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Chemical Compound Review

ISODESMOSINE     2-amino-6-[6-(4-amino-4- carboxy-butyl)-3,5...

Synonyms: Iso-desmosin, CHEBI:64366, HMDB00739, SureCN12707032, AC1L22JB, ...
 
 
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Disease relevance of ISODESMOSINE

 

High impact information on ISODESMOSINE

  • Desmosine and isodesmosine, cross-linking compounds associated with mature elastin, were found in hydrolysates of the shell membrane, confirming the necessity for lysyl oxidase in its biosynthesis [4].
  • Amino acid analyses of both elastin preparations indicated that the values for desmosine and isodesmosine were reduced in Marfan cases to approximately one-half of the control values [5].
  • The detection and quantitation of free desmosine and isodesmosine in human urine and their peptide-bound forms in sputum [6].
  • The DESP/desmosine (DES) and IDP/isodesmosine (IDE) ratios in aorta elastin were higher than in other tissues [7].
  • We conclude that lung elastin is the most likely source of the increased DES and IDES in CF [8].
 

Chemical compound and disease context of ISODESMOSINE

 

Biological context of ISODESMOSINE

  • For the gravid subjects as a group and also for each subject, the mean values for urinary DES, IDES, HP, and HP/LP during the first 6 weeks postpartum were significantly greater than the mean baseline values beginning 27 weeks postpartum [12].
  • We measured the urinary excretion of specific amino acid markers for mature elastin (desmosine [DES] and isodesmosine [IDES]) and fibrillar collagen (hydroxylysyl pyridinoline [HP] and lysyl pyridinoline [LP]) before and after parturition in three gravid subjects [12].
  • 1. Desmosine and isodesmosine were separated by ion-exchange and paper chromatography, after acid hydrolysis of purified elastin from beef ligamentum nuchae [13].
  • Intestinal absorption of desmosine and isodesmosine was investigated in several animal species [14].
  • Comparing amino acid compositions of eggshells collected following oviposition with those collected from the same clutch after hatching reveals similarities among all eggshells except those of Eumeces from Michigan which lack desmosine and isodesmosine [15].
 

Anatomical context of ISODESMOSINE

 

Associations of ISODESMOSINE with other chemical compounds

 

Gene context of ISODESMOSINE

  • Elastin contains a number of cross-linking amino acid residues such as desmosine and isodesmosine which are primarily hydrophobic in character, but have a positively charged pyridinium ring [25].
  • These are covalently cross-linked to form insoluble elastin by formation of desmosine and isodesmosine, catalysed by the enzyme lysyl oxidase [26].
  • All the data presented are consistent with the scheme proposed for the formation of desmosine and isodesmosine cross-links of elastin by Gerber & Anwar [(1975) Biochem. J. 149, 685--695] [27].
  • There was a significant reduction of both DES and IDES in dilated segments of varicose veins (P < 0.05 vs normal veins and nondilated segments); the ratio of elastin to collagen was lower in varicose than normal veins (P < 0.05), and this reduction was most significant in the dilated segments (P < 0.01 vs normal veins) [10].
  • Also found were marked decreases in the aorta contents of desmosine and isodesmosine, which are cross-linking amino acids present only in the elastin [28].
 

Analytical, diagnostic and therapeutic context of ISODESMOSINE

  • Urine specimens from 20 patients with SSc and 22 controls were assessed for DES, IDES, HP, and LP using high performance liquid chromatography and ultraviolet absorption spectroscopy, in combination with an isotope dilution technique in which the urine specimen was spiked with isotopically labeled cross-link amino acids [1].
  • We developed a direct and one-injection HPLC method to measure Pyr, Dpyr, Des, Isodes, and Pen in the hydrolysate of human yellow ligament [29].
  • Determination of desmosine, isodesmosine, and other amino acids by liquid chromatography with electrochemical detection following precolumn derivatization with naphthalenedialdehyde/cyanide [18].
  • The desmosine fraction could be resolved into seven compounds and the isodesmosine into four by paper chromatography [13].
  • Desmosine and isodesmosine as cross-links in the hinge-ligament protein of bivalves. 3,3'-Methylenebistyrosine as an artefact [30].

