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Chemical Compound Review

4-hydroxyproline     4-hydroxypyrrolidine-2- carboxylic acid

Synonyms: SureCN22792, AG-F-66688, CHEMBL1213475, ACMC-209gms, ACMC-209ktb, ...
 
 
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Disease relevance of oxyproline

  • Thus, the cHyp polymer is a potent, long-acting antifibrotic agent which may be useful in treating lung fibrosis [1].
  • In summary, the prevention of an increase in HOProl excretion accompanied by the fact that final BMD and BMC in OLP-treated animals were comparable to sham control rats may reflect that OLP administration could inhibit bone resorption in both T4-treated or -untreated rats [2].
  • [Oxyproline metabolism in periodontosis] [3].
 

High impact information on oxyproline

  • These results suggest that there is a competing, deactivation reaction; namely, the thiol ester and oxyproline intermediates are hydrolyzed to regenerate the active site glutamic acid [4].
  • The gamma-glutamyl cycle is expected to generate pyroglutamate (synonymous with oxyproline) within the endothelial cells [5].
  • In contrast, D-pen caused a progressive accumulation of hydroxyproline (Hyp) in the aortic wall during and after treatment, probably mediated by an increased number of matrix synthesizing cells, as judged by augmentation of the DNA content in the presence of unaltered Hyp/DNA and RNA/DNA ratios [6].
  • When explants of this lung tissue were cultured, proliferation of cuboidal epithelial cells was reduced, whereas fibroblast growth and hydroxyproline (HYP) levels were significantly higher than in controls [7].
  • Calcitonin therapy caused a 31% reduction in ALP and a 50% reduction in HP, as well as a significant increase in serum levels of 24,25 (OH) 2D3; the levels of 25OHD3, 1,25 (OH) 2D3, and PTH remained unchanged after treatment [8].
 

Chemical compound and disease context of oxyproline

  • RESULTS: Leflunomide (1, 3, and 9 mg/kg) significantly decreased indices of liver and spleen, the serum transaminase (AST, ALT) activities, HA and PC III levels, and Hyp contents in liver tissue in rats of hepatic fibrosis [9].
 

Biological context of oxyproline

 

Anatomical context of oxyproline

 

Associations of oxyproline with other chemical compounds

  • The liver hydroxyproline (HYP), liver function and hyaluronic acid (HA) were examined by biochemistry and radioimmunoassay (RIA) respectively [12].
  • Distinct, dependent on the time of day disturbances in circadian fluctuations of PICP, ICTP, HYP and Ca showing generally negative correlation with changes in endogenous MEL concentrations and positive with IGF-I and corticosterone (B) levels were found [13].
  • Moreover, ICTP, HYP and Ca concentrations correlated positively with daily fluctuations of IGF-I and triiodothyronine [14].
  • We also observed an increase in reactive oxygen species generation and activation of caspase-9 with adriamycin in a hydroxyproline-dependent manner [15].
 

Gene context of oxyproline

  • Neither serum ALP nor urinary Hyp correlated with the percent changes of spine or femoral neck BMD measurements taken the year or 2 years after the sera and urine sampling [16].
 

Analytical, diagnostic and therapeutic context of oxyproline

  • Cartilage degradation was assessed by quantitating sulfated glycosaminoglycan (S-GAG) to hydroxyproline (Hyp) and appearance of keratan sulfate (KS) in synovial lavage by and ELISA [17].

