356790

Glyphosine

A plant growth regulator that also enhances anti-B:9-23 TCR-dependent T cell activation by modulating murine class II MHC I-Ag7-mediated B:9-23 presentation on APCs.

• Synonym(s): Glyphosine, Cp41845, N,N-bis(Phosphonomethyl)glycine, 2-(bis(Phosphonomethyl)amino)acetic acid, Polaris, Cp41845, Polaris, N,N-bis(Phosphonomethyl)glycine, 2-(bis(Phosphonomethyl)amino)acetic acid
• Empirical Formula (Hill Notation): C₄H₁₁NO₈P₂
• CAS Number: 2439-99-8
• Molecular Weight: 263.08
• MDL number: MFCD00056670
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• Assay: ≥98% (NMR)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; desiccated (hygroscopic); protect from light
• color: white
• solubility: water: 100 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• InChI: 1S/C4H11NO8P2/c6-4(7)1-5(2-14(8,9)10)3-15(11,12)13/h1-3H2,(H,6,7)(H2,8,9,10)(H2,11,12,13)
• InChI key: OXHDYFKENBXUEM-UHFFFAOYSA-N

Description

General description

A glycine-phosphonic acid compound, negatively charged at neutral pH, with immunomodulatory and anti-diabetic properties. Shown to enhance CD4⁺ T cell response to B-chain of insulin (amino acids 9-23) even at 10 nM levels (EC₅₀ = 70.6 nM). Occupies a pocket 9 of I-A^g7 (the class II molecules of the diabetes-prone NOD mice) and alters TCR/peptide-MHC affinity. Stimulates IL-10 secretion in splenocyes in non-obese diabetic (NOD) mice. Daily administration of glyphosine is shown to delay the onset of diabetes in NOD mice. Acts as a competitive inhibitor of phoshoenolpyruvate carboxylase in plants.

A plant growth regulator that also enhances anti-B:9-23 (aa 9 to 23 of insulin B chain) TCR-dependent T cell activation (EC₅₀ = 70.6 nM; EC_max = 500 nM) by modulating murine class II MHC I-A^g7-mediated B:9-23 presentation on APCs, without affecting the activation of anti-chromogranin T cells by chromogranin- I-A^g7 complex. Reported to augment B:9-23 in stimulating IL-10 production from splenocytes of diabetic NOD mice and PBMCs of type 1 diabetic individuals with HLA-DQ8, and effectively prevent the onset of diabetes in NOD mice (80 mg/kg via daily i.p.). Computer structural docking analysis indicates pocket 9 of the I-A^g7 binding groove as the glyphosine targeting site.

Packaging

Packaged under inert gas

Warning

Toxicity: Corrosive (L)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 year at -20°C.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.

Michels, A.W., et al. 2011. J. Immunol.187, 5921.
Stadinski, B.D., et al. 2010. Proc. Natl. Acad. Sci. USA107, 10978.
Podesta, F.E., et al. 1987. Plant Cell Physiol.28, 375.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H318
• Precautionary Statements: P280 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable