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  1. Article ; Online: Carboxyethylpyrroles: From Hypothesis to the Discovery of Biologically Active Natural Products.

    Salomon, Robert G

    Chemical research in toxicology

    2017  Volume 30, Issue 1, Page(s) 105–113

    Abstract: Our research on the roles of lipid oxidation in human disease is guided by chemical intuition. For example, we postulated that 2-(ω-carboxyethyl)pyrrole (CEP) derivatives of primary amines would be produced through covalent adduction of a γ- ... ...

    Abstract Our research on the roles of lipid oxidation in human disease is guided by chemical intuition. For example, we postulated that 2-(ω-carboxyethyl)pyrrole (CEP) derivatives of primary amines would be produced through covalent adduction of a γ-hydroxyalkenal generated, in turn, through oxidative fragmentation of docosahexaenoates. Our studies confirmed the natural occurrence of this chemistry, and the biological activities of these natural products and their extensive involvements in human physiology (wound healing) and pathology (age-related macular degeneration, autism, atherosclerosis, sickle cell disease, and tumor growth) continue to emerge. This perspective recounts these discoveries and proposes new frontiers where further developments are likely. Perhaps more significantly, it depicts an effective chemistry-based approach to the discovery of novel biochemistry.
    MeSH term(s) Animals ; Biological Products/metabolism ; Humans ; Pyrroles/metabolism
    Chemical Substances Biological Products ; Pyrroles
    Language English
    Publishing date 2017--17
    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.6b00304
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  2. Article ; Online: Structural identification and cardiovascular activities of oxidized phospholipids.

    Salomon, Robert G

    Circulation research

    2012  Volume 111, Issue 7, Page(s) 930–946

    Abstract: Free radical-induced oxidation of membrane phospholipids generates complex mixtures of oxidized phospholipids (oxPLs). The combinatorial operation of a few dozen reaction types on a few dozen phospholipid structures results in the production of a ... ...

    Abstract Free radical-induced oxidation of membrane phospholipids generates complex mixtures of oxidized phospholipids (oxPLs). The combinatorial operation of a few dozen reaction types on a few dozen phospholipid structures results in the production of a dauntingly vast diversity of oxPL molecular species. Structural identification of the individual oxPL in these mixtures is a redoubtable challenge that is absolutely essential to allow determination of the biological activities of individual species. With an emphasis on cardiovascular consequences, this Review focuses on biological activities of oxPLs whose molecular structures are known and highlights 2 diametrically opposite approaches that were used to determine those structures, that is, (1) the classic approach from bioactivity of a complex mixture to isolation and structural characterization of the active molecule followed by confirmation of the structure by unambiguous chemical synthesis and (2) hypothesis of products that are likely to be generated by lipid oxidation, followed by synthesis, and then detection in vivo guided by the availability of authentic standards, and last, characterization of biological activities. Especially important for the application of the second paradigm is the capability of LC-MS/MS and derivatizations to selectively detect and quantify specific oxPL in complex mixtures, without the need for their isolation or complete separation. This technology can provide strong evidence for identity by comparisons with pure, well-characterized samples available by chemical syntheses. Those pure samples are critical for determining the biological activities attributable to specific molecular species of oxPLs in the complex mixtures generated in vivo as a consequence of oxidative stress.
    MeSH term(s) Animals ; Atherosclerosis/physiopathology ; Cardiovascular Diseases/physiopathology ; Cardiovascular Physiological Phenomena ; Humans ; Inflammation/physiopathology ; Neovascularization, Physiologic/physiology ; Oxidation-Reduction ; Phospholipids/chemistry ; Phospholipids/physiology ; Thrombosis/physiopathology
    Chemical Substances Phospholipids
    Language English
    Publishing date 2012-09-13
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Review
    ZDB-ID 80100-8
    ISSN 1524-4571 ; 0009-7330 ; 0931-6876
    ISSN (online) 1524-4571
    ISSN 0009-7330 ; 0931-6876
    DOI 10.1161/CIRCRESAHA.112.275388
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  3. Article: The Impact of Prior Breast Augmentation on Breast Reconstruction after Mastectomy.

