Desmosine
Desmosine is formed by condensation of four moleclies of lysine into a pyridinium ring. Elastin moleclies aggregate in the extracellliar space where they are crosslinked by stable desmosine bridges. The resliting polymer is structurally organized as branched fibers and lamellae, which, in skin, are wider (a few microns) in the deep dermis and become progressively thinner (fraction of a micron) towards the papillary dermis. Several general and local factors seem to regliate elastin gene expression, deposition and degradation. (PMID: 9297692 ). Desmosines are crosslinking amino acids unique to mature elastin in humans. Owing to this unicity, they have been discussed as potentially indicators of connective tissue disorders whose clinical manifestations are mostly the reslit of elastin degradation. (PMID: 17390614 ). Emphysema (Plimonary emphysema is a devastating disease for which there is no effective treatment) is associated with degradation of elastic fibers (PMID: 14704646 ). It has been shown that the urinary concentration of elastin specific crosslinks, desmosine correlates well with liver fibrosis score in biopsy specimens from patients with liver disease secondary to hepatitis C virus and alcohol. (PMID: 10996125 ).
Structure for HMDB00572 (Desmosine)
C24H40N5O8
526.6031
526.287688281
3,5-bis[(3S)-3-amino-3-carboxypropyl]-4-[(4S)-4-amino-4-carboxybutyl]-1-(5-amino-5-carboxypentyl)pyridin-1-ium
3,5-bis[(3S)-3-amino-3-carboxypropyl]-4-[(4S)-4-amino-4-carboxybutyl]-1-(5-amino-5-carboxypentyl)pyridin-1-ium
11003-57-9
VEVRNHHLCPGNDU-NIVVRJPPSA-O
This compound belongs to the class of chemical entities known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
Chemical entities
Organic compounds
Organic acids and derivatives
Carboxylic acids and derivatives
Tetracarboxylic acids and derivatives
Aromatic heteromonocyclic compounds
Not Available
Detected and Quantified
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Solid
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
Not Available
None
None
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FDB000516
Not Available
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Desmosine
HMDB00572
HMDB00572
5554
53477704
Not Available
37628
- Luisetti M, Sturani C, Sella D, Madonini E, Galavotti V, Bruno G, Peona V, Kucich U, Dagnino G, Rosenbloom J, Starcher B, Grassi C: MR889, a neutrophil elastase inhibitor, in patients with chronic obstructive pulmonary disease: a double-blind, randomized, placebo-controlled clinical trial. Eur Respir J. 1996 Jul;9(7):1482-6. [PubMed:8836663 ]
- Ono S, Yamauchi M: Elastin cross-linking in the skin from patients with amyotrophic lateral sclerosis. J Neurol Neurosurg Psychiatry. 1994 Jan;57(1):94-6. [PubMed:8301312 ]
- Uitto J, Santa Cruz DJ, Starcher BC, Whyte MP, Murphy WA: Biochemical and ultrastructural demonstration of elastin accumulation in the skin lesions of the Buschke-Ollendorff syndrome. J Invest Dermatol. 1981 Apr;76(4):284-7. [PubMed:7205030 ]
- Tenholder MF, Rajagopal KR, Phillips YY, Dillard TA, Bennett LL, Mundie TG, Tellis CJ: Urinary desmosine excretion as a marker of lung injury in the adult respiratory distress syndrome. Chest. 1991 Nov;100(5):1385-90. [PubMed:1935298 ]
- Fill JA, Brandt JT, Wiedemann HP, Rinehart BL, Lindemann CF, Komara JJ, Bowsher RR, Spence MC, Zeiher BG: Urinary desmosine as a biomarker in acute lung injury. Biomarkers. 2006 Jan-Feb;11(1):85-96. [PubMed:16484139 ]
- Viglio S, Iadarola P, Lupi A, Trisolini R, Tinelli C, Balbi B, Grassi V, Worlitzsch D, Doring G, Meloni F, Meyer KC, Dowson L, Hill SL, Stockley RA, Luisetti M: MEKC of desmosine and isodesmosine in urine of chronic destructive lung disease patients. Eur Respir J. 2000 Jun;15(6):1039-45. [PubMed:10885422 ]
- Ma S, Lieberman S, Turino GM, Lin YY: The detection and quantitation of free desmosine and isodesmosine in human urine and their peptide-bound forms in sputum. Proc Natl Acad Sci U S A. 2003 Oct 28;100(22):12941-3. Epub 2003 Oct 16. [PubMed:14563926 ]
- Oikarinen AI, Palatsi R, Adomian GE, Oikarinen H, Clark JG, Uitto J: Anetoderma: biochemical and ultrastructural demonstration of an elastin defect in the skin of three patients. J Am Acad Dermatol. 1984 Jul;11(1):64-72. [PubMed:6736354 ]
- Wondrak GT, Roberts MJ, Jacobson MK, Jacobson EL: 3-hydroxypyridine chromophores are endogenous sensitizers of photooxidative stress in human skin cells. J Biol Chem. 2004 Jul 16;279(29):30009-20. Epub 2004 May 7. [PubMed:15133022 ]
- Pasquali-Ronchetti I, Baccarani-Contri M: Elastic fiber during development and aging. Microsc Res Tech. 1997 Aug 15;38(4):428-35. [PubMed:9297692 ]
- Viglio S, Annovazzi L, Luisetti M, Stolk J, Casado B, Iadarola P: Progress in the methodological strategies for the detection in real samples of desmosine and isodesmosine, two biological markers of elastin degradation. J Sep Sci. 2007 Feb;30(2):202-13. [PubMed:17390614 ]
- Cantor JO, Shteyngart B: How a test for elastic fiber breakdown products in sputum could speed development of a treatment for pulmonary emphysema. Med Sci Monit. 2004 Jan;10(1):RA1-4. [PubMed:14704646 ]
- Stone PJ: Potential use of collagen and elastin degradation markers for monitoring liver fibrosis in schistosomiasis. Acta Trop. 2000 Oct 23;77(1):97-9. [PubMed:10996125 ]