeSH term(s)	Animals ; Arachidonic Acids ; Endocannabinoids/pharmacology ; Female ; Glycerides ; Male ; Mice ; Odorants ; Piperidines/pharmacology ; Receptors, Cannabinoid
Chemical Substances	Arachidonic Acids ; Endocannabinoids ; Glycerides ; Piperidines ; Receptors, Cannabinoid ; glyceryl 2-arachidonate (8D239QDW64)
Language	English
Publishing date	2022-05-17
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	209434-4
ISSN	1873-2402 ; 0006-3223
ISSN (online)	1873-2402
ISSN	0006-3223
DOI	10.1016/j.biopsych.2022.05.012
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Zs.A 720: Show issues

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Article ; Online: Detection of tyrosine kinase inhibitors-induced COX-2 expression in bladder cancer by fluorocoxib A.

Bourn, Jennifer / Pandey, Sony / Uddin, Jashim / Marnett, Lawrence / Cekanova, Maria

Oncotarget

2019 Volume 10, Issue 50, Page(s) 5168–5180

Abstract: Among challenges of targeted therapies is the activation of alternative pro-survival signaling pathways in cancer cells, resulting in an acquired drug resistance. Cyclooxygenase-2 (COX-2) is overexpressed in bladder cancer cells, making it an attractive ... ...

Abstract	Among challenges of targeted therapies is the activation of alternative pro-survival signaling pathways in cancer cells, resulting in an acquired drug resistance. Cyclooxygenase-2 (COX-2) is overexpressed in bladder cancer cells, making it an attractive molecular target for the detection and treatment of cancer. Fluorocoxib A is an optical imaging agent that selectively targets COX-2. In this study, we evaluated the ability of fluorocoxib A to monitor the responses of bladder cancer to targeted therapies
Language	English
Publishing date	2019-08-27
Publishing country	United States
Document type	Journal Article
ZDB-ID	2560162-3
ISSN	1949-2553 ; 1949-2553
ISSN (online)	1949-2553
ISSN	1949-2553
DOI	10.18632/oncotarget.27125
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Article ; Online: Jedi-1/MEGF12-mediated phagocytosis controls the pro-neurogenic properties of microglia in the ventricular-subventricular zone.

Morrison, Vivianne / Houpert, Matthew / Trapani, Jonathan / Brockman, Asa / Kingsley, Philip / Katdare, Ketaki / Layden, Hillary / Nguena-Jones, Gabriela / Trevisan, Alexandra / Maguire-Zeiss, Kathleen / Marnett, Lawrence / Bix, Gregory / Ihrie, Rebecca / Carter, Bruce

Cell reports

2023 Volume 42, Issue 11, Page(s) 113423

Abstract: Microglia are the primary phagocytes in the central nervous system and clear dead cells generated during development or disease. The phagocytic process shapes the microglia phenotype, which affects the local environment. A unique population of microglia ... ...

Abstract	Microglia are the primary phagocytes in the central nervous system and clear dead cells generated during development or disease. The phagocytic process shapes the microglia phenotype, which affects the local environment. A unique population of microglia resides in the ventricular-subventricular zone (V-SVZ) of neonatal mice, but how they influence the neurogenic niche is not well understood. Here, we demonstrate that phagocytosis contributes to a pro-neurogenic microglial phenotype in the V-SVZ and that these microglia phagocytose apoptotic cells via the engulfment receptor Jedi-1. Deletion of Jedi-1 decreases apoptotic cell clearance, triggering a neuroinflammatory microglia phenotype that resembles dysfunctional microglia in neurodegeneration and aging and that reduces neural precursor proliferation via elevated interleukin-1β signaling; interleukin-1 receptor inhibition rescues precursor proliferation in vivo. Together, these results reveal a critical role for Jedi-1 in connecting microglial phagocytic activity to the maintenance of a pro-neurogenic phenotype in the developing V-SVZ.
MeSH term(s)	Animals ; Mice ; Lateral Ventricles ; Microglia/physiology ; Phagocytes ; Phagocytosis/physiology ; Signal Transduction
Chemical Substances	PEAR1 protein, mouse
Language	English
Publishing date	2023-11-11
Publishing country	United States
Document type	Journal Article
ZDB-ID	2649101-1
ISSN	2211-1247 ; 2211-1247
ISSN (online)	2211-1247
ISSN	2211-1247
DOI	10.1016/j.celrep.2023.113423
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Article ; Online: Electrophilic Modification of PKM2 by 4-Hydroxynonenal and 4-Oxononenal Results in Protein Cross-Linking and Kinase Inhibition.

