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1

McClintock, Dana E., Barry Starcher, Mark D. Eisner, et al. "Higher urine desmosine levels are associated with mortality in patients with acute lung injury." American Journal of Physiology-Lung Cellular and Molecular Physiology 291, no. 4 (2006): L566—L571. http://dx.doi.org/10.1152/ajplung.00457.2005.

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Desmosine is a stable breakdown product of elastin that can be reliably measured in urine samples. We tested the hypothesis that higher baseline urine desmosine would be associated with higher mortality in 579 of 861 patients included in the recent Acute Respiratory Distress Syndrome Network trial of lower tidal volume ventilation ( 1 ). We also correlated urine desmosine levels with indexes of disease severity. Finally, we assessed whether urine desmosine was lower in patients who received lower tidal volumes. Desmosine was measured by radioimmunoassay in urine samples from days 0, 1, and 3 o
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2

Starcher, Barry, and Marti Scott. "Fractionation of Urine to Allow Desmosine Analysis by Radioimmunoassay." Annals of Clinical Biochemistry: International Journal of Laboratory Medicine 29, no. 1 (1992): 72–78. http://dx.doi.org/10.1177/000456329202900111.

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The present study was designed to re-evaluate the radioimmunoassay for desmosine in urine, which is currently used as a measure of elastin metabolism. Using ion exchange chromatography, gel filtration and affinity chromatography it was shown that at least five other compounds in hydrolysates of human urine competed for desmosine in the RIA. Fractionating the urine prior to hydrolysis with acetone removed one of the major contaminants. The other contaminants could subsequently be removed by extracting the urine hydrolysate with a mixture of chloroform/ethanol (60:40). Samples from nine normal a
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3

Murakami, Yuko, Rina Suzuki, Hiroto Yanuma, et al. "Synthesis and LC-MS/MS analysis of desmosine-CH2, a potential internal standard for the degraded elastin biomarker desmosine." Org. Biomol. Chem. 12, no. 48 (2014): 9887–94. http://dx.doi.org/10.1039/c4ob01438c.

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4

Hirose, Mika, Reiko Yokoo, Daisuke Watanabe, Rina Suzuki, Miho Tanigawa, and Toyonobu Usuki. "Synthesis of Multi‐Deuterated Desmosine." ChemistrySelect 5, no. 13 (2020): 3843–46. http://dx.doi.org/10.1002/slct.202000507.

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5

Schräder, Christoph U., Andrea Heinz, Petra Majovsky, and Christian E. H. Schmelzer. "Fingerprinting Desmosine-Containing Elastin Peptides." Journal of The American Society for Mass Spectrometry 26, no. 5 (2015): 762–73. http://dx.doi.org/10.1007/s13361-014-1075-9.

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6

Pai, V., A. Guz, G. J. Phillips, N. T. Cooke, D. C. S. Hutchison, and T. D. Tetley. "Urinary desmosine, elastolysis, and lung disease." Metabolism 40, no. 2 (1991): 139–45. http://dx.doi.org/10.1016/0026-0495(91)90164-r.

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7

Janssen, Rob, Jef Serré, Ianthe Piscaer, et al. "Post hoc analysis of a randomised controlled trial: effect of vitamin D supplementation on circulating levels of desmosine in COPD." ERJ Open Research 6, no. 4 (2020): 00128–2019. http://dx.doi.org/10.1183/23120541.00128-2019.

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BackgroundVitamin D supplementation lowers exacerbation frequency in severe vitamin D-deficient patients with COPD. Data regarding the effect of vitamin D on elastin degradation are lacking. Based on the vitamin's anti-inflammatory properties, we hypothesised that vitamin D supplementation reduces elastin degradation, particularly in vitamin D-deficient COPD patients. We assessed the effect of vitamin D status and supplementation on elastin degradation by measuring plasma desmosine, a biomarker of elastin degradation.MethodsDesmosine was measured every 4 months in plasma of 142 vitamin D-naïve
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8

Sekhon, H. S., and W. M. Thurlbeck. "Lung growth in hypobaric normoxia, normobaric hypoxia, and hypobaric hypoxia in growing rats. I. Biochemistry." Journal of Applied Physiology 78, no. 1 (1995): 124–31. http://dx.doi.org/10.1152/jappl.1995.78.1.124.

