3-Deoxyglucosone (BioDeep_00000173893)

 

Secondary id: BioDeep_00000789541

human metabolite blood metabolite


代谢物信息卡片


4,5,6-trihydroxy-2-oxohexanal

化学式: C6H10O5 (162.052821)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 11.11%

分子结构信息

SMILES: C(C(=O)C=O)[C@@H]([C@@H](CO)O)O
InChI: InChI=1S/C6H10O5/c7-2-4(9)1-5(10)6(11)3-8/h2,5-6,8,10-11H,1,3H2

描述信息

同义名列表

2 个代谢物同义名

4,5,6-trihydroxy-2-oxohexanal; 3-Deoxyglucosone



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Catrin Herpich, Bastian Kochlik, Daniela Weber, Christiane Ott, Tilman Grune, Kristina Norman, Jana Raupbach. Fasting Concentrations and Postprandial Response of 1,2-Dicarbonyl Compounds 3-Deoxyglucosone, Glyoxal, and Methylglyoxal Are Not Increased in Healthy Older Adults. The journals of gerontology. Series A, Biological sciences and medical sciences. 2022 05; 77(5):934-940. doi: 10.1093/gerona/glab331. [PMID: 34726231]
  • Kim Maasen, Simone J P M Eussen, Jean L J M Scheijen, Carla J H van der Kallen, Pieter C Dagnelie, Antoon Opperhuizen, Coen D A Stehouwer, Marleen M J van Greevenbroek, Casper G Schalkwijk. Higher habitual intake of dietary dicarbonyls is associated with higher corresponding plasma dicarbonyl concentrations and skin autofluorescence: the Maastricht Study. The American journal of clinical nutrition. 2022 01; 115(1):34-44. doi: 10.1093/ajcn/nqab329. [PMID: 34625788]
  • M Piazza, N M J Hanssen, F Persson, J L Scheijen, M P H van de Waarenburg, M M J van Greevenbroek, P Rossing, P Hovind, C D A Stehouwer, H-H Parving, C G Schalkwijk. Irbesartan treatment does not influence plasma levels of the dicarbonyls methylglyoxal, glyoxal and 3-deoxyglucosone in participants with type 2 diabetes and microalbuminuria: An IRMA2 sub-study. Diabetic medicine : a journal of the British Diabetic Association. 2021 09; 38(9):e14405. doi: 10.1111/dme.14405. [PMID: 32961617]
  • Shingo Yoshioka, Hiroko Odani, Tadaaki Furuhashi, Tsutomu Tanaka, Toyoaki Ogawa. Increase in the peripheral blood methylglyoxal levels in 10\% of hospitalized chronic schizophrenia patients. Nagoya journal of medical science. 2021 Feb; 83(1):51-61. doi: 10.18999/nagjms.83.1.51. [PMID: 33727737]
  • Jin Cai, Liang Zhou, Xiudao Song, Meiqi Yin, Guoqiang Liang, Heng Xu, Lurong Zhang, Guorong Jiang, Fei Huang. Alteration of Intestinal Microbiota in 3-Deoxyglucosone-Induced Prediabetic Rats. BioMed research international. 2020; 2020(?):8406846. doi: 10.1155/2020/8406846. [PMID: 32908918]
  • Xin-Jie Wang, Hong-Xia Zhang, Heng Li, Ai-Hua Zhu, Wen-Yun Gao. Measurement of α-dicarbonyl compounds in human saliva by pre-column derivatization HPLC. Clinical chemistry and laboratory medicine. 2019 Nov; 57(12):1915-1922. doi: 10.1515/cclm-2019-0350. [PMID: 31377732]
  • Xiudao Song, Guoqiang Liang, Min Shi, Liang Zhou, Fei Wang, Lurong Zhang, Fei Huang, Guorong Jiang. Acute exposure to 3‑deoxyglucosone at high glucose levels impairs insulin secretion from β‑cells by downregulating the sweet taste receptor signaling pathway. Molecular medicine reports. 2019 Jun; 19(6):5015-5022. doi: 10.3892/mmr.2019.10163. [PMID: 31059088]