Camarillo, Jeannie M / Ullery, Jody C / Rose, Kristie L / Marnett, Lawrence J

Chemical research in toxicology

2017 Volume 30, Issue 2, Page(s) 635–641

Abstract: Rapidly proliferating cells require an increased rate of metabolism to allow for the production of nucleic acids, amino acids, and lipids. Pyruvate kinase catalyzes the final step in the glycolysis pathway, and different isoforms display vastly different ...

Abstract	Rapidly proliferating cells require an increased rate of metabolism to allow for the production of nucleic acids, amino acids, and lipids. Pyruvate kinase catalyzes the final step in the glycolysis pathway, and different isoforms display vastly different catalytic efficiencies. The M2 isoform of pyruvate kinase (PKM2) is strongly expressed in cancer cells and contributes to aerobic glycolysis in what is commonly termed the Warburg effect. Here, we show that PKM2 is covalently modified by the lipid electrophiles 4-hydroxy-2-nonenal (HNE) and 4-oxo-2-nonenal (ONE). HNE and ONE modify multiple sites on PKM2 in vitro, including Cys424 and His439, which play a role in protein-protein interactions and fructose 1,6-bis-phosphate binding, respectively. Modification of these sites results in a dose-dependent decrease in enzymatic activity. In addition, high concentrations of the electrophile, most notably in the case of ONE, result in substantial protein-protein cross-linking in vitro and in cells. Exposure of RKO cells to electrophiles results in modification of monomeric PKM2 in a dose-dependent manner. There is a concomitant decrease in PKM2 activity in cells upon ONE exposure, but not HNE exposure. Together, our data suggest that modification of PKM2 by certain electrophiles results in kinase inactivation.
MeSH term(s)	Aldehydes/pharmacology ; Cell Line, Tumor ; Chromatography, Liquid ; Click Chemistry ; Enzyme Inhibitors/pharmacology ; Humans ; Ketones/pharmacology ; Pyruvate Kinase/antagonists & inhibitors ; Pyruvate Kinase/metabolism ; Tandem Mass Spectrometry
Chemical Substances	Aldehydes ; Enzyme Inhibitors ; Ketones ; 4-oxopentanal (BL58BK264G) ; Pyruvate Kinase (EC 2.7.1.40) ; 4-hydroxy-2-nonenal (K1CVM13F96)
Language	English
Publishing date	2017-01-03
Publishing country	United States
Document type	Journal Article
ZDB-ID	639353-6
ISSN	1520-5010 ; 0893-228X
ISSN (online)	1520-5010
ISSN	0893-228X
DOI	10.1021/acs.chemrestox.6b00374
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Zs.A 2320: Show issues

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Article ; Online: Discovery of a Redox-Activatable Chemical Probe for Detection of Cyclooxygenase-2 in Cells and Animals.

Uddin, Md Jashim / Lo, Justin Han-Je / Oltman, Connor G / Crews, Brenda C / Huda, Tamanna / Liu, Justin / Kingsley, Philip J / Lin, Shuyang / Milad, Mathew / Aleem, Ansari M / Asaduzzaman, Abu / McIntyre, J Oliver / Duvall, Craig L / Marnett, Lawrence J

ACS chemical biology

2022 Volume 17, Issue 7, Page(s) 1714–1722

Abstract: Cyclooxygenase-2 (COX-2) expression is up-regulated in inflammatory tissues and many premalignant and malignant tumors. Assessment of COX-2 protein in vivo, therefore, promises to be a powerful strategy to distinguish pathologic cells from normal cells ... ...