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Adaptive changes in cellular and connective tissue components of the lung after chronic exposure to reduced ambient oxygen and/or pressure were studied. Four-week-old male Sprague-Dawley rats were randomly divided into five groups (n = 12 each): 1) general control, room air (GC); 2) hypobaric normoxic; 3) normobaric hypoxic; 4) hypobaric hypoxic; and 5) weight-matched control, restricted food intake (WMC; weight matched to hypobaric hypoxic animals). Lung growth (lung weight and DNA, RNA, protein, hydroxyproline, and desmosine contents) diminished in WMC compared with GC. Somatic growth decrea
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9

Zay, K., S. Loo, C. Xie, D. V. Devine, J. Wright та A. Churg. "Role of neutrophils and α1-antitrypsin in coal- and silica-induced connective tissue breakdown". American Journal of Physiology-Lung Cellular and Molecular Physiology 276, № 2 (1999): L269—L279. http://dx.doi.org/10.1152/ajplung.1999.276.2.l269.

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Mineral dusts produce emphysema, and administration of dust to rats results in the rapid appearance of desmosine and hydroxyproline in lavage fluid, confirming that dusts directly induce connective tissue breakdown. To examine the role of neutrophils and α1-antitrypsin (α1-AT) in this process, we instilled silica or coal into normal rats or rats that had been pretreated with antiserum against neutrophils. One day after dust exposure, lavage fluid neutrophils and desmosine and hydroxyproline levels were all elevated; treatment with antiserum against neutrophils reduced neutrophils by 75%, desmo
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10

TETLEY, T. D., G. J. PHILLIPS, A. GUZ, and B. FOX. "The Blotchy Mouse, Lung Desmosine, and Emphysema." Annals of the New York Academy of Sciences 624, no. 1 (1991): 358. http://dx.doi.org/10.1111/j.1749-6632.1991.tb17048.x.

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11

Guay, M., G. Lagace, and F. Lamy. "Photolysis and Ozonolysis of Desmosine and Elastolytic Peptides." Connective Tissue Research 14, no. 2 (1985): 89–107. http://dx.doi.org/10.3109/03008208509015016.

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12

Dhital, Basant, Philip Durlik, Pratikkumar Rathod, et al. "Ultraviolet radiation reduces desmosine cross-links in elastin." Biochemistry and Biophysics Reports 10 (July 2017): 172–77. http://dx.doi.org/10.1016/j.bbrep.2017.04.002.

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13

Leppert, Phyllis C., Shiu Yeh Yu, Stephen Keller, Joseph Cerreta, and Ines Mandl. "Decreased elastic fibers and desmosine content in incompetent cervix." American Journal of Obstetrics and Gynecology 157, no. 5 (1987): 1134–39. http://dx.doi.org/10.1016/s0002-9378(87)80277-6.

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14

Fill, J. A., J. T. Brandt, H. P. Wiedemann, et al. "Urinary desmosine as a biomarker in acute lung injury." Biomarkers 11, no. 1 (2006): 85–96. http://dx.doi.org/10.1080/13547500500343225.

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15

Sulaiman, Mazdida, Marie-Therese Martin, Mary Pais, A. Hamid A. Hadi, and Khalijah Awang. "ChemInform Abstract: Desmosine, an Artefact Alkaloid from Desmos dumosus." ChemInform 30, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199918205.

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16

Usuki, Toyonobu, Haruka Yamada, Takahiro Hayashi, et al. "Total synthesis of COPD biomarker desmosine that crosslinks elastin." Chemical Communications 48, no. 26 (2012): 3233. http://dx.doi.org/10.1039/c2cc17958j.

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17

Giummelly, Philippe, Bernard Botton, Raphaëlle Friot, Deddi Prima-Putra, and Jeffrey Atkinson. "Measurement of desmosine and isodesmosine by capillary zone electrophoresis." Journal of Chromatography A 710, no. 2 (1995): 357–60. http://dx.doi.org/10.1016/0021-9673(95)00487-4.

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18

Sabirin, Rahmaningsih Mara, Prasetyastuti, and Denny Agustiningsih. "Rosuvastatin Attenuated Elastic Fiber Degradation in Chronic Obstructive Pulmonary Disease Sprague-Dawley Rats." Jurnal Kedokteran Brawijaya 30, no. 3 (2019): 175. http://dx.doi.org/10.21776/ub.jkb.2019.030.03.2.

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<p>Chronic obstructive pulmonary disease (COPD) is an incurable disease which causes disability and death. The main pathogenesis of COPD is oxidative stress due to cigarette smoke which initiates various reactions and lead to lung elastic fibers destruction. Statins are known to have antioxidant effects and reduce mortality in COPD. We studied the effects of cigarette smoke exposure cessation and rosuvastatin on oxidative stress and the level of elastic fiber destruction in COPD model rats. Thirty 10-week old male Sprague-Dawley rats were divided into 2 groups: Control (n=6, did not rece
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19

AIKAWA, JUNICHIRO, HIROSHI MUNAKATA, MAMORU ISEMURA, and ZENSAKU YOSIZAWA. "Sulfated glycopeptides, containing desmosine and isodesmosine, isolated from porcine aorta." Tohoku Journal of Experimental Medicine 145, no. 2 (1985): 175–83. http://dx.doi.org/10.1620/tjem.145.175.