    Clegg, Devin J / Salomon, Brett J / Porter, Christopher G / Mazonas, Thomas W / Heidel, Robert E / Stephenson, Stacy M / Herbig, Kathleen S / Chun, Joseph T / Lloyd, Jillian M / Boukovalas, Stefanos

    Plastic and reconstructive surgery. Global open

    2023  Volume 11, Issue 5, Page(s) e5025

    Abstract: The risk of women developing breast cancer after augmentation mammaplasty may be lower than the general population, with minimal current literature on breast reconstruction in this population. We sought to evaluate the impact of previous augmentation on ... ...

    Abstract The risk of women developing breast cancer after augmentation mammaplasty may be lower than the general population, with minimal current literature on breast reconstruction in this population. We sought to evaluate the impact of previous augmentation on postmastectomy breast reconstruction.
    Methods: Retrospective review of patients who underwent mastectomies from 2017 to 2021 at our institution was performed. Analysis included frequencies and percentages, descriptive statistics, chi-square analysis, and Fisher exact test.
    Results: Four hundred seventy patients were included, with average body mass index of 29.1 kg/m
    Conclusions: Previously augmented patients were more likely to undergo reconstruction after mastectomy at our institution. All reconstructed augmented patients underwent alloplastic reconstruction, with most performed immediately in staged fashion. Most patients favored silicone implants and maintained the same implant type and plane of reconstruction, with increased implant volume. Larger studies are required to further investigate these trends.
    Language English
    Publishing date 2023-05-22
    Publishing country United States
    Document type Journal Article
    ZDB-ID 2851682-5
    ISSN 2169-7574 ; 2169-7574
    ISSN (online) 2169-7574
    ISSN 2169-7574
    DOI 10.1097/GOX.0000000000005025
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  4. Article: The Impact of Travel Distance and Income on Breast Reconstruction after Mastectomy in a Rural Population.

    Clegg, Devin J / Salomon, Brett J / Porter, Christopher G / Mazonas, Thomas W / Heidel, Robert E / Chun, Joseph T / Herbig, Kathleen S / Stephenson, Stacy M / Lloyd, Jillian M / Boukovalas, Stefanos

    Plastic and reconstructive surgery. Global open

    2023  Volume 11, Issue 2, Page(s) e4802

    Abstract: Factors that influence breast reconstruction after mastectomy have been previously examined in national databases. The purpose of this study was to determine the impact of patient travel distance and income on breast reconstruction after mastectomy in a ... ...

    Abstract Factors that influence breast reconstruction after mastectomy have been previously examined in national databases. The purpose of this study was to determine the impact of patient travel distance and income on breast reconstruction after mastectomy in a rural population.
    Methods: Retrospective review of mastectomy patients from 2017 to 2021 was performed from our prospectively enrolled tumor registry. Analysis included frequencies and percentages, descriptive statistics,
    Results: In total, 462 patients were included. Median BMI was 27.6 kg/m
    Conclusions: Travel distance did not significantly impact reconstruction rates after mastectomy, while household income did on univariable analysis. Studies at an institutional or regional level remain valuable, especially in populations that may not be accurately represented in larger database studies. Our findings highlight the importance of patient education, resource allocation, and multidisciplinary approach to breast cancer care, especially in the rural setting.
    Language English
    Publishing date 2023-02-02
    Publishing country United States
    Document type Journal Article
    ZDB-ID 2851682-5
    ISSN 2169-7574 ; 2169-7574
    ISSN (online) 2169-7574
    ISSN 2169-7574
    DOI 10.1097/GOX.0000000000004802
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  5. Article ; Online: Isolevuglandin adducts in disease.

    Salomon, Robert G / Bi, Wenzhao

    Antioxidants & redox signaling

    2015  Volume 22, Issue 18, Page(s) 1703–1718

    Abstract: Significance: A diverse family of lipid-derived levulinaldehydes, isolevuglandins (isoLGs), is produced by rearrangement of endoperoxide intermediates generated through both cyclooxygenase (COX) and free radical-induced cyclooxygenation of ... ...