  • Xin-Jie Wang, Sheng-Bo Ma, Zhuo-Feng Liu, Heng Li, Wen-Yun Gao. Elevated levels of α-dicarbonyl compounds in the plasma of type II diabetics and their relevance with diabetic nephropathy. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 Feb; 1106-1107(?):19-25. doi: 10.1016/j.jchromb.2018.12.027. [PMID: 30639946]
  • Remy J H Martens, Natascha J H Broers, Bernard Canaud, Maarten H L Christiaans, Tom Cornelis, Adelheid Gauly, Marc M H Hermans, Constantijn J A M Konings, Frank M van der Sande, Jean L J M Scheijen, Frank Stifft, Joris J J M Wirtz, Jeroen P Kooman, Casper G Schalkwijk. Relations of advanced glycation endproducts and dicarbonyls with endothelial dysfunction and low-grade inflammation in individuals with end-stage renal disease in the transition to renal replacement therapy: A cross-sectional observational study. PloS one. 2019; 14(8):e0221058. doi: 10.1371/journal.pone.0221058. [PMID: 31408493]
  • L Zhou, X D Song, H Xu, G Q Liang, F Wang, L R Zhang, F Huang, J Cai, G R Jiang. Exogenous 3-Deoxyglucosone-Induced Carbonyl and Oxidative Stress Causes β-Cells Dysfunction by Impairing Gut Permeability in Rats. Biochemistry. Biokhimiia. 2018 Nov; 83(11):1358-1368. doi: 10.1134/s0006297918110068. [PMID: 30482147]
  • Mahmoud H El-Maghrabey, Taro Nakatani, Naoya Kishikawa, Naotaka Kuroda. Aromatic aldehydes as selective fluorogenic derivatizing agents for α-dicarbonyl compounds. Application to HPLC analysis of some advanced glycation end products and oxidative stress biomarkers in human serum. Journal of pharmaceutical and biomedical analysis. 2018 Sep; 158(?):38-46. doi: 10.1016/j.jpba.2018.05.012. [PMID: 29860177]
  • H Malinska, V Škop, J Trnovska, I Markova, P Svoboda, L Kazdova, M Haluzik. Metformin attenuates myocardium dicarbonyl stress induced by chronic hypertriglyceridemia. Physiological research. 2018 05; 67(2):181-189. doi: 10.33549/physiolres.933606. [PMID: 29137475]
  • Juraj Koska, Aramesh Saremi, Scott Howell, Gideon Bahn, Barbora De Courten, Henry Ginsberg, Paul J Beisswenger, Peter D Reaven. Advanced Glycation End Products, Oxidation Products, and Incident Cardiovascular Events in Patients With Type 2 Diabetes. Diabetes care. 2018 03; 41(3):570-576. doi: 10.2337/dc17-1740. [PMID: 29208654]
  • Lurong Zhang, Liang Zhou, Xiudao Song, Guoqiang Liang, Zhongrui Xu, Fei Wang, Fei Huang, Guorong Jiang. Involvement of exogenous 3‑deoxyglucosone in β‑cell dysfunction induces impaired glucose regulation. Molecular medicine reports. 2017 Sep; 16(3):2976-2984. doi: 10.3892/mmr.2017.6856. [PMID: 28656301]
  • Aramesh Saremi, Scott Howell, Dawn C Schwenke, Gideon Bahn, Paul J Beisswenger, Peter D Reaven. Advanced Glycation End Products, Oxidation Products, and the Extent of Atherosclerosis During the VA Diabetes Trial and Follow-up Study. Diabetes care. 2017 Apr; 40(4):591-598. doi: 10.2337/dc16-1875. [PMID: 28148544]