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20

Ma, Shuren, Yong Y. Lin, and Gerard M. Turino. "Measurements of Desmosine and Isodesmosine by Mass Spectrometry in COPD." Chest 131, no. 5 (2007): 1363–71. http://dx.doi.org/10.1378/chest.06-2251.

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21

Luisetti, M., J. Stolk, and P. Iadarola. "Desmosine, a biomarker for COPD: old and in the way." European Respiratory Journal 39, no. 4 (2012): 797–98. http://dx.doi.org/10.1183/09031936.00172911.

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22

Adgate, John L., Holly F. Reid, Robin Morris, et al. "Nitrogen Dioxide Exposure and Urinary Excretion of Hydroxyproline and Desmosine." Archives of Environmental Health: An International Journal 47, no. 5 (1992): 376–84. http://dx.doi.org/10.1080/00039896.1992.9938378.

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23

Cantor, Jerome, Arnulfo Ochoa, Shuren Ma, Xingjian Liu, and Gerard Turino. "Free Desmosine is a Sensitive Marker of Smoke-Induced Emphysema." Lung 196, no. 6 (2018): 659–63. http://dx.doi.org/10.1007/s00408-018-0163-1.

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24

Cumiskey, Wayne R., Edward D. Pagani, and Donald C. Bode. "Enrichment and analysis of desmosine and isodesmosine in biological fluids." Journal of Chromatography B: Biomedical Sciences and Applications 668, no. 2 (1995): 199–207. http://dx.doi.org/10.1016/0378-4347(95)00092-w.

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25

Myers, B. A., M. A. Dubick, R. D. Reynolds, and R. B. Rucker. "Effect of vitamin B-6 (pyridoxine) deficiency on lung elastin cross-linking in perinatal and weanling rat pups." Biochemical Journal 229, no. 1 (1985): 153–60. http://dx.doi.org/10.1042/bj2290153.

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Weanling and perinatal rats were rendered vitamin B-6 (pyridoxine)-deficient. The rat pups were nursed from vitamin B-6-deficient or -sufficient dams and were killed at day 15 after parturition. The weanling rats were fed vitamin B-6-deficient or -sufficient diets and were killed after 5 weeks of treatment. Lung elastin from the groups of rats was then studied with respect to its content of lysine-derived cross-linking amino acids. Lung lysyl oxidase activity was also measured. B-6 deficiency decreased the number of lysine residues in elastin that were converted into the cross-linking amino ac
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26

Low, R. B., W. S. Stirewalt, P. Hultgren, E. S. Low, and B. Starcher. "Changes in collagen and elastin in rabbit right-ventricular pressure overload." Biochemical Journal 263, no. 3 (1989): 709–13. http://dx.doi.org/10.1042/bj2630709.

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Collagen content, the ratio of collagen types I and III and elastin content were measured in 5-6- and 10-12-week-old rabbits with and without right-ventricular pressure overload. Significant and equivalent hypertrophy occurred in both age groups. A 2-day pressure overload caused a fall in collagen concentration below control levels in right-ventricular tissue from the older animals, but no change in the younger ones. A 2-week pressure overload in the older animals resulted in a rise in collagen concentration, a decreased ratio of type III to type I plus III [III/(I + III)] collagens, a fall in
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27

Mackey, K., M. C. Meyer, W. S. Stirewalt, B. C. Starcher, and M. K. McLaughlin. "Composition and mechanics of mesenteric resistance arteries from pregnant rats." American Journal of Physiology-Regulatory, Integrative and Comparative Physiology 263, no. 1 (1992): R2—R8. http://dx.doi.org/10.1152/ajpregu.1992.263.1.r2.

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We tested the hypothesis that the systemic resistance vasculature of the rat is remodeled during pregnancy as evidenced by significant alterations in the passive mechanical properties and extracellular matrix proteins in mesenteric arteries. Mechanical characteristics were determined for arteries from 20-day pregnant rats (n = 6) and age-matched controls (n = 5). Lumen diameter and wall thickness were measured in pressurized arteries (250-microns diameter) using a dimension analyzing system. Distensibility (the relative change in diameter per unit change in pressure) was less in the arteries f
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28

Afdhal, Nezam H., Andrew P. Keaveny, Steven B. Cohen, et al. "Urinary assays for desmosine and hydroxylysylpyridinoline in the detection of cirrhosis." Journal of Hepatology 27, no. 6 (1997): 993–1002. http://dx.doi.org/10.1016/s0168-8278(97)80142-0.

