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Key Documents

5.09665

Sigma-Aldrich

Glucokinase Activator III, Ro-28-1675

Synonym(s):

Glucokinase Activator III, Ro-28-1675, GK Activator III, Hexokinase D Activator III, Hexokinase IV Activator III, Ro-28-0450 ( R)-enantiomer, RO0281675, GK Activator III, Hexokinase D Activator III, Hexokinase IV Activator III, Ro-28-0450 (R)-enantiomer, RO0281675

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About This Item

Empirical Formula (Hill Notation):
C18H22N2O3S2
CAS Number:
Molecular Weight:
378.51
UNSPSC Code:
51111800
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: 100 mg/mL

storage temp.

2-8°C

InChI

1S/C18H22N2O3S2/c1-25(22,23)15-8-6-14(7-9-15)16(12-13-4-2-3-5-13)17(21)20-18-19-10-11-24-18/h6-11,13,16H,2-5,12H2,1H3,(H,19,20,21)/t16-/m1/s1

InChI key

NEQSWPCDHDQINX-MRXNPFEDSA-N

General description

A cell-permeable thiazolyl-propanamide compound that acts as a glucokinase (GK) activator by increasing Vmax and decreasing [S]1/2 of GK-catalyzed reaction as well as freeing GK from the inhibitory action of GK regulatory protein (GKRP), resulting in increased. Induces GK nuclear-to-cytosol translocation in primary rat hepatocytes and reduces glucose concentration for insulin secretion stimulation from isolated rat pancreatic islets (threshold [glucose] = 3 mM vs 6 mM with or without 3 µM Ro-28-1675). Exhibits in vivo glucose-lowering and insulin-releasing activity in non-diabetic C57BL/6 mice and Wistar rats and is efficacious in several murine and rodent type II diabetes mellitus (T2DM) models (10 to 50 mg/kg via p.o.). Does not affect hexokinase I or II activity.
A cell-permeable thiazolyl-propanamide compound that acts as an allosteric glucokinase-(GK) selective activator, increasing Vmax and decreasing [S]1/2 (by 1.5- and 4.3-fold, respectively, at 3 µM; [Glucose] = 5 mM) in human GK enzymatic assays, as well as freeing GK from the inhibitory action of GK regulatory protein (GKRP), resulting in increased GK nuclear-to-cytosol translocation in primary rat hepatocytes (EC50/[Glucose] = 0.16 µM/16.8 mM, 0.27 µM/8.4 mM, 2.2 µM/2.8 mM) and reduced glucose concentration for stimulating insulin secretion from isolated rat pancreatic islets (threshold [glucose] = 3 mM vs 6 mM with or without 3 µM Ro-28-1675). Exhibits in vivo glucose-lowering and insulin-releasing activity in non-diabetic C57BL/6 mice and Wistar rats and is efficacious in several murine (KK/Upj-Ay/J, ob/ob, and diet-induced obese C57BL/6) and rodent (Goto-Kakizaki) type II diabetes mellitus (T2DM) models (10 to 50 mg/kg via p.o.), while efficacy is no longer observed in older hypoinsulinemic db/db mice with blood glucose levels reaching 300 mg/dl. Reported not to affect the activity of hexokinase I or II and display no activity toward GK-independent insulin release from β cells upon 2-Ketoisocaproic acid (α-KIC) stimulation.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Glucokinase
Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Wolff, M., et al. 2008. J. Biomol. Screen13, 837.

Grimsby, J., et al. 2003. Science301, 370.

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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