  • Bas C T van Bussel, Marcel C G van de Poll, Casper G Schalkwijk, Dennis C J J Bergmans. Increased Dicarbonyl Stress as a Novel Mechanism of Multi-Organ Failure in Critical Illness. International journal of molecular sciences. 2017 Feb; 18(2):. doi: 10.3390/ijms18020346. [PMID: 28178202]
  • Fei Wang, Liang Zhou, Xiudao Song, Guoqiang Liang, Heng Xu, Lurong Zhang, Guorong Jiang. Acute Reduction of Incretin Effect and Glucose Intolerance in Rats by Single Intragastric Administration of 3-deoxyglucosone. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2017 Jan; 125(1):4-11. doi: 10.1055/s-0042-111684. [PMID: 27658000]
  • G Liang, X Song, H Xu, F Wang, L Zhang, L Zhou, G Jiang. 3-Deoxyglucosone Induced Acute Glucose Intolerance in Sprague-Dawley Rats: Involvement of Insulin Resistance and Impaired β-cell Function. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2016 Jul; 124(7):431-6. doi: 10.1055/s-0035-1565193. [PMID: 26824285]
  • Guoqiang Liang, Fei Wang, Xiudao Song, Lurong Zhang, Zhen Qian, Guorong Jiang. 3-Deoxyglucosone induces insulin resistance by impairing insulin signaling in HepG2 cells. Molecular medicine reports. 2016 May; 13(5):4506-12. doi: 10.3892/mmr.2016.5081. [PMID: 27052187]
  • Dionne E Maessen, Nordin M Hanssen, Jean L Scheijen, Carla J van der Kallen, Marleen M van Greevenbroek, Coen D Stehouwer, Casper G Schalkwijk. Post-Glucose Load Plasma α-Dicarbonyl Concentrations Are Increased in Individuals With Impaired Glucose Metabolism and Type 2 Diabetes: The CODAM Study. Diabetes care. 2015 May; 38(5):913-20. doi: 10.2337/dc14-2605. [PMID: 25710921]
  • Naila Rabbani, Paul J Thornalley. Dicarbonyl stress in cell and tissue dysfunction contributing to ageing and disease. Biochemical and biophysical research communications. 2015 Mar; 458(2):221-6. doi: 10.1016/j.bbrc.2015.01.140. [PMID: 25666945]
  • Tom Teichert, Anne Hellwig, Annette Peßler, Michael Hellwig, Mohammad Vossoughi, Dorothea Sugiri, Andrea Vierkötter, Thomas Schulte, Juliane Freund, Michael Roden, Barbara Hoffmann, Tamara Schikowski, Christian Luckhaus, Ursula Krämer, Thomas Henle, Christian Herder. Association between Advanced Glycation End Products and Impaired Fasting Glucose: Results from the SALIA Study. PloS one. 2015; 10(5):e0128293. doi: 10.1371/journal.pone.0128293. [PMID: 26018950]
  • Julia Degen, Helene Beyer, Björn Heymann, Michael Hellwig, Thomas Henle. Dietary influence on urinary excretion of 3-deoxyglucosone and its metabolite 3-deoxyfructose. Journal of agricultural and food chemistry. 2014 Mar; 62(11):2449-56. doi: 10.1021/jf405546q. [PMID: 24579887]
  • Jean L J M Scheijen, Casper G Schalkwijk. Quantification of glyoxal, methylglyoxal and 3-deoxyglucosone in blood and plasma by ultra performance liquid chromatography tandem mass spectrometry: evaluation of blood specimen. Clinical chemistry and laboratory medicine. 2014 Jan; 52(1):85-91. doi: 10.1515/cclm-2012-0878. [PMID: 23492564]