Abstract	Cyclooxygenase-2 (COX-2) expression is up-regulated in inflammatory tissues and many premalignant and malignant tumors. Assessment of COX-2 protein in vivo, therefore, promises to be a powerful strategy to distinguish pathologic cells from normal cells in a complex disease setting. Herein, we report the first redox-activatable COX-2 probe, fluorocoxib Q (FQ), for in vivo molecular imaging of pathogenesis. FQ inhibits COX-2 selectively in purified enzyme and cell-based assays. FQ exhibits extremely low fluorescence and displays time- and concentration-dependent fluorescence enhancement upon exposure to a redox environment. FQ enters the cells freely and binds to the COX-2 enzyme. FQ exhibits high circulation half-life and metabolic stability sufficient for target site accumulation and demonstrates COX-2-targeted uptake and retention in cancer cells and pathologic tissues. Once taken up, it undergoes redox-mediated transformation into a fluorescent compound fluorocoxib Q-H that results in high signal-to-noise contrast and differentiates pathologic tissues from non-pathologic tissues for real-time in vivo imaging.
MeSH term(s)	Animals ; Cyclooxygenase 2/metabolism ; Cyclooxygenase 2 Inhibitors/pharmacology ; Fluorescent Dyes/chemistry ; Neoplasms ; Oxidation-Reduction
Chemical Substances	Cyclooxygenase 2 Inhibitors ; Fluorescent Dyes ; Cyclooxygenase 2 (EC 1.14.99.1)
Language	English
Publishing date	2022-07-05
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, N.I.H., Extramural
ISSN	1554-8937
ISSN (online)	1554-8937
DOI	10.1021/acschembio.1c00961
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Article ; Online: Site-Specific Synthesis of Oligonucleotides Containing 6-Oxo-M

Christov, Plamen P / Richie-Jannetta, Robyn / Kingsley, Philip J / Vemulapalli, Anoop / Kim, Kwangho / Sulikowski, Gary A / Rizzo, Carmelo J / Ketkar, Amit / Eoff, Robert L / Rouzer, Carol A / Marnett, Lawrence J

Chemical research in toxicology

2021 Volume 34, Issue 12, Page(s) 2567–2578

Abstract: The lipid peroxidation product malondialdehyde and the DNA peroxidation product base-propenal react with dG to generate the exocyclic adduct, ... ...

Abstract	The lipid peroxidation product malondialdehyde and the DNA peroxidation product base-propenal react with dG to generate the exocyclic adduct, M
MeSH term(s)	Chromatography, Liquid ; DNA-Directed DNA Polymerase/metabolism ; Deoxyguanosine/analogs & derivatives ; Deoxyguanosine/chemistry ; Deoxyguanosine/metabolism ; Humans ; Molecular Structure ; Oligonucleotides/chemical synthesis ; Oligonucleotides/chemistry ; Oligonucleotides/metabolism ; Tandem Mass Spectrometry ; DNA Polymerase iota
Chemical Substances	Oligonucleotides ; DNA-Directed DNA Polymerase (EC 2.7.7.7) ; Deoxyguanosine (G9481N71RO) ; DNA Polymerase iota (EC 2.7.7.7) ; POLI protein, human (EC 2.7.7.7)
Language	English
Publishing date	2021-12-03
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	639353-6
ISSN	1520-5010 ; 0893-228X
ISSN (online)	1520-5010
ISSN	0893-228X
DOI	10.1021/acs.chemrestox.1c00334
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Article ; Online: Mass spectrometric methods for the analysis of nucleoside-protein cross-links: application to oxopropenyl-deoxyadenosine.

Shuck, Sarah C / Rose, Kristie L / Marnett, Lawrence J

Chemical research in toxicology

2013 Volume 27, Issue 1, Page(s) 136–146

Abstract: Electrophilic DNA adducts produced following oxidative stress can form DNA-protein cross-links (DPCs), dramatically altering genomic maintenance pathways. Complete characterization of DPCs has been hindered, in part, because of a lack of comprehensive ... ...

