Chemical Research in Toxicology
Article
Funding
atherogenic oxidized phospholipids promotes macrophage foam cell
formation via the scavenger receptor CD36 and is enriched in
atherosclerotic lesions. J. Biol. Chem. 277, 38517−38523.
This work was supported by NIH Grants EY016813 and
GM021249 to R.G.S.
(10) Gu, X., Sun, M., Gugiu, B., Hazen, S., Crabb, J. W., and
Notes
Salomon, R. G. (2003) Oxidatively truncated docosahexaenoate
phospholipids: total synthesis, generation, and Peptide adduction
chemistry. J. Org. Chem. 68, 3749−3761.
(11) Barrera, G. (2012) Oxidative stress and lipid peroxidation
products in cancer progression and therapy. ISRN Oncol. 2012, 1.
The authors declare no competing financial interest.
ABBREVIATIONS
■
ABTS, 2,2-azino-bis (3-ethylbenzthiazoline-6-sulfonic acid
diammonium salt; AMD, age-related macular degeneration;
BSA, bovine serum albumin; CEP, 2-(ω-carboxyethyl)pyrrole;
CID, collision-induced dissociation; DHA, docosahexaenoic
acid; DHA-PC, 1-palmityl-2-docosahexaenoyl-sn-glycero-3-
phosphocholine; DPPE, 1,2-dipalmitoyl-sn-glycero-3-phos-
phoethanolamine; ELISA, enzyme-linked immunosorbent
assay; EP, ethanolamine phospholipid; ETN, ethanolamine;
(12) Arneson, K. O., and Roberts, L. J. (2007) Measurement of
Products of Docosahexaenoic Acid Peroxidation, Neuroprostanes, and
Neurofurans. Methods Enzymol. 433, 127−143.
(13) Sayre, L. M., Sha, W., Xu, G., Kaur, K., Nadkarni, D.,
Subbanagounder, G., and Salomon, R. G. (1996) Immunochemical
evidence supporting 2-pentylpyrrole formation on proteins exposed to
4-hydroxy-2-nonenal. Chem. Res. Toxicol. 9, 1194−1201.
(14) Kaur, K., Salomon, R. G., O’Neil, J., and Hoff, H. F. (1997)
Carboxyalkyl)pyrroles in human plasma and oxidized low-density
4-HNE, 4-hydroxy-2-nonenal; HODA, 9-hydroxy-12-oxodo-
lipoproteins. Chem. Res. Toxicol. 10, 1387−1396.
dec-10-enoic acid; HOHA, 4-hydroxy-7-oxo-hept-5-eonic acid;
HOHA-PC, 1-palmityl-2-(4-hydroxy-7-oxo-5-heptenoyl)-sn-
glycero-3-phosphatidylcholine; HOOA, 5-hydroxy-8-oxooct-6-
enoic acid; HSA, human serum albumin; HUVECs, human
umbilical vein endothelial cells; KLH, keyhole limpet
hemocyanin; KODA, 9-keto-12-oxododec-10-enoic acid;
KOHA, 4-keto-7-oxohept-5-enoic acid; KOOA, 5-keto-8-
oxooct-6-enoic acid; MRM, multiple reaction monitoring;
OHdiA, 4-oxo-heptanedioic acid; OHdiA 2-hydroxyethylamide,
(
15) Narayan, B., Miyashita, K., and Hosakawa, M. (2006)
Physiological Effects of Eicosapentaenoic Acid (EPA) and Docosahex-
aenoic Acid (DHA)A Review. Food Rev. Int. 22, 291−307.
(16) SanGiovanni, J. P., and Chew, E. Y. (2005) The role of omega-3
long-chain polyunsaturated fatty acids in health and disease of the
retina. Prog. Retinal Eye Res. 24, 87−138.
(17) Gu, X., Meer, S. G., Miyagi, M., Rayborn, M. E., Hollyfield, J. G.,
Crabb, J. W., and Salomon, R. G. (2003) Carboxyethylpyrrole protein
adducts and autoantibodies, biomarkers for age-related macular
degeneration. J. Biol. Chem. 278, 42027−42035.
7-((2-hydroxyethyl)amino)-4,7-dioxoheptanoic acid; OHdiA-
(18) Wang, H., Guo, J., West, X. Z., Bid, H. K., Lu, L., Hong, L., Jang,
diPFB, bis(perfluorophenyl) 4-oxoheptanedioate; 4-ONE, 4-
oxo-2-nonenal; oxLDL, oxidized low-density lipoprotein; PFB-
Br, pentafluorobenzyl bromide; PP, 2-pentylpyrrole; PUFA,
polyunsaturated fatty acid; SICs, selected ion chromatograms;
SUV, small unilammelar vesicle; TLR, Toll-like receptor
G. F., Zhang, L., Crabb, J. W., Linetsky, M., and Salomon, R. G. (2014)
Detection and biological activities of carboxyethylpyrrole ethanol-
amine phospholipids (CEP-EPs). Chem. Res. Toxicol. 27, 2015−2022.
(19) West, X. Z., Malinin, N. L., Merkulova, A. A., Tischenko, M.,
Kerr, B. A., Borden, E. C., Podrez, E. A., Salomon, R. G., and Byzova,
T. V. (2010) Oxidative stress induces angiogenesis by activating TLR2
with novel endogenous ligands. Nature 467, 972−976.
