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Catalog No.: GC41224

A glutaminase inhibitor

6-diazo-5-oxo-L-nor-Leucine Chemical Structure

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Sample solution is provided at 25 µL, 10mM.

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6-Diazo-5-oxo-L-nor-Leucine (DON) is a glutamine analog that inhibits glutaminases (Ki = 6 µM) and other glutamine-utilizing enzymes, including cytidine triphosphate synthase (CTPS), which uses glutamine in the synthesis of CTP.[1],[2],[3] DON is commonly used in cells or tissues but its use in whole animals is limited by its teratogenicity.[3],[4],[5]

[1]. Willis, R.C., and Seegmiller, J.E. The inhibition by 6-diazo-5-oxo-l-norleucine of glutamine catabolism of the cultured human lymphoblast. J.Cell Physiol. 93, 375-382 (1977).
[2]. Thangavelu, K., Chong, Q.Y., Low, B.C., et al. Structural basis for the active site inhibition mechanism of human kidney-type glutaminase (KGA). Sci.Rep. 4, 1-7 (2014).
[3]. Thomas, A.G., Rojas, C., Tanega, C., et al. Kinetic characterization of ebselen, chelerythrine and apomorphine as glutaminase inhibitors. Biochemical and Biophysical Research Communications 438(2), 243-248 (2013).
[4]. Botman, D., Tigchelaar, W., and Van Noorden, C.J.F. Determination of phosphate-activated glutaminase activity and its kinetics in mouse tissues using metabolic mapping (quantitative enzyme histochemistry). Journal of Histochemistry and Cytochemistry 62(11), 813-826 (2014).
[5]. Greene, R.M., and Kochhar, D.M. Limb development in mouse embryos: Protection against teratogenic effects of 6-diazo-5-ox-L-norleucine (DON) in vivo and in vitro. J.Embryol.Exp.Morphol. 33(2), 355-370 (1975).

Chemical Properties

Cas No. 157-03-9 SDF
Synonyms DON, NSC 7365
Chemical Name 6-diazo-5-oxo-L-norleucine
Canonical SMILES OC([C@@H](N)CCC(C=[N+]=[N-])=O)=O
Formula C6H9N3O3 M.Wt 171.2
Solubility >1mg/mL in DMSO, >10mg/mL in Water(Need warm the tube at 50 ℃ and shake it in the ultrasonic bath for a while) Storage Store at -20°C,protect from light, stored under nitrogen
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request

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Research Update

The control of adrenocortical cytodifferentiation by extracellular matrix

Differentiation 1980;17(2):93-103.PMID:6256247DOI:10.1111/j.1432-0436.1980.tb01085.x

Adult rat adrenal cortical cells maintained in medium supplemented with horse serum (HS) from cohesive epithelial islands secrete large amounts of corticosterone. Such cells do not produce detectable extracellular material (ECM) and are not motile. Cultures exposed to fetal calf serum supplements (FCS) produce metachromatic ECM, modulate to a fibroblastic morphology, and become motile. Within 24 h, steroid production by these cells drop 100-fold. Cells now resemble myofibroblastic "stem" cells of the adrenal cortical capsule, and express structural and functional bimorphism by exhibiting a myofibroblastic phenotype while retaining responsiveness to adrenocorticotropic hormone (ACTH) and limited corticosteroid secreting capacity. Exposure of the myofibroblastic cells to ACTH in FCS overrides the effect of FSC: ECM disappears, steroid production increases several fold, and cells develop an epithelial morphology. The possibility that ECM produced in response to FCS may be responsible for the alteration from a highly differentiated, non-motile adrenocortical cell to a less differentiated, motile adrenocortical stem cell was investigated by inhibition studies using 6-diazo-5-oxo-L-nor-Leucine (DON) and by exogenously added components of ECM. DON, a glutamine analogue, inhibited the synthesis of metachromatic ECM in FCS, and prevented the modulation to a fibroblastic morphology, onset of motility, and decrease in steroid production. Addition of hyaluronic acid, but not of chondroitin sulfate, to the epithelioid secretory cells promoted a drop in steroid production and slight alteration in morphology and movement. Both results are consistent with the possibility that metachromatic ECM production is responsible for the reversion of the steroid secretory to the myofibroblastic phenotype. This effect was mimicked by maintaining cells on polystyrene surfaces that were sulfonated to a negative charge density similar to that of ECM. This result implies that the negative charge of ECM may contribute to the expression of the adrenocortical stem cell phenotype, and that its effect is extracellular. A possible physiologic role for ECM-mediated control of adrenal cortical differentiation is proposed.


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