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Chemical Compound Review

AC1L3XHJ     (2S)-2-amino-6-[[2-(2-furyl)- 2-oxo...

Synonyms: AR-1J3313, N6-(2-(2-Furanyl-2-oxoethyl))-L-lysine
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Disease relevance of furosine


Psychiatry related information on furosine

  • Protein glycation was evaluated in plasma with a highly specific HPLC-UV technique, using furosine, which is the acid hydrolysis product of epsilon-deoxy-fructosyl-lysine Plasma furosine was almost two times higher in subjects with Alzheimer's disease (p<.005) than in controls, but still 50% lower than in diabetic patients (P<.02) [5].

High impact information on furosine


Biological context of furosine

  • RESULTS: ECs cultured in the presence of GA at furosine concentrations corresponding to levels in diabetic patients showed a significant enhancement of apoptosis [11].
  • The reaction kinetics of two heat damage indices, HMF and furosine, were examined in four tomato products with different dry matter contents (10.2, 25.5, 28.6, and 34.5%) over a temperature-time range of 80-120 degrees C and 0-255 min [12].
  • In the context of identifying intrinsic time temperature integrators (TTIs) for evaluating thermal processing of milk, the possible influence of seasonal variation in milk composition on the applicability of alkaline phosphatase (ALP), hydroxymethylfurfural (HMF), lactulose and furosine for process impact assessment was studied [13].
  • The extent of non-enzymatic glycosylation was measured by furosine content [14].
  • The values of motor nerve conduction velocity and sensory nerve conduction velocity were better correlated with the level of furosine in hair corresponding in the length to 1 year's growth than the levels of FPG and hemoglobin A1c at the time of the determination of nerve conduction velocity [15].

Anatomical context of furosine

  • Quantitation of lysine-bound glucose of normal and diabetic erythrocyte membranes by HPLC analysis of furosine [ epsilon-N(L-furoylmethyl)-L-lysine] [16].
  • In sciatic nerve cytoskeletal preparations from both diabetic and control animals we found high levels of the early glycation product (measured as furosine) after 6 weeks, which had fallen markedly by 8 months [17].
  • METHODS: Murine (t End.1) or human umbilical vein ECs (HUVECs) were incubated with graded GA concentrations (furosine 0.48-96 nmol/ml) at levels that approximated those reported in sera of diabetic patients (76 +/- 0.02 nmol/ml) [11].
  • While the furosine levels in these samples correlated poorly with fasting plasma glucose (FPG) and with hemoglobin A1c (HbA1c) levels at the time of sampling, better correlations were observed between glycation and the year-long average values of FPG, HbA1c, and the conduction velocities in two peripheral nerves [18].
  • Protein-bound product size and in situ formation of furosine in the peritoneal cavity would be the reason for these differences in D/P [4].

Associations of furosine with other chemical compounds


Gene context of furosine

  • CONCLUSIONS: We found that Amadori-configurated GA at furosine concentrations similar to those in diabetic patients favoured EC apoptosis through enhancement of iNOS activity [11].
  • RESULTS: In both proteins, furosine and CML were progressively generated in accordance with the duration of the incubation period [22].
  • Diabetic patients on SHD showed similar levels of glycation indexes as non-diabetic patients, except for the early product furosine that was notably higher [23].
  • IMP and DP were stored at 4, 20, and 37 degrees C for approximately 5 months; periodically samples were analyzed to evaluate heat and oxidative damage by measurement of color changes, total phenolics, rutin, lycopene and furosine concentrations, and antioxidant activity of the lipophilic extract [24].
  • 9 kJ/mol and 19.2 degrees C for HMF, and 93.9 kJ/mol and 28.4 degrees C for furosine [12].