REFERENCES
■
(20) Zhu, X., and Sayre, L. M. (2007) Long-lived 4-oxo-2-enal-
(
1) Catala, A. (2006) An overview of lipid peroxidation with
emphasis in outer segments of photoreceptors and the chemilumi-
derived apparent lysine michael adducts are actually the isomeric 4-
ketoamides. Chem. Res. Toxicol. 20, 165−170.
nescence assay. Int. J. Biochem. Cell Biol. 38, 1482−1495.
(21) Williams, M. V., Wishnok, J. S., and Tannenbaum, S. R. (2007)
(
2) Lin, D., Lee, H. G., Liu, Q., Perry, G., Smith, M. A., and Sayre, L.
Covalent adducts arising from the decomposition products of lipid
hydroperoxides in the presence of cytochrome c. Chem. Res. Toxicol.
M. (2005) 4-Oxo-2-nonenal is both more neurotoxic and more protein
reactive than 4-hydroxy-2-nonenal. Chem. Res. Toxicol. 18, 1219−1231.
2
(
(
0, 767−775.
22) Szapacs, M. E., Kim, H. Y., Porter, N. A., and Liebler, D. C.
2008) Identification of proteins adducted by lipid peroxidation
(
3) Zhu, X., Tang, X., Anderson, V. E., and Sayre, L. M. (2009) Mass
spectrometric characterization of protein modification by the products
of nonenzymatic oxidation of linoleic acid. Chem. Res. Toxicol. 22,
products in plasma and modifications of apolipoprotein A1 with a
1
(
386−1397.
novel biotinylated phospholipid probe. J. Proteome Res. 7, 4237−4246.
4) Sayre, L. M., Lin, D., Yuan, Q., Zhu, X., and Tang, X. (2006)
(23) Li, H. (2011) Syntheses and Immunological Detection of
Protein adducts generated from products of lipid oxidation: focus on
Oxidized Lipid-Derived Protein and Phosphatidylethanolamine
Modifications, in Chemistry p 155, Case Western Reserve University,
Cleveland, OH.
(24) Padwa, A., Rashatasakhon, P., and Rose, M. (2003) Triflic
anhydride mediated cyclization of 5-hydroxy-substituted pyrrolidi-
nones for the preparation of alpha-trifluoromethylsulfonamido furans.
J. Org. Chem. 68, 5139−5146.
(25) Guichardant, M., Taibi-Tronche, P., Fay, L. B., and Lagarde, M.
(1998) Covalent modifications of aminophospholipids by 4-hydrox-
ynonenal. Free Radical Biol. Med. 25, 1049−1056.
(26) Li, W., Laird, J. M., Lu, L., Roychowdhury, S., Nagy, L. E., Zhou,
R., Crabb, J. W., and Salomon, R. G. (2009) Isolevuglandins covalently
modify phosphatidylethanolamines in vivo: detection and quantitative
analysis of hydroxylactam adducts. Free Radical Biol. Med. 47, 1539−
1552.
(27) Sullivan, C. B., Matafonova, E., Roberts, L. J., 2nd, Amarnath, V.,
and Davies, S. S. (2010) Isoketals form cytotoxic phosphatidylethanol-
amine adducts in cells. J. Lipid Res. 51, 999−1009.
(28) Wang, H., Linetsky, M., Guo, J., Choi, J., Hong, L., Chamberlain,
A. S., Howell, S. J., Howes, A. M., and Salomon, R. G. (2015) 4-
HNE and one. Drug Metab. Rev. 38, 651−675.
(
5) Halliwell, B., and Chirico, S. (1993) Lipid peroxidation: its
mechanism, measurement, and significance. Am. J. Clin. Nutr. 57,
15S−724S discussion 724S−725S..
6) Catala, A. (2009) Lipid peroxidation of membrane phospholipids
7
(
generates hydroxy-alkenals and oxidized phospholipids active in
physiological and/or pathological conditions. Chem. Phys. Lipids 157,
1
(
(
−11.
7) Sun, M., Deng, Y., Batyreva, E., Sha, W., and Salomon, R. G.
2002) Novel bioactive phospholipids: practical total syntheses of
products from the oxidation of arachidonic and linoleic esters of 2-
lysophosphatidylcholine(1). J. Org. Chem. 67, 3575−3584.
(
8) Podrez, E. A., Poliakov, E., Shen, Z., Zhang, R., Deng, Y., Sun, M.,
Finton, P. J., Shan, L., Gugiu, B., Fox, P. L., Hoff, H. F., Salomon, R.
G., and Hazen, S. L. (2002) Identification of a novel family of oxidized
phospholipids that serve as ligands for the macrophage scavenger
receptor CD36. J. Biol. Chem. 277, 38503−38516.
(
9) Podrez, E. A., Poliakov, E., Shen, Z., Zhang, R., Deng, Y., Sun, M.,
Finton, P. J., Shan, L., Febbraio, M., Hajjar, D. P., Silverstein, R. L.,
Hoff, H. F., Salomon, R. G., and Hazen, S. L. (2002) A novel family of
M
Chem. Res. Toxicol. XXXX, XXX, XXX−XXX