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29

Boutin, Michel, Carl Berthelette, François G. Gervais, et al. "High-Sensitivity NanoLC−MS/MS Analysis of Urinary Desmosine and Isodesmosine." Analytical Chemistry 81, no. 5 (2009): 1881–87. http://dx.doi.org/10.1021/ac801745d.

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30

Laguna, Theresa A., Brandie D. Wagner, Heidi K. Luckey, et al. "Sputum Desmosine During Hospital Admission for Pulmonary Exacerbation in Cystic Fibrosis." Chest 136, no. 6 (2009): 1561–68. http://dx.doi.org/10.1378/chest.09-0217.

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31

Minkin, Ruth, Gagangeet Sandhu, Horiana Grosu, et al. "Desmosine and Isodesmosine as a Novel Biomarker for Pulmonary Arterial Hypertension." American Journal of Therapeutics 24, no. 4 (2017): e399-e404. http://dx.doi.org/10.1097/mjt.0000000000000260.

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32

Tanaka, Nao, Manami Kurita, Yuko Murakami, and Toyonobu Usuki. "Chichibabin and IsoChichibabin Pyridinium Syntheses of Isodesmosine, Desmosine, and their Derivatives." European Journal of Organic Chemistry 2018, no. 43 (2018): 6002–9. http://dx.doi.org/10.1002/ejoc.201801156.

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33

FIORENZA, D., S. VIGLIO, A. LUPI, et al. "Urinary desmosine excretion in acute exacerbations of COPD: a preliminary report." Respiratory Medicine 96, no. 2 (2002): 110–14. http://dx.doi.org/10.1053/rmed.2001.1224.

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34

Stone, P. J., E. C. Lucey, G. L. Snider, and C. Franzblau. "Effect of diet on urinary excretion of desmosine and hydroxylysyl pyridinoline." American Journal of Respiratory and Critical Care Medicine 149, no. 1 (1994): 174–77. http://dx.doi.org/10.1164/ajrccm.149.1.8111578.

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35

Starcher, Barry, Michael Green, and Marti Scott. "Measurement of Urinary Desmosine as an Indicator of Acute Pulmonary Disease." Respiration 62, no. 5 (1995): 252–57. http://dx.doi.org/10.1159/000196458.

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36

Sato, Takaji, Takashi Kajikuri, Yoshihiro Saito, Masahiko Chikuma, and Sonoko Nagai. "Determination of desmosine in bronchoalveolar lavage fluids by time-resolved fluoroimmunoassay." Clinica Chimica Acta 387, no. 1-2 (2008): 113–19. http://dx.doi.org/10.1016/j.cca.2007.09.015.

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37

Stone, Phillip J., Julianne Bryan-Rhadfi, Edgar C. Lucey, et al. "Measurement of Urinary Desmosine by Isotope Dilution and High Performance Liquid Chromatography: Correlation between Elastase-induced Air-Space Enlargement in the Hamster and Elevation of Urinary Desmosine." American Review of Respiratory Disease 144, no. 2 (1991): 284–90. http://dx.doi.org/10.1164/ajrccm/144.2.284.

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38

Iskandar, Zaid, Ify Mordi, Jeffrey T. J. Huang, et al. "PLASMA DESMOSINE, AN ELASTIN DEGRADATION PRODUCT, PREDICTS OUTCOMES IN AT RISK POPULATIONS." Journal of the American College of Cardiology 73, no. 9 (2019): 1805. http://dx.doi.org/10.1016/s0735-1097(19)32411-8.

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39

LOW, R., P. HULTGREN, B. STARCHER, W. STIREWALT, B. MACLEOD, and E. LOW. "Collagen and desmosine in three models of rabbit right ventricular pressure overload." Journal of Molecular and Cellular Cardiology 19 (1987): S53. http://dx.doi.org/10.1016/s0022-2828(87)80783-6.

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40

OSAKABE, Toru, Eiji USAMI, Akira SATO, Shigeru SASAKI, Tetsuo WATANABE, and Yoshiyuki SEYAMA. "Characteristic Change of Urinary Elastin Peptides and Desmosine in the Aortic Aneurysm." Biological & Pharmaceutical Bulletin 22, no. 8 (1999): 854–57. http://dx.doi.org/10.1248/bpb.22.854.

