D-3-Deoxyglucosone

Names

[ Name ]:
D-3-Deoxyglucosone

[Synonym ]:
3-Deoxy-D-erythro-hexos-2-ulose
3-Deoxyglucosone
3-Deoxy-D-erythro-hexosulose
(4S,5R)-4,5,6-trihydroxy-2-oxohexanal
D-erythro-Hexos-2-ulose, 3-deoxy-

Biological Activity

[Description]:

3-Deoxyglucosone (3-Deoxy-D-glucosone) is a reactive intermediate of the Maillard reaction and the polyol pathway. 3-Deoxyglucosone rapidly reacts with protein amino groups to form advanced glycation end products (AGEs), such as imidazolone, it is the most specific AGE for 3-DG. 3-Deoxyglucosone synergizes with low glucose to potentiate GLP-1 secretion and is considered as a biomarker for diabetes[1][2][3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[In Vitro]

3-Deoxyglucosone (80 ng/ml-1000 ng/ml; 1 hour) markedly increases GLP-1 secretion by 1.23-folds in 300 ng/ml or 1000 ng/ml 3DG-treated group. But at alower concentration (80 ng/ml) has no effects[1]. 3-Deoxyglucosone (300 ng/ml; 1 hour) dramatically increases intracellular Ca2+ levels by Fluo-3/AM determination (2.5 μM for 30 mins). But 3DG does not affect intracellular cAMP levels in a cAMP Elisa assay[1]. 3-Deoxyglucosone (300 ng/ml; 1 hour) significantly increases the protein expression levels of TAS1R2, TAS1R3, and TRPM5 under both glucose-free and highconditions[1]. Western Blot Analysis[1] Cell Line: STC-1 cells Concentration: 300 ng/ml Incubation Time: 1 hour Result: Upregulated TAS1R2, TAS1R3, and TRPM5 expression.

[In Vivo]

3-Deoxyglucosone (intragastric administration; 20 mg/kg; single dose) impairs glucose tolerance with increased AUC, but the plasma glucagon levels are not significantly different. It developes impaired glucose regulation (IGR) with obviously pancreatic islet cell dysfunction in kunming mice and SD-rats[2]. 3-deoxyglucosone (gastric gavage; 5-50 mg/kg; once daily; 2 weeks) is significantly increased in the upper small intestine (1.4-fold), lower small intestine (1.4-fold), ileum (1.4-fold) and colon (two fold) compared with the basal levels in the corresponding control group. In addition, the protein expressions of TAS1R2, TAS1R3 and TRPM5 in both duodenum and colon are significantly decreased[3]. Animal Model: SD rats[3] Dosage: 5, 20 and 50 mg/kg Administration: oral administration; once daily; 2 weeks Result: Was capable of accumulating in intestinal tissue and thereby decreased secretion of GLP-1 and insulin.

[References]

[1]. Song X, et al. 3-Deoxyglucosone Induces Glucagon-Like Peptide-1 Secretion from STC-1 Cells via Upregulating Sweet Taste Receptor Expression under Basal Conditions.Int J Endocrinol. 2019 Oct 23;2019:4959646.

[2]. Wang F, et al. Acute Reduction of Incretin Effect and Glucose Intolerance in Rats by Single Intragastric Administration of 3-deoxyglucosone. Exp Clin Endocrinol Diabetes. 2017 Jan;125(1):4-11.

[3]. Zhang L, et al. Accumulation of intestinal tissue 3-deoxyglucosone attenuated GLP-1 secretion and its insulinotropic effect in rats. Diabetol Metab Syndr. 2016 Nov 29;8:78.

[4]. Niwa T, et al. 3-Deoxyglucosone: metabolism, analysis, biological activity, and clinical implication.J Chromatogr B Biomed Sci Appl. 1999 Aug 6;731(1):23-36.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
400.1±45.0 °C at 760 mmHg

[ Melting Point ]:
73-75ºC

[ Molecular Formula ]:
C₆H₁₀O₅

[ Molecular Weight ]:
162.141

[ Flash Point ]:
209.9±25.2 °C

[ Exact Mass ]:
162.052826

[ PSA ]:
94.83000

[ LogP ]:
-2.38

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.512

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MQ3390000

CHEMICAL NAME :: D-erythro-Hexosulose, 3-deoxy-

CAS REGISTRY NUMBER :: 4084-27-9

LAST UPDATED :: 199712

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C6-H10-O5

MOLECULAR WEIGHT :: 162.16

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 2 gm/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 227,117,1989

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Articles

3-Deoxyglucosone: a potential glycating agent accountable for structural alteration in H3 histone protein through generation of different AGEs.

PLoS ONE 10(2) , e0116804, (2015)

Advanced glycation end-products (AGEs) are heterogeneous group of compounds, known to be implicated in diabetic complications. One of the consequences of the Maillard reaction is attributed to the pro...

Studies on the Formation of Maillard and Caramelization Products from Glucosamine Incubated at 37 °C.

J. Agric. Food Chem. 63 , 6249-61, (2015)

This experiment compared the in vitro degradation of glucosamine (GlcN), N-acetylglucosamine, and glucose in the presence of NH3 incubated at 37 °C in phosphate buffer from 0.5 to 12 days. The reactio...

GC-MS Method for the Quantitation of Carbohydrate Intermediates in Glycation Systems.

J. Agric. Food Chem. 63 , 5911-9, (2015)

Glycation is a ubiquitous nonenzymatic reaction of carbonyl compounds with amino groups of peptides and proteins, resulting in the formation of advanced glycation end-products (AGEs) and thereby affec...