References

  1. Cross-linked elastin and collagen degradation products in the urine of patients with scleroderma. Stone, P.J., Korn, J.H., North, H., Lally, E.V., Miller, L.C., Tucker, L.B., Strongwater, S., Snider, G.L., Franzblau, C. Arthritis Rheum. (1995) [Pubmed]
  2. Urinary assays for desmosine and hydroxylysylpyridinoline in the detection of cirrhosis. Afdhal, N.H., Keaveny, A.P., Cohen, S.B., Nunes, D.P., Maldonado, N., O'Brien, M., Stone, P.J. J. Hepatol. (1997) [Pubmed]
  3. Distribution of elastin in hamsters and the turnover rates of different elastin pools. Stone, P.J., Lucey, E.C., Snider, G.L., Franzblau, C. Proc. Soc. Exp. Biol. Med. (1997) [Pubmed]
  4. Localization of lysyl oxidase in hen oviduct: implications in egg shell membrane formation and composition. Harris, E.D., Blount, J.E., Leach, R.M. Science (1980) [Pubmed]
  5. Marfan syndrome. Demonstration of abnormal elastin in aorta. Abraham, P.A., Perejda, A.J., Carnes, W.H., Uitto, J. J. Clin. Invest. (1982) [Pubmed]
  6. The detection and quantitation of free desmosine and isodesmosine in human urine and their peptide-bound forms in sputum. Ma, S., Lieberman, S., Turino, G.M., Lin, Y.Y. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  7. Two new elastin cross-links having pyridine skeleton. Implication of ammonia in elastin cross-linking in vivo. Umeda, H., Takeuchi, M., Suyama, K. J. Biol. Chem. (2001) [Pubmed]
  8. Elastin and collagen degradation products in urine of patients with cystic fibrosis. Stone, P.J., Konstan, M.W., Berger, M., Dorkin, H.L., Franzblau, C., Snider, G.L. Am. J. Respir. Crit. Care Med. (1995) [Pubmed]
  9. Biochemical markers of upper esophageal sphincter compliance in patients with Zenker's diverticulum. Venturi, M., Bonavina, L., Colombo, L., Antoniazzi, L., Bruno, A., Mussini, E., Peracchia, A. J. Surg. Res. (1997) [Pubmed]
  10. Biochemical assay of collagen and elastin in the normal and varicose vein wall. Venturi, M., Bonavina, L., Annoni, F., Colombo, L., Butera, C., Peracchia, A., Mussini, E. J. Surg. Res. (1996) [Pubmed]
  11. Measurement of cross-linked elastin synthesis in bleomycin-induced pulmonary fibrosis using a highly sensitive assay for desmosine and isodesmosine. Cantor, J.O., Osman, M., Keller, S., Cerreta, J.M., Mandl, I., Turino, G.M. J. Lab. Clin. Med. (1984) [Pubmed]
  12. Increase in urinary desmosine and pyridinoline during postpartum involution of the uterus in humans. Stone, P.J., Franzblau, C. Proc. Soc. Exp. Biol. Med. (1995) [Pubmed]
  13. Photolysis of desmosine and isodesmosine by ultraviolet light. Baurain, R., Larochelle, J.F., Lamy, F. Eur. J. Biochem. (1976) [Pubmed]
  14. Studies on the absorption of desmosine and isodesmosine. Starcher, B.C., Goldstein, R.A. J. Lab. Clin. Med. (1979) [Pubmed]
  15. External incubation alters the composition of squamate eggshells. Cox, D.L., Koob, T.J., Mecham, R.P., Sexton, O.J. Comp. Biochem. Physiol., B (1984) [Pubmed]
  16. The smooth muscle cell. III. Elastin synthesis in arterial smooth muscle cell culture. Narayanan, A.S., Sandberg, L.B., Ross, R., Layman, D.L. J. Cell Biol. (1976) [Pubmed]