References

  1. Polymer of proline analogue with sustained antifibrotic activity in lung fibrosis. Greco, M.J., Kemnitzer, J.E., Fox, J.D., Choe, J.K., Kohn, J., Riley, D.J., Poiani, G.J. Am. J. Respir. Crit. Care Med. (1997) [Pubmed]
  2. The effect of olpadronate in ovariectomized thyroxine-treated rats. Zeni, S., Gomez-Acotto, C., Mautalen, C. Bone (1997) [Pubmed]
  3. [Oxyproline metabolism in periodontosis]. Kulikova, V.S., Nikitina, T.V. Stomatologiia. (1975) [Pubmed]
  4. Mechanism-based fragmentation of coenzyme A transferase. Comparison of alpha 2-macroglobulin and coenzyme A transferase thiol ester reactions. Howard, J.B., Zieske, L., Clarkson, J., Rathe, L. J. Biol. Chem. (1986) [Pubmed]
  5. Structure of the blood-brain barrier and its role in the transport of amino acids. Hawkins, R.A., O'Kane, R.L., Simpson, I.A., Viña, J.R. J. Nutr. (2006) [Pubmed]
  6. D-penicillamine-induced angiopathy in rats. Changes in aortic collagen, glycosaminoglycans, DNA and RNA in rats treated with D-penicillamine. Junker, P., Helin, G., Jensen, B.A., Oxlund, H., Lorenzen, I. Atherosclerosis (1982) [Pubmed]
  7. Fibroblast inhibition does not promote normal lung repair after hyperoxia. Bowden, D.H., Young, L., Adamson, I.Y. Exp. Lung Res. (1994) [Pubmed]
  8. Vitamin D status in Paget's bone disease. Effects of calcitonin therapy. Nunziata, V., Giannattasio, R., di Giovanni, G., Lettera, A.M., Nunziata, C.A. Clin. Orthop. Relat. Res. (1993) [Pubmed]
  9. Inhibitory effect of leflunomide on hepatic fibrosis induced by CCl4 in rats. Yao, H.W., Li, J., Chen, J.Q., Xu, S.Y. Acta Pharmacol. Sin. (2004) [Pubmed]
  10. Effect of thyroxine therapy on bone metabolism in substituted hypothyroid patients with normal or suppressed levels of TSH. Gam, A.N., Jensen, G.F., Hasselstrøm, K., Olsen, M., Nielsen, K.S. J. Endocrinol. Invest. (1991) [Pubmed]
  11. Hepatic damage in biliary-obstructed rats is ameliorated by leflunomide treatment. Karaman, A., Iraz, M., Kirimlioglu, H., Karadag, N., Tas, E., Fadillioglu, E. Pediatr. Surg. Int. (2006) [Pubmed]
  12. JinSanE Decoction, A Chinese Herbal Medicine, Inhibits Expression of TGF-beta1/Smads in Experimental Hepatic Fibrosis in Rats. Song, S.L., Gong, Z.J., Huang, Y.Q., Zhang, Q.R., Huang, T.X. Am. J. Chin. Med. (2006) [Pubmed]
  13. The relationship between bone metabolism, melatonin and other hormones in sham-operated and pinealectomized rats. Ostrowska, Z., Kos-Kudla, B., Nowak, M., Swietochowska, E., Marek, B., Gorski, J., Kajdaniuk, D., Wolkowska, K. Endocrine regulations. (2003) [Pubmed]
  14. Influence of lighting conditions on daily rhythm of bone metabolism in rats and possible involvement of melatonin and other hormones in this process. Ostrowska, Z., Kos-Kudla, B., Marek, B., Kajdaniuk, D. Endocrine regulations. (2003) [Pubmed]
  15. A novel function for hydroxyproline oxidase in apoptosis through generation of reactive oxygen species. Cooper, S.K., Pandhare, J., Donald, S.P., Phang, J.M. J. Biol. Chem. (2008) [Pubmed]
  16. Urinary collagen crosslinks reflect further bone loss of femoral neck in osteoporotic patients undergoing vitamin D therapy. Ohishi, T., Takahashi, M., Kushida, K., Yamazaki, K., Hoshino, H., Kitazawa, A., Inoue, T. Endocr. Res. (1998) [Pubmed]
  17. Elevation of synovial plasminogen activator activity after injection of interleukin-1 alpha into rabbit knee joint. Ganu, V.S., Goldberg, R.L., Blancuzzi, V.J., Wilson, D.E., Doughty, J., Melton, R., O'Byrne, E. Agents Actions (1991) [Pubmed]
 
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