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41

Laguna, Theresa A., Brandie D. Wagner, Barry Starcher, et al. "Urinary desmosine: A biomarker of structural lung injury during CF pulmonary exacerbation." Pediatric Pulmonology 47, no. 9 (2012): 856–63. http://dx.doi.org/10.1002/ppul.22525.

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42

Usuki, Toyonobu, Haruka Yamada, Takahiro Hayashi, et al. "ChemInform Abstract: Total Synthesis of COPD Biomarker Desmosine (I) that Crosslinks Elastin." ChemInform 43, no. 29 (2012): no. http://dx.doi.org/10.1002/chin.201229212.

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43

Rathod, Pratikkumar, Manjeet Kaur, Hsin-Pin Ho, et al. "Quantification of desmosine and isodesmosine using MALDI-ion trap tandem mass spectrometry." Analytical and Bioanalytical Chemistry 410, no. 26 (2018): 6881–89. http://dx.doi.org/10.1007/s00216-018-1288-z.

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44

Salomoni, M., M. Muda, E. Zuccato, and E. Mussini. "High-performance liquid chromatographic determination of desmosine and isodesmosine after phenylisothiocyanate derivatization." Journal of Chromatography B: Biomedical Sciences and Applications 572, no. 1-2 (1991): 312–16. http://dx.doi.org/10.1016/0378-4347(91)80496-y.

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45

Piscaer, Ianthe, Jody M. W. van den Ouweland, Kristina Vermeersch, et al. "Low Vitamin K Status Is Associated with Increased Elastin Degradation in Chronic Obstructive Pulmonary Disease." Journal of Clinical Medicine 8, no. 8 (2019): 1116. http://dx.doi.org/10.3390/jcm8081116.

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Elastin degradation is accelerated in chronic obstructive pulmonary disease (COPD) and is partially regulated by Matrix Gla Protein (MGP), via a vitamin K-dependent pathway. The aim was to assess vitamin K status in COPD as well as associations between vitamin K status, elastin degradation, lung function parameters and mortality. A total of 192 COPD patients and 186 age-matched controls were included. In addition to this, 290 COPD patients from a second independent longitudinal cohort were also included. Vitamin K status was assessed by measuring plasma inactive MGP levels and rates of elastin
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46

Rabinovich, Roberto A., Bruce E. Miller, Karolina Wrobel, et al. "Circulating desmosine levels do not predict emphysema progression but are associated with cardiovascular risk and mortality in COPD." European Respiratory Journal 47, no. 5 (2016): 1365–73. http://dx.doi.org/10.1183/13993003.01824-2015.

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Elastin degradation is a key feature of emphysema and may have a role in the pathogenesis of atherosclerosis associated with chronic obstructive pulmonary disease (COPD). Circulating desmosine is a specific biomarker of elastin degradation. We investigated the association between plasma desmosine (pDES) and emphysema severity/progression, coronary artery calcium score (CACS) and mortality.pDES was measured in 1177 COPD patients and 110 healthy control subjects from two independent cohorts. Emphysema was assessed on chest computed tomography scans. Aortic arterial stiffness was measured as the
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47

Jules-Elysee, Kethy M., Sarah E. Wilfred, Stavros G. Memtsoudis, et al. "Steroid Modulation of Cytokine Release and Desmosine Levels in Bilateral Total Knee Replacement." Journal of Bone & Joint Surgery 94, no. 23 (2012): 2120–27. http://dx.doi.org/10.2106/jbjs.k.00995.

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48

Ongay, Sara, Marijke Sikma, Peter Horvatovich, et al. "Free Urinary Desmosine and Isodesmosine as COPD Biomarkers: The Relevance of Confounding Factors." Chronic Obstructive Pulmonary Diseases: Journal of the COPD Foundation 3, no. 2 (2016): 560–69. http://dx.doi.org/10.15326/jcopdf.3.2.2015.0159.

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49

DAVRIL, MONIQUE, MIREILLE GUAY, KIA-KI HAN, and FRANCOIS LAMY. "Photolysis and ozonolysis of (iso) desmosine-containing crosslinked peptides from porcine aorta elastin." International Journal of Peptide and Protein Research 29, no. 1 (2009): 68–77. http://dx.doi.org/10.1111/j.1399-3011.1987.tb02231.x.

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50

Viglio, S., P. Iadarola, A. Lupi, et al. "MEKC of desmosine and isodesmosine in urine of chronic destructive lung disease patients." European Respiratory Journal 15, no. 6 (2000): 1039. http://dx.doi.org/10.1034/j.1399-3003.2000.01511.x.

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