  • Guorong Jiang, Lurong Zhang, Qingling Ji, Fei Wang, Heng Xu, Fei Huang, Chunxiang Wang. Accumulation of plasma 3-deoxyglucosone impaired glucose regulation in Chinese seniors: implication for senile diabetes?. Diabetes & metabolic syndrome. 2012 Jul; 6(3):140-5. doi: 10.1016/j.dsx.2012.09.010. [PMID: 23158977]
  • Caatje Y le Poole, Frans J van Ittersum, Rob M Valentijn, Tom Teerlink, Bengt Lindholm, Piet M Ter Wee, Casper G Schalkwijk. "NEPP" peritoneal dialysis regimen has beneficial effects on plasma CEL and 3-DG, but not pentosidine, CML, and MGO. Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis. 2012 Jan; 32(1):45-54. doi: 10.3747/pdi.2010.00101. [PMID: 21632443]
  • Stefan Mittelmaier, Toshimitsu Niwa, Monika Pischetsrieder. Chemical and physiological relevance of glucose degradation products in peritoneal dialysis. Journal of renal nutrition : the official journal of the Council on Renal Nutrition of the National Kidney Foundation. 2012 Jan; 22(1):181-5. doi: 10.1053/j.jrn.2011.10.014. [PMID: 22200439]
  • Lian Engelen, Søren S Lund, Isabel Ferreira, Lise Tarnow, Hans-Henrik Parving, Jørgen Gram, Kaj Winther, Oluf Pedersen, Tom Teerlink, Rob Barto, Coen D A Stehouwer, Allan A Vaag, Casper G Schalkwijk. Improved glycemic control induced by both metformin and repaglinide is associated with a reduction in blood levels of 3-deoxyglucosone in nonobese patients with type 2 diabetes. European journal of endocrinology. 2011 Mar; 164(3):371-9. doi: 10.1530/eje-10-0851. [PMID: 21205874]
  • Kota Matsuki, Naoki Tamasawa, Maki Yamashita, Jutaro Tanabe, Hiroshi Murakami, Jun Matsui, Tadaatsu Imaizumi, Kei Satoh, Toshihiro Suda. Metformin restores impaired HDL-mediated cholesterol efflux due to glycation. Atherosclerosis. 2009 Oct; 206(2):434-8. doi: 10.1016/j.atherosclerosis.2009.03.003. [PMID: 19376519]
  • Meng-Yan Wu, Bud-Gen Chen, Chiung Dan Chang, Mei-Han Huang, Tai-Guang Wu, Daw-Ming Chang, Yau-Jiunn Lee, Hsiang Ching Wang, Chu-I Lee, Chi-Liang Chern, Ray H Liu. A novel derivatization approach for simultaneous determination of glyoxal, methylglyoxal, and 3-deoxyglucosone in plasma by gas chromatography-mass spectrometry. Journal of chromatography. A. 2008 Sep; 1204(1):81-6. doi: 10.1016/j.chroma.2008.07.040. [PMID: 18692194]
  • Martin Erixon, Anders Wieslander, Torbjörn Lindén, Ola Carlsson, Jan Ake Jönsson, Ole Simonsen, Per Kjellstrand. 3,4-DGE in peritoneal dialysis fluids cannot be found in plasma after infusion into the peritoneal cavity. Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis. 2008 May; 28(3):277-82. doi: 10.1177/089686080802800315. [PMID: 18474921]
  • François Collard, Didier Vertommen, Juliette Fortpied, Gregg Duester, Emile Van Schaftingen. Identification of 3-deoxyglucosone dehydrogenase as aldehyde dehydrogenase 1A1 (retinaldehyde dehydrogenase 1). Biochimie. 2007 Mar; 89(3):369-73. doi: 10.1016/j.biochi.2006.11.005. [PMID: 17175089]
  • Paul J Beisswenger, Keith S Drummond, Robert G Nelson, Scott K Howell, Benjamin S Szwergold, Michael Mauer. Susceptibility to diabetic nephropathy is related to dicarbonyl and oxidative stress. Diabetes. 2005 Nov; 54(11):3274-81. doi: 10.2337/diabetes.54.11.3274. [PMID: 16249455]
