Pyridinoline

Pyridinoline
Identifiers
CAS Number	63800-01-1;
ChemSpider	94798;
PubChem CID	105068;
CompTox Dashboard (EPA)	DTXSID00980373 ;
Properties
Chemical formula	C18H28N4O8
Molar mass	428.43692 g mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Pyridinoline, also known as Hydroxylysylpyridinoline, is a fluorescent cross-linking compound of collagen fibers. Crosslinks in collagen and elastin are derived from lysyl and hydroxylysyl residues,[1] a process catalyzed by lysyl oxidase. Fujimoto and colleagues first described the isolation and characterization of a fluorescent material in bovine Achilles tendon collagen and termed it pyridinoline.[2] It is reported to be present in collagen of bone and cartilage, but is absent in collagen of skin. It is not present in newly synthesized collagen and is formed from aldimine cross-links during maturation of collagen fibers.[3]

Pyridinoline and deoxypyridinoline were found to be released into the blood during bone degradation and rapidly excreted in the urine. In a preliminary study, both these compounds were proposed as a marker for metastatic bone tumor in patients with prostate cancer.[4]

References

Gallop PM, Blumenfeld OO, Seifter S (1972). "Structure and metabolism of connective tissue proteins". Annual Review of Biochemistry. 41 (1): 617–72. doi:10.1146/annurev.bi.41.070172.003153. PMID 4343456.
Fujimoto D, Akiba K, Nakamura N (June 1977). "Isolation and characterization of a fluorescent material in bovine achilles tendon collagen". Biochemical and Biophysical Research Communications. 76 (4): 1124–9. doi:10.1016/0006-291X(77)90972-X. PMID 901463.]
Uchiyama A, Inoue T, Fujimoto D (December 1981). "Synthesis of pyridinoline during in vitro aging of bone collagen". Journal of Biochemistry. 90 (6): 1795–8. doi:10.1093/oxfordjournals.jbchem.a133657. PMID 7334012.
Samma S, Kagebayashi Y, Yasukawa M, et al. (February 1997). "Sequential changes of urinary pyridinoline and deoxypyridinoline as markers of metastatic bone tumor in patients with prostate cancer: a preliminary study". Japanese Journal of Clinical Oncology. 27 (1): 26–30. doi:10.1093/jjco/27.1.26. PMID 9070337.

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[1] Gallop PM, Blumenfeld OO, Seifter S (1972). "Structure and metabolism of connective tissue proteins". Annual Review of Biochemistry. 41 (1): 617–72. doi:10.1146/annurev.bi.41.070172.003153. PMID 4343456.

[2] Fujimoto D, Akiba K, Nakamura N (June 1977). "Isolation and characterization of a fluorescent material in bovine achilles tendon collagen". Biochemical and Biophysical Research Communications. 76 (4): 1124–9. doi:10.1016/0006-291X(77)90972-X. PMID 901463.]

[3] Uchiyama A, Inoue T, Fujimoto D (December 1981). "Synthesis of pyridinoline during in vitro aging of bone collagen". Journal of Biochemistry. 90 (6): 1795–8. doi:10.1093/oxfordjournals.jbchem.a133657. PMID 7334012.

[4] Samma S, Kagebayashi Y, Yasukawa M, et al. (February 1997). "Sequential changes of urinary pyridinoline and deoxypyridinoline as markers of metastatic bone tumor in patients with prostate cancer: a preliminary study". Japanese Journal of Clinical Oncology. 27 (1): 26–30. doi:10.1093/jjco/27.1.26. PMID 9070337.