Analytical, diagnostic and therapeutic context of furosine


  1. Glycation of cataractous lens in non-diabetic senile subjects and in diabetic patients. Oimomi, M., Maeda, Y., Hata, F., Kitamura, Y., Matsumoto, S., Baba, S., Iga, T., Yamamoto, M. Exp. Eye Res. (1988) [Pubmed]
  2. An oral load of the early glycation compound lactuloselysine fails to accumulate in the serum of uraemic patients. Schwenger, V., Morath, C., Schönfelder, K., Klein, W., Weigel, K., Deppisch, R., Henle, T., Ritz, E., Zeier, M. Nephrol. Dial. Transplant. (2006) [Pubmed]
  3. Glycosylated proteins of skin, nail and hair: application as an index for long-term control of diabetes mellitus. Sueki, H., Nozaki, S., Fujisawa, R., Aoki, K., Kuroiwa, Y. J. Dermatol. (1989) [Pubmed]
  4. Kinetic analysis of furosine and pentosidine in CAPD patients. Kumano, K., Yokota, S., Sakai, T., Kobayashi, N., Yoshida, A., Yoshihara, T., Shibata, K., Izumi, G., Wang, H. Advances in peritoneal dialysis. Conference on Peritoneal Dialysis. (1997) [Pubmed]
  5. Plasma protein glycation in Alzheimer's disease. Riviere, S., Birlouez-Aragon, I., Vellas, B. Glycoconj. J. (1998) [Pubmed]
  6. Longitudinal determination of skin collagen glycation and glycoxidation rates predicts early death in C57BL/6NNIA mice. Sell, D.R., Kleinman, N.R., Monnier, V.M. FASEB J. (2000) [Pubmed]
  7. Reduced levels of oxidized and glycoxidized proteins in human fibroblasts exposed to repeated mild heat shock during serial passaging in vitro. Verbeke, P., Clark, B.F., Rattan, S.I. Free Radic. Biol. Med. (2001) [Pubmed]
  8. Analysis of epsilon-N-2-furoylmethyl-L-lysine (furosine) in dried milk by capillary electrophoresis with controlled electroosmotic flow using N,N,N',N'-tetramethyl-1,3-butanediamine in the running electrolyte solution. Corradini, D., Cannarsa, G., Corradini, C., Nicoletti, I., Pizzoferrato, L., Vivanti, V. Electrophoresis (1996) [Pubmed]
  9. Is serum fructosamine assay specific for determination of glycated serum protein? Schleicher, E.D., Mayer, R., Wagner, E.M., Gerbitz, K.D. Clin. Chem. (1988) [Pubmed]
  10. The protective effect of aminoguanidine on erectile function in streptozotocin diabetic rats. Usta, M.F., Bivalacqua, T.J., Yang, D.Y., Ramanitharan, A., Sell, D.R., Viswanathan, A., Monnier, V.M., Hellstrom, W.J. J. Urol. (2003) [Pubmed]
  11. Amadori-configurated albumin induces nitric oxide-dependent apoptosis of endothelial cells: a possible mechanism of diabetic vasculopathy. Amore, A., Cirina, P., Conti, G., Cerutti, F., Bagheri, N., Emancipator, S.N., Coppo, R. Nephrol. Dial. Transplant. (2004) [Pubmed]
  12. Hydroxymethylfurfural and furosine reaction kinetics in tomato products. Hidalgo, A., Pompei, C. J. Agric. Food Chem. (2000) [Pubmed]
  13. Influence of seasonal variation on kinetics of time temperature integrators for thermally processed milk. Claeys, W.L., Van Loey, A.M., Hendrickx, M.E. J. Dairy Res. (2003) [Pubmed]
  14. Effect of non-enzymatic glycosylation and heating on browning of human stratum corneum and nail. Sueki, H., Nozaki, S., Numazawa, S., Aoki, K., Kuroiwa, Y., Fujisawa, R. Dermatologica (1991) [Pubmed]
  15. Clinical application of hair protein glycation in the assessment of blood glucose control and diabetic neuropathy. Masuta, S., Sakai, M., Ohara, T., Igaki, N., Nakamichi, T., Maeda, Y., Hata, F., Oimomi, M., Baba, S. The Kobe journal of medical sciences. (1989) [Pubmed]
  16. Quantitation of lysine-bound glucose of normal and diabetic erythrocyte membranes by HPLC analysis of furosine [ epsilon-N(L-furoylmethyl)-L-lysine]. Schleicher, E., Scheller, L., Wieland, O.H. Biochem. Biophys. Res. Commun. (1981) [Pubmed]
  17. Nonenzymatic glycation of peripheral and central nervous system proteins in experimental diabetes mellitus. Ryle, C., Leow, C.K., Donaghy, M. Muscle Nerve (1997) [Pubmed]
  18. Hair protein glycation as a long-term index of blood glucose in diabetics. Oimomi, M., Igaki, N., Masuda, S., Hata, F., Maeda, Y., Matsumoto, S., Baba, S. Diabetes Res. Clin. Pract. (1988) [Pubmed]
  19. Generation of furosine and color in infant/enteral formula-resembling systems. Rufián-Henares, J.A., García-Villanova, B., Guerra-Hernández, E. J. Agric. Food Chem. (2004) [Pubmed]
  20. Ratio of maltose to maltulose and furosine as quality parameters for infant formula. Morales, V., Olano, A., Corzo, N. J. Agric. Food Chem. (2004) [Pubmed]
  21. Furosine as indicator of maillard reaction in jams and fruit-based infant foods. Rada-Mendoza, M., Olano, A., Villamiel, M. J. Agric. Food Chem. (2002) [Pubmed]
  22. Suppression of N(epsilon)-(carboxymethyl)lysine generation by the antioxidant N-acetylcysteine. Nakayama, M., Izumi, G., Nemoto, Y., Shibata, K., Hasegawa, T., Numata, M., Wang, K., Kawaguchi, Y., Hosoya, T. Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis. (1999) [Pubmed]
  23. Daily haemodialysis improves indices of protein glycation. Floridi, A., Antolini, F., Galli, F., Fagugli, R.M., Floridi, E., Buoncristiani, U. Nephrol. Dial. Transplant. (2002) [Pubmed]
  24. Stability of dried and intermediate moisture tomato pulp during storage. Giovanelli, G., Paradiso, A. J. Agric. Food Chem. (2002) [Pubmed]
  25. Temperature effect on lactose crystallization, maillard reactions, and lipid oxidation in whole milk powder. Thomsen, M.K., Lauridsen, L., Skibsted, L.H., Risbo, J. J. Agric. Food Chem. (2005) [Pubmed]
  26. Determination of furosine in biomedical samples employing an improved hydrolysis and high-performance liquid chromatographic technique. Cefalu, W.T., Bell-Farrow, A., Wang, Z.Q., Ralapati, S. Carbohydr. Res. (1991) [Pubmed]
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