  • C Wihler, S Schäfer, K Schmid, E K Deemer, G Münch, M Bleich, A E Busch, T Dingermann, V Somoza, J W Baynes, J Huber. Renal accumulation and clearance of advanced glycation end-products in type 2 diabetic nephropathy: effect of angiotensin-converting enzyme and vasopeptidase inhibition. Diabetologia. 2005 Aug; 48(8):1645-53. doi: 10.1007/s00125-005-1837-9. [PMID: 16010524]
  • Yoshiaki Uchida, Yoshihiro Kurano, Tomohiro Endo, Misao Aoyama, Satoru Ito. Immunochemical detection of 3-deoxyglucosone in serum. Biochemical and biophysical research communications. 2004 Dec; 325(3):1090-8. doi: 10.1016/j.bbrc.2004.10.131. [PMID: 15541400]
  • Tadashi Jono, Ryoji Nagai, Xia Lin, Naila Ahmed, Paul J Thornalley, Motohiro Takeya, Seikoh Horiuchi. Nepsilon-(Carboxymethyl)lysine and 3-DG-imidazolone are major AGE structures in protein modification by 3-deoxyglucosone. Journal of biochemistry. 2004 Sep; 136(3):351-8. doi: 10.1093/jb/mvh124. [PMID: 15598892]
  • T R Brown, B Su, K A Brown, M A Schwartz, A M Tobia, F Kappler. Modulation of in vivo 3-deoxyglucosone levels. Biochemical Society transactions. 2003 Dec; 31(Pt 6):1433-7. doi: 10.1042/bst0311433. [PMID: 14641082]
  • William H Hoffman, Frank Kappler, Gregory G Passmore, Renuka Mehta. Diabetic ketoacidosis and its treatment increase plasma 3-deoxyglucosone. Clinical biochemistry. 2003 Jun; 36(4):269-73. doi: 10.1016/s0009-9120(03)00030-4. [PMID: 12810155]
  • Hitomi Kusunoki, Satoshi Miyata, Takeshi Ohara, Bing-Fen Liu, Atsuko Uriuhara, Hiroshi Kojima, Kotaro Suzuki, Hiroyuki Miyazaki, Yumiko Yamashita, Kayo Inaba, Masato Kasuga. Relation between serum 3-deoxyglucosone and development of diabetic microangiopathy. Diabetes care. 2003 Jun; 26(6):1889-94. doi: 10.2337/diacare.26.6.1889. [PMID: 12766129]
  • Martin Zeier, Vedat Schwenger, Reinhold Deppisch, Ulrike Haug, Kai Weigel, U Bahner, Christoph Wanner, H Schneider, Thomas Henle, Eberhard Ritz. Glucose degradation products in PD fluids: do they disappear from the peritoneal cavity and enter the systemic circulation?. Kidney international. 2003 Jan; 63(1):298-305. doi: 10.1046/j.1523-1755.2003.00705.x. [PMID: 12472796]
  • Yukiko Hasuike, Takeshi Nakanishi, Yoshinaga Otaki, Masayoshi Nanami, Tsuyoshi Tanimoto, Naoyuki Taniguchi, Yoshihiro Takamitsu. Plasma 3-deoxyglucosone elevation in chronic renal failure is associated with increased aldose reductase in erythrocytes. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2002 Sep; 40(3):464-71. doi: 10.1053/ajkd.2002.34884. [PMID: 12200796]
  • Reiko Inagi, Toshio Miyata, Yasuhiko Ueda, Atsushi Yoshino, Masaomi Nangaku, Charles van Ypersele de Strihou, Kiyoshi Kurokawa. Efficient in vitro lowering of carbonyl stress by the glyoxalase system in conventional glucose peritoneal dialysis fluid. Kidney international. 2002 Aug; 62(2):679-87. doi: 10.1046/j.1523-1755.2002.00488.x. [PMID: 12110033]