  17. Alteration of elastin in aorta from diabetics. Tanno, T., Yoshinaga, K., Sato, T. Atherosclerosis (1993) [Pubmed]
  18. Determination of desmosine, isodesmosine, and other amino acids by liquid chromatography with electrochemical detection following precolumn derivatization with naphthalenedialdehyde/cyanide. Lunte, S.M., Mohabbat, T., Wong, O.S., Kuwana, T. Anal. Biochem. (1989) [Pubmed]
  19. Mature bovine Descemet's membrane contains desmosine and isodesmosine. Heathcote, J.G., Eyre, D.R., Gross, J. Biochem. Biophys. Res. Commun. (1982) [Pubmed]
  20. Elastin and collagen degradation products in urine of smokers with and without chronic obstructive pulmonary disease. Stone, P.J., Gottlieb, D.J., O'Connor, G.T., Ciccolella, D.E., Breuer, R., Bryan-Rhadfi, J., Shaw, H.A., Franzblau, C., Snider, G.L. Am. J. Respir. Crit. Care Med. (1995) [Pubmed]
  21. Temporal regulation of extracellular matrix components in transition from compensatory hypertrophy to decompensatory heart failure. Mujumdar, V.S., Tyagi, S.C. J. Hypertens. (1999) [Pubmed]
  22. The changes in crosslink contents in tissues after formalin fixation. Abe, M., Takahashi, M., Horiuchi, K., Nagano, A. Anal. Biochem. (2003) [Pubmed]
  23. Guanidination of the lysine residues present in fibrous elastin and in soluble elastin peptides. Guay, M., Lamy, F. Connect. Tissue Res. (1981) [Pubmed]
  24. Elevation of histidinoalanine in calcified human aortas. Fujimoto, D., Yu, S.Y. Biochem. Int. (1984) [Pubmed]
  25. Reactivity of human leukocyte elastase and porcine pancreatic elastase toward peptide 4-nitroanilides containing model desmosine residues. Evidence that human leukocyte elastase is selective for cross-linked regions of elastin. Yasutake, A., Powers, J.C. Biochemistry (1981) [Pubmed]
  26. Detection of elastin in the human fetal membranes: proposed molecular basis for elasticity. Hieber, A.D., Corcino, D., Motosue, J., Sandberg, L.B., Roos, P.J., Yu, S.Y., Csiszar, K., Kagan, H.M., Boyd, C.D., Bryant-Greenwood, G.D. Placenta (1997) [Pubmed]
  27. Amino acid sequences C-terminal to the cross-links in bovine elastin. Baig, K.M., Vlaovic, M., Anwar, R.A. Biochem. J. (1980) [Pubmed]
  28. Enhancement of aortic cholesterol deposition by dietary linoleic acid in cholesterol-fed mice: an animal model for primary screening of antiatherosclerotic agents. Yamaguchi, Y., Kitagawa, S., Imaizumi, N., Kunitomo, M., Fujiwara, M. Journal of pharmacological and toxicological methods. (1993) [Pubmed]
  29. Direct detection of crosslinks of collagen and elastin in the hydrolysates of human yellow ligament using single-column high performance liquid chromatography. Chen, J.R., Takahashi, M., Kushida, K., Suzuki, M., Suzuki, K., Horiuchi, K., Nagano, A. Anal. Biochem. (2000) [Pubmed]
  30. Desmosine and isodesmosine as cross-links in the hinge-ligament protein of bivalves. 3,3'-Methylenebistyrosine as an artefact. Kikuchi, Y., Tsuchikura, O., Hirama, M., Tamiya, N. Eur. J. Biochem. (1987) [Pubmed]
 
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