    Abstract Significance: A diverse family of lipid-derived levulinaldehydes, isolevuglandins (isoLGs), is produced by rearrangement of endoperoxide intermediates generated through both cyclooxygenase (COX) and free radical-induced cyclooxygenation of polyunsaturated fatty acids and their phospholipid esters. The formation and reactions of isoLGs with other biomolecules has been linked to alcoholic liver disease, Alzheimer's disease, age-related macular degeneration, atherosclerosis, cardiac arythmias, cancer, end-stage renal disease, glaucoma, inflammation of allergies and infection, mitochondrial dysfunction, multiple sclerosis, and thrombosis. This review chronicles progress in understanding the chemistry of isoLGs, detecting their production in vivo and understanding their biological consequences.
    Critical issues: IsoLGs have never been isolated from biological sources, because they form adducts with primary amino groups of other biomolecules within seconds. Chemical synthesis enabled investigation of isoLG chemistry and detection of isoLG adducts present in vivo.
    Recent advances: The first peptide mapping and sequencing of an isoLG-modified protein present in human retina identified the modification of a specific lysyl residue of the sterol C27-hydroxylase Cyp27A1. This residue is preferentially modified by iso[4]LGE2 in vitro, causing loss of function. Adduction of less than one equivalent of isoLG can induce COX-associated oligomerization of the amyloid peptide Aβ1-42. Adduction of isoLGE2 to phosphatidylethanolamines causes gain of function, converting them into proinflammatory isoLGE2-PE agonists that foster monocyte adhesion to endothelial cells.
    Future directions: Among the remaining questions on the biochemistry of isoLGs are the dependence of biological activity on isoLG isomer structure, the structures and mechanism of isoLG-derived protein-protein and DNA-protein cross-link formation, and its biological consequences.
    MeSH term(s) Amyloid/chemistry ; Amyloid/metabolism ; Animals ; Blood-Brain Barrier/pathology ; DNA-Binding Proteins/metabolism ; Fatty Acids, Unsaturated/metabolism ; Humans ; Inflammation/metabolism ; Mitochondria/metabolism ; Oxidative Stress ; Phosphatidylethanolamines/chemistry ; Phosphatidylethanolamines/metabolism ; Prostaglandin-Endoperoxide Synthases/metabolism ; Prostaglandins E/chemistry ; Prostaglandins E/metabolism ; Protein Binding ; Pyrrolidines/chemistry ; Pyrrolidines/metabolism ; Tubulin/chemistry ; Tubulin/metabolism
    Chemical Substances Amyloid ; DNA-Binding Proteins ; Fatty Acids, Unsaturated ; Phosphatidylethanolamines ; Prostaglandins E ; Pyrrolidines ; Tubulin ; Prostaglandin-Endoperoxide Synthases (EC 1.14.99.1)
    Language English
    Publishing date 2015-06-20
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Review
    ZDB-ID 1483836-9
    ISSN 1557-7716 ; 1523-0864
    ISSN (online) 1557-7716
    ISSN 1523-0864
    DOI 10.1089/ars.2014.6154
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    Zs.A 5488: Show issues Location:
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  6. Article ; Online: 4-Hydroxy-7-oxo-5-heptenoic acid lactone can induce mitochondrial dysfunction in retinal pigmented epithelial cells.

    Cheng, Yu-Shiuan / Linetsky, Mikhail / Li, Haoting / Ayyash, Naji / Gardella, Anthony / Salomon, Robert G

    Free radical biology & medicine

    2020  Volume 160, Page(s) 719–733

    Abstract: Oxidation of docosahexaenoate (DHA)-containing phospholipids in the cell plasma membrane leads to release of the α,β-unsaturated aldehyde 4-hydroxy-7-oxo-5-heptenoic acid (HOHA) lactone which is capable of inducing retinal pigmented epithelial (RPE) cell ...