  • M Takeuchi, Y Yanase, N Matsuura, S Yamagishi Si, Y Kameda, R Bucala, Z Makita. Immunological detection of a novel advanced glycation end-product. Molecular medicine (Cambridge, Mass.). 2001 Nov; 7(11):783-91. doi: 10.1007/bf03401969. [PMID: 11788793]
  • S Mandl-Weber, B Haslinger, C G Schalkwijk, T Sitter. Early glycated albumin, but not advanced glycated albumin, methylglyoxal, or 3-deoxyglucosone increases the expression of PAI-1 in human peritoneal mesothelial cells. Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis. 2001 Sep; 21(5):487-94. doi: 10.1177/089686080102100510. [PMID: 11757833]
  • T Niwa, S Tsukushi. 3-deoxyglucosone and AGEs in uremic complications: inactivation of glutathione peroxidase by 3-deoxyglucosone. Kidney international. Supplement. 2001 Feb; 78(?):S37-41. doi: 10.1046/j.1523-1755.2001.59780037.x. [PMID: 11168980]
  • A Sakai, M Nakayama, M Numata, S Takesawa, M Nakamoto. Sodium sulfite and N-acetylcysteine: new additives to dialysate for inhibiting formation of glucose degradation products and advanced glycation end-products. Advances in peritoneal dialysis. Conference on Peritoneal Dialysis. 2001; 17(?):66-70. doi: NULL. [PMID: 11510300]
  • F Kappler, M L Schwartz, B Su, A M Tobia, T Brown. DYN 12, a small molecule inhibitor of the enzyme amadorase, lowers plasma 3-deoxyglucosone levels in diabetic rats. Diabetes technology & therapeutics. 2001; 3(4):609-16. doi: 10.1089/15209150152811234. [PMID: 11911173]
  • Y Ueda, T Miyata, E Goffin, A Yoshino, R Inagi, Y Ishibashi, Y Izuhara, A Saito, K Kurokawa, C Van Ypersele De Strihou. Effect of dwell time on carbonyl stress using icodextrin and amino acid peritoneal dialysis fluids. Kidney international. 2000 Dec; 58(6):2518-24. doi: 10.1046/j.1523-1755.2000.00436.x. [PMID: 11115086]
  • Y Hamada, J Nakamura, K Naruse, T Komori, K Kato, Y Kasuya, R Nagai, S Horiuchi, N Hotta. Epalrestat, an aldose reductase ihibitor, reduces the levels of Nepsilon-(carboxymethyl)lysine protein adducts and their precursors in erythrocytes from diabetic patients. Diabetes care. 2000 Oct; 23(10):1539-44. doi: 10.2337/diacare.23.10.1539. [PMID: 11023149]
  • Toshio Miyata, Yasuhiko Ueda, Koichi Asahi, Yuko Izuhara, Reiko Inagi, Akira Saito, Charles VAN Ypersele DE Strihou, Kiyoshi Kurokawa. Mechanism of the inhibitory effect of OPB-9195 [(+/-)-2-isopropylidenehydrazono-4-oxo-thiazolidin-5-yla cetanilide] on advanced glycation end product and advanced lipoxidation end product formation. Journal of the American Society of Nephrology : JASN. 2000 Sep; 11(9):1719-1725. doi: 10.1681/asn.v1191719. [PMID: 10966497]
  • P J Thornalley, A Langborg, H S Minhas. Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose. The Biochemical journal. 1999 Nov; 344 Pt 1(?):109-16. doi: . [PMID: 10548540]
  • H Odani, T Shinzato, Y Matsumoto, J Usami, K Maeda. Increase in three alpha,beta-dicarbonyl compound levels in human uremic plasma: specific in vivo determination of intermediates in advanced Maillard reaction. Biochemical and biophysical research communications. 1999 Mar; 256(1):89-93. doi: 10.1006/bbrc.1999.0221. [PMID: 10066428]
