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Chemical Compound Review

Pyrraline     (2S)-2-amino-6-[2- (hydroxymethyl)-5...

Synonyms: CHEBI:59973, AC1Q5QLY, CTK8D4821, AR-1H0664, AC1L3U7Y, ...
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Disease relevance of Pyrraline


High impact information on Pyrraline

  • To assess the possible link between AGE accumulation and the development of diabetic nephropathy (DN), we have examined the immunohistochemical localization of various AGE structures postulated to date, i.e., pentosidine, Nepsilon-(carboxymethyl)lysine (CML), and pyrraline, in diabetic and control kidneys [5].
  • By contrast, pyrraline was not found within diabetic glomeruli but was detected in the interstitial connective tissue of both normal and diabetic kidneys [5].
  • The preferential localization of pyrraline immunoreactivity in the extracellular matrix strengthens the notion that the advanced glycosylation reaction may contribute to decreased turnover and thickening of the extracellular matrix in diabetes and aging [1].
  • Immunohistochemical detection of advanced glycosylation end products in diabetic tissues using monoclonal antibody to pyrraline [1].
  • Plasma pyrraline levels increased fourfold (P less than 0.001) in Sprague-Dawley rats upon induction of diabetes with streptozotocin and were twofold increased in randomly selected plasmas from diabetic humans [1].

Chemical compound and disease context of Pyrraline


Biological context of Pyrraline


Anatomical context of Pyrraline


Associations of Pyrraline with other chemical compounds

  • Elevated levels of advanced glycation end-product-derived fluorescence and pyrraline in renal cortex and aorta of diabetic rats were suppressed by the administration of tenilsetam for 16 weeks [12].
  • Furthermore, it is likely that the accumulation of pyrraline and imidazolone supports a nonoxidative mechanism in SOD1-related motor neuron degeneration [13].
  • Inhibition of in vitro pyrraline formation by L-arginine and polyamines [14].
  • Heparin also induced a tendency of increased dialysate pyrraline levels and a significant increase in AGE-derived fluorescence intensity in the dialysate [15].
  • Two compounds were identified from the pH 5 glucose system and were identified as epsilon-[2-formyl-5-(hydroxymethyl)pyrrole-1-yl]-L-norleucine (pyrraline) and the new compound, 1-(5-carboxy-5-aminopentyl)-2-formyl-3-(1,2,3-trihydroxypropyl)pyrrole [16].

Gene context of Pyrraline


Analytical, diagnostic and therapeutic context of Pyrraline

  • Using reversed-phase high-performance liquid chromatography, we measured urinary pyrraline in 45 insulin-treated diabetic patients with preserved renal function and in 30 age- and sex-matched healthy subjects [20].
  • Antibodies were raised to caproyl-pyrraline linked to keyhole-limpet haemocyanin and were used to develop an e.l.i.s.a. and Western blotting system for the specific detection of pyrraline in samples in vivo and in vitro [21].
  • We collected 24 h urine samples for these 5 days, which were analysed for free pyrraline by reverse-phase HPLC with UV detection at 297 nm [22].
  • Pyrraline levels were determined by ELISA [15].