    Abstract Oxidation of docosahexaenoate (DHA)-containing phospholipids in the cell plasma membrane leads to release of the α,β-unsaturated aldehyde 4-hydroxy-7-oxo-5-heptenoic acid (HOHA) lactone which is capable of inducing retinal pigmented epithelial (RPE) cell dysfunction. Previously, HOHA lactone was shown to induce apoptosis and angiogenesis, and to activate the alternative complement pathway. RPE cells metabolize HOHA lactone through enzymatic conjugation with glutathione (GSH). Competing with this process is the adduction of HOHA lactone to protein lysyl residues generating 2-(ω-carboxyethyl)pyrrole (CEP) derivatives that have pathological relevance to age-related macular degeneration (AMD). We now find that HOHA lactone induces mitochondrial dysfunction. It decreases ATP levels, mitochondrial membrane potentials, enzymatic activities of mitochondrial complexes, depletes GSH and induces oxidative stress in RPE cells. The present study confirmed that pyridoxamine and other primary amines, which have been shown to scavenge γ-ketoaldehydes formed by carbohydrate or lipid peroxidation, are ineffective for scavenging the α,β-unsaturated aldehydes. Histidyl hydrazide (HH), that has both hydrazide and imidazole nucleophile functionalities, is an effective scavenger of HOHA lactone and it protects ARPE-19 cells against HOHA lactone-induced cytotoxicity. The HH α-amino group is not essential for this electrophile trapping activity. The N
    MeSH term(s) Epithelial Cells ; Lactones/metabolism ; Lactones/toxicity ; Mitochondria ; Oxidative Stress ; Retinal Pigment Epithelium/metabolism
    Chemical Substances 4-hydroxy-7-oxo-5-heptenoic acid lactone ; Lactones
    Language English
    Publishing date 2020-09-10
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ZDB-ID 807032-5
    ISSN 1873-4596 ; 0891-5849
    ISSN (online) 1873-4596
    ISSN 0891-5849
    DOI 10.1016/j.freeradbiomed.2020.09.009
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  7. Article ; Online: Cysteinyl leukotriene-like metabolites are generated in retinal pigment epithelial cells through glutathionylation/reduction of an oxidatively truncated fragment of arachidonate

    Mikhail Linetsky / Anshula Mondal / Si-Yang Liu / Abby M. Hite / Shravani Enduri / Yu-Shiuan Cheng / Beatriz Feijo / Graham Kang / Nana Arhin / Hong Zeng / Olivia R. Laniak / John Denker / Robert G. Salomon

    Results in Chemistry, Vol 6, Iss , Pp 100995- (2023)

    2023  

    Abstract: ... enzymes, e.g., 5-lipoxygenase, are not involved in the generation of øLTs in vivo, inhibitors of LT ... biosynthesis, e.g., Zileuton, are not expected to prevent the generation of øLTs. On the other hand, if øLTs ... antagonist drugs, e.g., Montelukast, may include inhibition not only of LT-induced but also øLT-induced LT receptor ...