  • P J Beisswenger, S K Howell, A D Touchette, S Lal, B S Szwergold. Metformin reduces systemic methylglyoxal levels in type 2 diabetes. Diabetes. 1999 Jan; 48(1):198-202. doi: 10.2337/diabetes.48.1.198. [PMID: 9892243]
  • T Miyata, Y Ueda, Y Yamada, Y Izuhara, T Wada, M Jadoul, A Saito, K Kurokawa, C van Ypersele de Strihou. Accumulation of carbonyls accelerates the formation of pentosidine, an advanced glycation end product: carbonyl stress in uremia. Journal of the American Society of Nephrology : JASN. 1998 Dec; 9(12):2349-56. doi: 10.1681/asn.v9122349. [PMID: 9848790]
  • F Takayama, I Aoyama, S Tsukushi, T Miyazaki, S Miyazaki, T Morita, Y Hirasawa, K Shimokata, T Niwa. Immunohistochemical detection of imidazolone and N(epsilon)-(carboxymethyl)lysine in aortas of hemodialysis patients. Cellular and molecular biology (Noisy-le-Grand, France). 1998 Nov; 44(7):1101-9. doi: NULL. [PMID: 9846892]
  • G Münch, R Keis, A Wessels, P Riederer, U Bahner, A Heidland, T Niwa, H D Lemke, R Schinzel. Determination of advanced glycation end products in serum by fluorescence spectroscopy and competitive ELISA. European journal of clinical chemistry and clinical biochemistry : journal of the Forum of European Clinical Chemistry Societies. 1997 Sep; 35(9):669-77. doi: 10.1515/cclm.1997.35.9.669. [PMID: 9352229]
  • A Araki. [Oxidative stress and diabetes mellitus: a possible role of alpha-dicarbonyl compounds in free radical formation]. Nihon Ronen Igakkai zasshi. Japanese journal of geriatrics. 1997 Sep; 34(9):716-20. doi: NULL. [PMID: 9430981]
  • S Lal, F Kappler, M Walker, T J Orchard, P J Beisswenger, B S Szwergold, T R Brown. Quantitation of 3-deoxyglucosone levels in human plasma. Archives of biochemistry and biophysics. 1997 Jun; 342(2):254-60. doi: 10.1006/abbi.1997.0117. [PMID: 9186486]
  • T Niwa, T Katsuzaki, Y Ishizaki, F Hayase, T Miyazaki, T Uematsu, N Tatemichi, Y Takei. Imidazolone, a novel advanced glycation end product, is present at high levels in kidneys of rats with streptozotocin-induced diabetes. FEBS letters. 1997 May; 407(3):297-302. doi: 10.1016/s0014-5793(97)00362-1. [PMID: 9175872]
  • T Niwa. Beta2-Microglobulin dialysis amyloid and its formation: role of 3-deoxyglucosone and advanced glycation end products. Nephron. 1997; 76(4):373-91. doi: 10.1159/000190218. [PMID: 9274834]
  • R H Nagaraj, C Sady. The presence of a glucose-derived Maillard reaction product in the human lens. FEBS letters. 1996 Mar; 382(3):234-8. doi: 10.1016/0014-5793(96)00142-1. [PMID: 8605976]
  • T Niwa, T Katsuzaki, T Momoi, T Miyazaki, H Ogawa, A Saito, S Miyazaki, K Maeda, N Tatemichi, Y Takei. Modification of beta 2m with advanced glycation end products as observed in dialysis-related amyloidosis by 3-DG accumulating in uremic serum. Kidney international. 1996 Mar; 49(3):861-7. doi: 10.1038/ki.1996.119. [PMID: 8648931]
