Synthesis and characterization of the fluorescent products derived from malonaldehyde and amino acids

Chio, K. S.; Tappel, Al L.

doi:10.1021/bi00835a019

Cited by 514 publications

(194 citation statements)

References 21 publications

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“…10). The increase occurs with an excitation maximum of 370 nm and an emission maximum of 450 nm, similar to the spectrum of lipofuscin or "age" pigments found in vivo, which are believed to be substituted I-amino-3-iminopropene structures, formed when auto-oxidized lipids react with protein (15,27,28).…”

Section: Mateirials and Methodssupporting

confidence: 63%

“…Studies on the oxidation of lipid-protein mixtures have demonstrated that one type of effect on the protein is the covalent binding of lipid oxidation products, some of which can result in fluorescent substituents, including crosslinks (15,27,28). This reaction also occurs in our system, as shown by the increase in protein fluorescence with increasing time of oxidation (Fig.…”

Section: Discussionmentioning

confidence: 72%

See 1 more Smart Citation

Oxygen-mediated heterogeneity of apo-low-density lipoprotein.

Schuh¹,

Fairclough²,

Haschemeyer³

1978

Proc. Natl. Acad. Sci. U.S.A.

245

121

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Mild oxidation of human serum low-density lipoprotein (LDL) converts the apoprotein from a nearly homogeneous component of high apparent molecular weight to a mixture of apparently lower mo ecular weight polypeptide components, as characterized by sodium dodecyl sulfate/ polyacrylamide gel electrophoresis. This protein alteration, which correlates temporally with increases in the formation of lipid oxidation products and in the fluorescence of the apoprotein, is markedly reduced when oxygen is excluded or when EDTA or the free-radical-scavenging antioxidants, butylated hydroxytoluene or propyl gallate, are added. The conversion thus appears to be due to a reaction between the protein moiety and auto-oxidizing lipid. The presence of the antibacterial agent sodium azide markedly accelerates the oxidation, suggesting that it should only be used with caution in lipid-containing solutions. Structural and functional characterization of serum lipoproteins has received attention because molecular or metabolic abnormalities associated with this class of molecules might be significant in the development of atherosclerosis (1). The lowdensity lipoprotein fraction (LDL) has been of particular interest because of its apparent role in atherogenesis. Such a role is indicated by a correlation between high serum levels of LDL and clinical atherosclerosis (2), as well as the accelerated atherosclerosis in patients who have an inherited abnormality in LDL catabolism (familial hypercholesterolemia) (3). LDL is catabolized after it is bound through its protein moiety (apo-B or apo-LDL) to a cell-surface receptor (4).Although characterization of the apoprotein of LDL has been difficult (5), studies on the lipid moiety appear to be less controversial. LDL contains a large proportion of unsaturated lipids (somewhat variable on diet) (6) and is unique among the serum lipoproteins in its susceptibility for undergoing auto-oxidation in vitro (7-9). This finding has led some authors to speculate that such auto-oxidation plays a role in atherogenesis (7,10,11). Although structural (7-13), spectrophotometric (9,13,14), and lipid compositional (8, 11) changes in LDL have been observed upon oxidation, its polypeptide chain has not been characterized. Model studies with lipid-protein mixtures have shown that oxidized lipid can lead to major modification of protein components; such modifications include crosslinking (15), polypeptide scission (16), and loss of amino acids (17, 18). It thus seems possible that some of the difficulties encountered in characterizing apo-B are associated with partial oxidation of LDL during purification and/or storage. The observation that plasma lipids from human subjects contain significant diene conjugation (an early manifestation of lipid auto-oxidation) suggests that oxidation of LDL can be initiated in vivo (19).We show here that mild oxidation of LDL in vitro results in altering the sodium dodecyl sulfate (NaDodSO4)-apoprotein electrophoretic pattern from a single major band of low mobility into nume...

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Section: Mateirials and Methodssupporting

confidence: 63%

Section: Discussionmentioning

confidence: 72%

Oxygen-mediated heterogeneity of apo-low-density lipoprotein.

Schuh¹,

Fairclough²,

Haschemeyer³

1978

Proc. Natl. Acad. Sci. U.S.A.

245

121

View full text Add to dashboard Cite

show abstract

“…7 -9) These autoxidation products, both LAHPO and SP, are deleterious to animals. It is considered that their toxic effects on animals are due to the sum total of many kinds of products,1°) such as LAHP0,11) hydroperoxyl alkenals,12) aldehyde compounds,13-15) malonaldehyde (MA), 16) and so forth. These toxicants are contained in our daily food, although their amounts may not be high.…”

mentioning

confidence: 99%

Some Analytical Observations of Autoxidation Products of Linoleic Acid and Their Thiobarbituric Acid Reactive Substances

Kanazawa¹,

Danno²,

Natake³

1983

Agricultural and Biological Chemistry

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“…Keratin and Elastin molecules of connective tissue emit auto fluorescent light at 430 nm. Both molecules are rare in intervertebral discs and do not contribute to disc auto florescence [2,5,8,9] All collagen molecules in all tissues emit auto fluorescent light under UV irradiation [7,13,20,25]. Other molecules-particularly hemoglobin-extinct the auto fluorescence [12].…”

Section: The Origin Of Auto Fluorescencementioning

confidence: 99%

Auto fluorescence of intervertebral disc tissue: a new diagnostic tool

et al. 2006

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The paper reports on auto fluorescence phenomena of inter-vertebral human discs. It systematically investigates the auto fluorescence effects of ex vivo disc specimen and reports on surgical cases to demonstrate the potential value of the new method. The paper offers biologic explanations of the phenomenon and discusses the potential value of the UV auto fluorescence technique as a diagnostic tool. Intraand postoperative observations are made by a surgical microscope with an integrated UV light source. Quantitative measurements were carried out using a photon counter and a spectrometer ex vivo. The auto fluorescence phenomenon allows the differentiation of traumatized and degenerated disc tissue intraoperatively in some cases, it allows the differentiation of bony and collagen endplate in cervical disc surgery. The source of the auto fluorescent light emission are amino acids of the collagen molecules. The proteoglycan components and the liquid components of the disc do not show relevant auto fluorescence. Emission wavelength of disc material is equivalent to color perception. It differs due to different collagen composition of the intervertebral disc components from yellow-green to blue-green and can be visualized in situ by naked eye.UV-auto fluorescence of inter-vertebral discs is a new clinical tool that has the potential to differentiate disc material from the anatomical surrounding, to distinguish between different fractions of the disc and to give information on the quality and status of the disc material. Since the technology has just emerged, it needs further investigations to quantify the clinical observations reported in this paper.

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Synthesis and characterization of the fluorescent products derived from malonaldehyde and amino acids

Cited by 514 publications

References 21 publications

Oxygen-mediated heterogeneity of apo-low-density lipoprotein.

Oxygen-mediated heterogeneity of apo-low-density lipoprotein.

Some Analytical Observations of Autoxidation Products of Linoleic Acid and Their Thiobarbituric Acid Reactive Substances

Auto fluorescence of intervertebral disc tissue: a new diagnostic tool

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