TH-237A (also known as meso-GS 164) is a novel and potent neuroprotective agent exhibiting favorable permeation across the blood brain barrier. TH-237A has neuroprotective properties against β-amyloid (Aβ)-induced neurodegeneration associated with Alzheimer's disease. Exposure of neuronal cultures to Aβ peptide in the presence of 5 nM TH-237A resulted in a 50% increase in survival. Neuronal cultures treated with other toxic stimuli such as staurosporine, thapsigargin, paraquat and H2O2 showed significantly enhanced survival in the presence of TH-237A . Microtubule binding and tubulin assembly studies revealed differences compared to paclitaxel, but confirmed the interaction of TH-237A with microtubules.

Physicochemical Properties

Molecular Formula	C18H17F2NO3
Molecular Weight	333.329292058945
Exact Mass	333.117
CAS #	935467-97-3
PubChem CID	16722711
Appearance	White to off-white solid powder
Density	1.4±0.1 g/cm3
Boiling Point	455.5±45.0 °C at 760 mmHg
Melting Point	90 °C (hexane)
Flash Point	229.3±28.7 °C
Vapour Pressure	0.0±1.2 mmHg at 25°C
Index of Refraction	1.626
LogP	4.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Heavy Atom Count	24
Complexity	402
Defined Atom Stereocenter Count	2
SMILES	C([C@@]12CO[C@@H](C3C=CC(F)=CC=3)N1[C@@H](C1C=CC(F)=CC=1)OC2)O
InChi Key	AEZQGSQEXPUADE-JWTNVVGKSA-N
InChi Code	InChI=1S/C18H17F2NO3/c19-14-5-1-12(2-6-14)16-21-17(13-3-7-15(20)8-4-13)24-11-18(21,9-22)10-23-16/h1-8,16-17,22H,9-11H2/t16-,17+,18?
Chemical Name	((3R,5S,7as)-3,5-bis(4-fluorophenyl)tetrahydro-1H-oxazolo[3,4-c]oxazol-7a-yl)methanol.
Synonyms	TH237A; TH 237A; TH237A; mesoGS 164.
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

Kelly E. Desino, Improving Blood Brain Barrier Permeation of Small Molecules Exhibiting Chemotherapeutic and Neuroprotective Effects.

Solubility Data

Solubility (In Vitro)

Ethanol : ~100 mg/mL (~300.00 mM) DMSO : ≥ 46 mg/mL (~138.00 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.50 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.50 mM) (saturation unknown) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.50 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.0000 mL	15.0002 mL	30.0003 mL
	5 mM	0.6000 mL	3.0000 mL	6.0001 mL
	10 mM	0.3000 mL	1.5000 mL	3.0000 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.