Abstract	Electrophilic DNA adducts produced following oxidative stress can form DNA-protein cross-links (DPCs), dramatically altering genomic maintenance pathways. Complete characterization of DPCs has been hindered, in part, because of a lack of comprehensive techniques for their analysis. We have, therefore, established a proteomics approach to investigate sites of cross-link formation using N(6)-(3-oxo-1-propenyl)-2'-deoxyadenosine (OPdA), an electrophilic DNA adduct produced from oxidative stress. OPdA was reacted with albumin and reduced with NaBH4 to stabilize DPCs. Using LC-MS/MS proteomics techniques, high-resolution peptide sequence data were obtained; however, using a database searching strategy, adducted peptides were only identified in samples subjected to chemical depurination. This strategy revealed multiple oxopropenyl adenine-lysine adducts and oxopropenyl-lysine adducts with the most reactive lysines identified to be Lys256 and Lys548. Manual interrogation of the mass spectral data provided evidence of OPdA deoxynucleoside conjugates to lysines and cross-links that underwent facile collision-induced dissociation to release an unmodified peptide without subsequent fragmentation. These fragmentations precluded adduct detection and peptide sequencing using database searching methods. Thus, comprehensive analysis of DPCs requires chemical depurination of DNA-protein reaction mixtures followed by a combination of database-dependent and manual interrogation of LC-MS/MS data using higher-energy collision-induced dissociation. In the present case, this approach revealed that OPdA selectively modifies surface lysine residues and produces nucleoside-protein cross-links and oxopropenyl lysine.
MeSH term(s)	Animals ; Cattle ; Chromatography, Liquid ; Cross-Linking Reagents/chemistry ; DNA Adducts/analysis ; DNA Adducts/chemistry ; Deoxyadenosines/chemistry ; Lysine/analogs & derivatives ; Lysine/chemistry ; Models, Molecular ; Molecular Structure ; Nucleosides/analysis ; Nucleosides/chemistry ; Oxidative Stress ; Proteomics ; Serum Albumin, Bovine/analysis ; Serum Albumin, Bovine/chemistry ; Tandem Mass Spectrometry
Chemical Substances	Cross-Linking Reagents ; DNA Adducts ; Deoxyadenosines ; N6-oxopropenyl-2'-deoxyadenosine ; Nucleosides ; N(alpha)-acetyllysine (1946-82-3) ; Serum Albumin, Bovine (27432CM55Q) ; Lysine (K3Z4F929H6)
Language	English
Publishing date	2013-12-20
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	639353-6
ISSN	1520-5010 ; 0893-228X
ISSN (online)	1520-5010
ISSN	0893-228X
DOI	10.1021/tx400384e
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Article: Cyclooxygenase mechanisms.

Marnett, L J

Current opinion in chemical biology

2000 Volume 4, Issue 5, Page(s) 545–552

Abstract: Several advances have occurred in the past year in our understanding of cyclooxygenase catalysis. The role of specific heme oxidation states in the formation of catalytically competent tyrosyl radicals has been defined; the identity of physiological ... ...

Abstract	Several advances have occurred in the past year in our understanding of cyclooxygenase catalysis. The role of specific heme oxidation states in the formation of catalytically competent tyrosyl radicals has been defined; the identity of physiological hydroperoxide activators has been established; and the participation of individual amino acids in substrate binding and oxygenation has been elucidated.
MeSH term(s)	Arachidonic Acid/metabolism ; Binding Sites ; Heme/metabolism ; Oxidants/metabolism ; Prostaglandin-Endoperoxide Synthases/metabolism ; Substrate Specificity
Chemical Substances	Oxidants ; Arachidonic Acid (27YG812J1I) ; Heme (42VZT0U6YR) ; Prostaglandin-Endoperoxide Synthases (EC 1.14.99.1)
Language	English
Publishing date	2000-10
Publishing country	England
Document type	Journal Article ; Research Support, U.S. Gov't, P.H.S. ; Review
ZDB-ID	1439176-4
ISSN	1879-0402 ; 1367-5931
ISSN (online)	1879-0402
ISSN	1367-5931
DOI	10.1016/s1367-5931(00)00130-7
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Zs.A 4986: Show issues

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Article: Structure, function and inhibition of cyclo-oxygenases.

Marnett, L J

Ernst Schering Research Foundation workshop

2000 , Issue 31, Page(s) 65–83

MeSH term(s)	Animals ; Catalysis ; Cyclooxygenase 2 ; Cyclooxygenase 2 Inhibitors ; Cyclooxygenase Inhibitors/classification ; Cyclooxygenase Inhibitors/pharmacology ; Humans ; Isoenzymes/chemistry ; Isoenzymes/metabolism ; Isoenzymes/pharmacology ; Membrane Proteins ; Oxidants/metabolism ; Prostaglandin-Endoperoxide Synthases/chemistry ; Prostaglandin-Endoperoxide Synthases/metabolism ; Prostaglandin-Endoperoxide Synthases/pharmacology ; Stereoisomerism ; Substrate Specificity
Chemical Substances	Cyclooxygenase 2 Inhibitors ; Cyclooxygenase Inhibitors ; Isoenzymes ; Membrane Proteins ; Oxidants ; Cyclooxygenase 2 (EC 1.14.99.1) ; PTGS2 protein, human (EC 1.14.99.1) ; Prostaglandin-Endoperoxide Synthases (EC 1.14.99.1)
Language	English
Publishing date	2000
Publishing country	Germany
Document type	Journal Article ; Research Support, U.S. Gov't, P.H.S. ; Review
ISSN	0947-6075
ISSN	0947-6075
DOI	10.1007/978-3-662-04047-8_4
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