    Abstract γ-Hydroxyalkenals, 4-hydroxynonenal (HNE) and phospholipid esters of 4-hydroxy-8-oxooctenoic acid (HOOA-PL), are produced from the alkyl and carboxyl termini of arachidonyl phospholipids by radical-induced oxidative cleavage. Metabolism of HNE by Michael addition of glutathione (GSH) followed by reduction of the aldehyde carbonyl produces a GSH derivative of 1,4-dihydroxynonane (DHN)-GSH. Analogous biochemistry was anticipated to produce a GSH derivative of 5,8-dihydroxyoctanoic acid (DHOA-GSH) that has structural and functional similarity to the cysteinyl leukotriene (LT)C4. We now report that exposure of human retinal pigment epithelial cells to CoCl2, an in vitro model of hypoxia-induced oxidative stress, generates DHOA-GSH and two products of its peptidolysis, DHOA-CysGly and DHOA-Cys that resemble LTD4 and LTE4. Identification of these metabolites was confirmed by unambiguous chemical syntheses that also provided a heavy isotope labeled quantitative standard 13C215N-DHOA-GSH. The availability of pure samples of these arachidonate metabolites will enable assessment of their biological activities, and testing the hypothesis that øLTs promote pathological inflammation by serving as LT receptor agonists. Because LT biosynthetic enzymes, e.g., 5-lipoxygenase, are not involved in the generation of øLTs in vivo, inhibitors of LT biosynthesis, e.g., Zileuton, are not expected to prevent the generation of øLTs. On the other hand, if øLTs are leukotriene receptor agonists, then the therapeutic effects of leukotriene receptor antagonist drugs, e.g., Montelukast, may include inhibition not only of LT-induced but also øLT-induced LT receptor activation and signaling.
    Keywords Pseudo leukotrienes ; Retinal Pigment Epithelial Cells ; Free radical-induced lipid oxidation ; Hypoxia-inducible factor ; Chemistry ; QD1-999
    Subject code 500
    Language English
    Publishing date 2023-12-01T00:00:00Z
    Publisher Elsevier
    Document type Article ; Online
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  8. Article ; Online: Total Synthesis Confirms the Molecular Structure Proposed for Oxidized Levuglandin D

    Cheng, Yu-Shiuan / Yu, Wenyuan / Xu, Yunfeng / Salomon, Robert G

    Journal of natural products

    2017  Volume 80, Issue 2, Page(s) 488–498

    Abstract: Levuglandins (LG) ... ...

    Abstract Levuglandins (LG)D
    MeSH term(s) Animals ; Gracilaria/chemistry ; Humans ; Mice ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Oxidation-Reduction ; Phorbol Esters/pharmacology ; Prostaglandin D2/analogs & derivatives ; Prostaglandin D2/chemical synthesis ; Prostaglandin D2/chemistry ; Proteins/metabolism
    Chemical Substances Phorbol Esters ; Proteins ; levuglandin D2 ; phorbol-12-myristate (20839-06-9) ; Prostaglandin D2 (RXY07S6CZ2)
    Language English
    Publishing date 2017-02-14
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.6b01048
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  9. Article ; Online: 4-Hydroxy-7-oxo-5-heptenoic acid lactone is a potent inducer of brain cancer cell invasiveness that may contribute to the failure of anti-angiogenic therapies.

    Tomko, Nicholas / Kluever, Mark / Wu, Chunying / Zhu, Junqing / Wang, Yanming / Salomon, Robert G

    Free radical biology & medicine

    2019  Volume 146, Page(s) 234–256

    Abstract: ... to the more aggressive mesenchymal phenotype, e.g., after treatment with an anti-angiogenic therapy, is ...

