D9439

Sigma-Aldrich

Desmosine chloride

from bovine, 99.5%±0.2%

Empirical Formula (Hill Notation):
C24H40ClN5O8
CAS Number:
Molecular Weight:
562.06
MDL number:
PubChem Substance ID:
NACRES:
NA.56

Quality Level

biological source

bovine

assay

99.5%±0.2%

form

lyophilized powder

purified by

chromatography (and purified by solvent extraction)

storage temp.

2-8°C

SMILES string

[Cl-].NC(CCCC[n+]1cc(CCC(N)C(O)=O)c(CCCC(N)C(O)=O)c(CCC(N)C(O)=O)c1)C(O)=O

InChI

1S/C24H39N5O8.ClH/c25-17(21(30)31)5-1-2-11-29-12-14(7-9-19(27)23(34)35)16(4-3-6-18(26)22(32)33)15(13-29)8-10-20(28)24(36)37;/h12-13,17-20H,1-11,25-28H2,(H3-,30,31,32,33,34,35,36,37);1H

InChI key

FUPMLZCXPJSGPV-UHFFFAOYSA-N

General description

Each vial contains 1 μmole of purified desmosine.

Application

Desmosine chloride is often used in assays for free or urinary desmosine as markers for disease states characterized by elastin degradation (e.g., emphysema). Elastin degradation has shown strong correlation with vascular calcification, and pretreatment with aluminum ions can inhibit the binding of matrix metalloproteinase (MMP) to elastin.
Assays for free or urinary desmosine are often used as markers for disease states characterized by elastin degradation (e.g., emphysema). Conversely, excessive levels of incorporated desmosine are indicators of fibrotic conditions (e.g., cirrhosis).

Biochem/physiol Actions

Desmosine is a polyfunctional amino acid that forms cross-links in mature elastin.

Caution

Extremely hygroscopic

Analysis Note

Calibrated by UV and amino acid analysis.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Franca Cocci et al.
The international journal of biochemistry & cell biology, 34(6), 594-604 (2002-04-12)
An enhanced proteolysis of lung interstitium is key event in the pathogenesis of emphysema, a major constituent of chronic obstructive pulmonary disease. To assess whether urinary desmosine and/or hydroxyproline may be used as a marker of lung destruction we studied...
M Bailey et al.
The American journal of pathology, 159(6), 1981-1986 (2001-12-26)
Calcification of elastin occurs in many pathological cardiovascular diseases including atherosclerosis. We have previously shown that purified elastin when subdermally implanted in rats undergoes severe calcification and aluminum chloride (AlCl(3)) pretreatment of elastin inhibits calcification. In the present study we...
Dina M Basalyga et al.
Circulation, 110(22), 3480-3487 (2004-11-17)
Elastin calcification is a widespread feature of vascular pathology, and circumstantial evidence exists for a correlation between elastin degradation and calcification. We hypothesized that matrix metalloproteinase (MMP)-mediated vascular remodeling plays a significant role in elastin calcification. In the present studies...

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