  1. Immunohistochemical detection of advanced glycosylation end products in diabetic tissues using monoclonal antibody to pyrraline. Miyata, S., Monnier, V. J. Clin. Invest. (1992) [Pubmed]
  2. First evidence for accumulation of protein-bound and protein-free pyrraline in human uremic plasma by mass spectrometry. Odani, H., Shinzato, T., Matsumoto, Y., Takai, I., Nakai, S., Miwa, M., Iwayama, N., Amano, I., Maeda, K. Biochem. Biophys. Res. Commun. (1996) [Pubmed]
  3. Structure of advanced Maillard reaction products and their pathological role. Monnier, V.M., Nagaraj, R.H., Portero-Otin, M., Glomb, M., Elgawish, A.H., Sell, D.R., Friedlander, M.A. Nephrol. Dial. Transplant. (1996) [Pubmed]
  4. Glycoxidation and oxidative stress in Parkinson disease and diffuse Lewy body disease. Castellani, R., Smith, M.A., Richey, P.L., Perry, G. Brain Res. (1996) [Pubmed]
  5. Immunohistochemical colocalization of glycoxidation products and lipid peroxidation products in diabetic renal glomerular lesions. Implication for glycoxidative stress in the pathogenesis of diabetic nephropathy. Horie, K., Miyata, T., Maeda, K., Miyata, S., Sugiyama, S., Sakai, H., van Ypersole de Strihou, C., Monnier, V.M., Witztum, J.L., Kurokawa, K. J. Clin. Invest. (1997) [Pubmed]
  6. Advanced glycation end product deposits in climatic droplet keratopathy. Kaji, Y., Nagai, R., Amano, S., Takazawa, Y., Fukayama, M., Oshika, T. The British journal of ophthalmology (2007) [Pubmed]
  7. Aging of proteins: immunological detection of a glucose-derived pyrrole formed during maillard reaction in vivo. Hayase, F., Nagaraj, R.H., Miyata, S., Njoroge, F.G., Monnier, V.M. J. Biol. Chem. (1989) [Pubmed]
  8. High levels of urinary pentosidine, an advanced glycation end product, in children with acute exacerbation of atopic dermatitis: relationship with oxidative stress. Tsukahara, H., Shibata, R., Ohta, N., Sato, S., Hiraoka, M., Ito, S., Noiri, E., Mayumi, M. Metab. Clin. Exp. (2003) [Pubmed]
  9. Advanced Maillard reaction end products are associated with Alzheimer disease pathology. Smith, M.A., Taneda, S., Richey, P.L., Miyata, S., Yan, S.D., Stern, D., Sayre, L.M., Monnier, V.M., Perry, G. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  10. Accumulation of pyrraline-modified albumin in phagocytes due to reduced degradation by lysosomal enzymes. Miyata, S., Liu, B.F., Shoda, H., Ohara, T., Yamada, H., Suzuki, K., Kasuga, M. J. Biol. Chem. (1997) [Pubmed]
  11. Glycoxidation and lipid peroxidation of low-density lipoprotein can synergistically enhance atherogenesis. Sakata, N., Uesugi, N., Takebayashi, S., Nagai, R., Jono, T., Horiuchi, S., Takeya, M., Itabe, H., Takano, T., Myint, T., Taniguchi, N. Cardiovasc. Res. (2001) [Pubmed]
  12. Inhibitory effects of tenilsetam on the Maillard reaction. Shoda, H., Miyata, S., Liu, B.F., Yamada, H., Ohara, T., Suzuki, K., Oimomi, M., Kasuga, M. Endocrinology (1997) [Pubmed]
  13. Nonoxidative protein glycation is implicated in familial amyotrophic lateral sclerosis with superoxide dismutase-1 mutation. Shibata, N., Nagai, R., Miyata, S., Jono, T., Horiuchi, S., Hirano, A., Kato, S., Sasaki, S., Asayama, K., Kobayashi, M. Acta Neuropathol. (2000) [Pubmed]
  14. Inhibition of in vitro pyrraline formation by L-arginine and polyamines. Méndez, J.D., Leal, L.I. Biomed. Pharmacother. (2004) [Pubmed]
  15. Effect of intraperitoneal administration of heparin on advanced glycation end-products in CAPD. Mizuiri, S., Miyata, S., Sakai, K., Kobayashi, M., Miyagi, M., Nakanishi, T., Liu, B.F., Kojima, H., Hasegawa, A. Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis. (1999) [Pubmed]
  16. Identification of new heterocyclic nitrogen compounds from glucose-lysine and xylose-lysine maillard model systems. Bailey, R.G., Ames, J.M., Mann, J. J. Agric. Food Chem. (2000) [Pubmed]
  17. Glycoxidative modification of AA amyloid deposits in renal tissue. Uesugi, N., Sakata, N., Nagai, R., Jono, T., Horiuchi, S., Takebayashi, S. Nephrol. Dial. Transplant. (2000) [Pubmed]
  18. Dissociation between urinary pyrraline and pentosidine concentrations in diabetic patients with advanced nephropathy. Aso, Y., Takanashi, K., Sekine, K., Yoshida, N., Takebayashi, K., Yoshihara, K., Inukai, T. J. Lab. Clin. Med. (2004) [Pubmed]
  19. Effect of Maillard reaction products on protein digestion. Oste, R. Prog. Clin. Biol. Res. (1989) [Pubmed]
  20. Glycaemic control and in vivo non-oxidative Maillard reaction: urinary excretion of pyrraline in diabetes patients. Portero-Otín, M., Pamplona, R., Bellmunt, M.J., Bergua, M., Prat, J. Eur. J. Clin. Invest. (1997) [Pubmed]
  21. Evidence against the formation of 2-amino-6-(2-formyl-5-hydroxymethyl-pyrrol-1-yl)-hexanoic acid ('pyrraline') as an early-stage product or advanced glycation end product in non-enzymic protein glycation. Smith, P.R., Somani, H.H., Thornalley, P.J., Benn, J., Sonksen, P.H. Clin. Sci. (1993) [Pubmed]
  22. Glycation in food and metabolic transit of dietary AGEs (advanced glycation end-products): studies on the urinary excretion of pyrraline. Foerster, A., Henle, T. Biochem. Soc. Trans. (2003) [Pubmed]
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