  • Y Hamada, N Araki, S Horiuchi, N Hotta. Role of polyol pathway in nonenzymatic glycation. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 1996; 11 Suppl 5(?):95-8. doi: 10.1093/ndt/11.supp5.95. [PMID: 9044317]
  • T Niwa, T Miyazaki, T Katsuzaki, N Tatemichi, Y Takei. Serum levels of 3-deoxyglucosone and tissue contents of advanced glycation end products are increased in streptozotocin-induced diabetic rats with nephropathy. Nephron. 1996; 74(3):580-5. doi: 10.1159/000189456. [PMID: 8938685]
  • M Portero-Otin, R H Nagaraj, V M Monnier. Chromatographic evidence for pyrraline formation during protein glycation in vitro and in vivo. Biochimica et biophysica acta. 1995 Feb; 1247(1):74-80. doi: 10.1016/0167-4838(94)00209-y. [PMID: 7873594]
  • M Takahashi, Y B Lu, T Myint, J Fujii, Y Wada, N Taniguchi. In vivo glycation of aldehyde reductase, a major 3-deoxyglucosone reducing enzyme: identification of glycation sites. Biochemistry. 1995 Jan; 34(4):1433-8. doi: 10.1021/bi00004a038. [PMID: 7827091]
  • T Niwa, N Takeda, T Miyazaki, H Yoshizumi, A Tatematsu, K Maeda, M Ohara, S Tomiyama, K Niimura. Elevated serum levels of 3-deoxyglucosone, a potent protein-cross-linking intermediate of the Maillard reaction, in uremic patients. Nephron. 1995; 69(4):438-43. doi: 10.1159/000188516. [PMID: 7777110]
  • H Yamada, S Miyata, N Igaki, H Yatabe, Y Miyauchi, T Ohara, M Sakai, H Shoda, M Oimomi, M Kasuga. Increase in 3-deoxyglucosone levels in diabetic rat plasma. Specific in vivo determination of intermediate in advanced Maillard reaction. The Journal of biological chemistry. 1994 Aug; 269(32):20275-80. doi: 10.1016/s0021-9258(17)31987-7. [PMID: 8051120]
  • K Sato, A Inazu, S Yamaguchi, T Nakayama, Y Deyashiki, H Sawada, A Hara. Monkey 3-deoxyglucosone reductase: tissue distribution and purification of three multiple forms of the kidney enzyme that are identical with dihydrodiol dehydrogenase, aldehyde reductase, and aldose reductase. Archives of biochemistry and biophysics. 1993 Dec; 307(2):286-94. doi: 10.1006/abbi.1993.1591. [PMID: 8274014]
  • K J Knecht, M S Feather, J W Baynes. Detection of 3-deoxyfructose and 3-deoxyglucosone in human urine and plasma: evidence for intermediate stages of the Maillard reaction in vivo. Archives of biochemistry and biophysics. 1992 Apr; 294(1):130-7. doi: 10.1016/0003-9861(92)90146-n. [PMID: 1550339]
  • H Kato, N van Chuyen, T Shinoda, F Sekiya, F Hayase. Metabolism of 3-deoxyglucosone, an intermediate compound in the Maillard reaction, administered orally or intravenously to rats. Biochimica et biophysica acta. 1990 Jul; 1035(1):71-6. doi: 10.1016/0304-4165(90)90175-v. [PMID: 2383581]
  • N Igaki, M Sakai, H Hata, M Oimomi, S Baba, H Kato. Effects of 3-deoxyglucosone on the Maillard reaction. Clinical chemistry. 1990 Apr; 36(4):631-4. doi: 10.1093/clinchem/36.4.631. [PMID: 2157564]
  • M Oimomi, N Igaki, T Ohara, M Sakai, T Nakamichi, F Hata, S Baba. Effect of aminoguanidine on the glycation. The Kobe journal of medical sciences. 1989 Dec; 35(5-6):255-9. doi: NULL. [PMID: 2635241]