    Abstract Previously, we discovered that free radical-induced oxidative fragmentation of the docosahexaenoate ester of 2-lysophosphatidylcholine produces 4-hydroxy-7-oxo-5-heptenoic acid (HOHA) lactone that, in turn, promotes the migration and invasion of endothelial cells. This suggested that HOHA lactone might similarly promote migration and invasion of glioblastoma multiformae (GBM) brain cancer stem cells (CSCs). A bioinformatics analysis of clinical cancer genomic data revealed that matrix metalloproteinase (MMP)1 and three markers of oxidative stress - superoxide dismutase 2, NADPH oxidase 4, and carbonic anhydrase 9 - are upregulated in human mesenchymal GBM cancer tissue, and that MMP1 is positively correlated to all three of these oxidative stress markers. In addition, elevated levels of MMP1 are indicative of GBM invasion, while low levels of MMP1 indicate survival. We also explored the hypothesis that the transition from the proneural to the more aggressive mesenchymal phenotype, e.g., after treatment with an anti-angiogenic therapy, is promoted by the effects of lipid oxidation products on GBM CSCs. We found that low micromolar concentrations of HOHA lactone increase the cell migration velocity of cultured GBM CSCs, and induce the expression of MMP1 and two protein biomarkers of the proneural to mesenchymal transition (PMT): p65 NF-κβ and vimentin. Exposure of cultured GBM CSCs to HOHA lactone causes an increase in phosphorylation of mitogen-activated protein kinases and Akt kinases that are dependent on both protease-activated receptor 1 (PAR1) and MMP1 activity. We conclude that HOHA lactone promotes the PMT in GBM through the activation of PAR1 and MMP1. This contributes to a fatal flaw in antiangiogenic, chemo, and radiation therapies: they promote oxidative stress and the generation of HOHA lactone in the tumor that fosters a change from the proliferative proneural to the migratory mesenchymal GBM CSC phenotype that seeds new tumor growth. Inhibition of PAR1 and HOHA lactone are potential new therapeutic targets for impeding GBM tumor recurrence.
    MeSH term(s) Brain ; Brain Neoplasms/genetics ; Cell Line, Tumor ; Cell Movement ; Endothelial Cells ; Glioblastoma/drug therapy ; Glioblastoma/genetics ; Humans ; Lactones/pharmacology ; Neoplasm Invasiveness ; Neoplasm Recurrence, Local
    Chemical Substances 4-hydroxy-7-oxo-5-heptenoic acid lactone ; Lactones
    Language English
    Publishing date 2019-11-09
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural
    ZDB-ID 807032-5
    ISSN 1873-4596 ; 0891-5849
    ISSN (online) 1873-4596
    ISSN 0891-5849
    DOI 10.1016/j.freeradbiomed.2019.11.009
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  10. Article: Evaluation of Pollen Production of Common Male Date Palms Grown in the Mexicali Valley, Mexico

    Salomón-Torres, Ricardo / Ortiz-Uribe, Noé / Krueger, Robert / García-Vázquez, Juan Pablo / Cohen, Yuval / Wright, Glenn C. / Samaniego-Sandoval, Laura

    Agriculture (Basel). 2022 Aug. 18, v. 12, no. 8

    2022  

    Abstract: ... The pollen was extracted manually, with average production among all individuals of 780.94 and 777.11 g ... 7 and 32.55 g, while that of the latest one produced 10.70 g and 18.28 g for each year, respectively ... of pollen with 1250.98 and 1114.26 g on average for each year, produced during a late, short flowering ...

    Abstract The aim of this study was the evaluation of date palm (Phoenix dactylifera L.) pollen production during the 2021 and 2022 seasons in the Mexicali Valley, Mexico. Twelve seed-propagated male palms of 20 years of age and similar vigor were selected and grouped into four groups with phenotypic characteristics of the common female cultivars in the area (Medjool, Deglet Noor, Khadrawy, and Zahidi). The pollen was extracted manually, with average production among all individuals of 780.94 and 777.11 g, in 26 and 24 inflorescences, respectively, for each year. Likewise, the flowering period on average was 47 and 41 days for each year. The pollen extracted from the earliest four inflorescences averaged 38.7 and 32.55 g, while that of the latest one produced 10.70 g and 18.28 g for each year, respectively. Seedling male palms with a phenotype similar to the Deglet Noor cultivar produced the greatest amount of pollen with 1250.98 and 1114.26 g on average for each year, produced during a late, short flowering period. Likewise, those palms with phenotypes similar to the Medjool cultivar produced the second-highest amount of pollen with 851.28 and 866.43 g on average for each year, produced during an early, long flowering period. Finally, an in vivo viability test through the fruit set percentage, revealed that the use of any of these four pollen sources would be suitable for the pollination of the recipient female cultivar Medjool, the most widely cultivated variety in Mexico. These results will allow date producers to select and propagate better pollen-producing male palms.
    Keywords Phoenix dactylifera ; agriculture ; cultivars ; females ; fruit set ; males ; phenotype ; pollen ; pollen productivity ; pollination ; seedlings ; viability assays ; vigor ; Mexico
    Language English
    Dates of publication 2022-0818
    Publishing place Multidisciplinary Digital Publishing Institute
    Document type Article
    ZDB-ID 2651678-0
    ISSN 2077-0472
    ISSN 2077-0472
    DOI 10.3390/agriculture12081248
    Database NAL-Catalogue (AGRICOLA)

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