SMART

Alias: (2-Phenyl-thiazol-4-yl)-(3,4,5-trimethoxy-phenyl)-methanone
Cat No.:V3031 Purity: ≥98%
SMART is a highly potent tubulin inhibitor with IC50 in the nanomolar range (20-30 nM) in a number various cancer cell lines including prostate cancer and melanoma cells.
SMART Chemical Structure CAS No.: 1135797-91-9
Product category: Microtubule Associated
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

SMART is a highly potent tubulin inhibitor with IC50 in the nanomolar range (20-30 nM) in a number various cancer cell lines including prostate cancer and melanoma cells. It is discovered by Dr. Duane D Miller's group in the University of Tennessee Health Science Center based on the structure of 2-aryl-thiazolidine-4-carboxylic acid amides (ATCAA), a chemical scaffold designed from lysophosphatidic acid (LPA) with a lipid chain in order to inhibit guanine-binding protein-coupled receptor (GPCR) signaling, which was involved in proliferation and survival of prostate cancer. SMART exerts the anticancer activity by binding to the colchicine binding site of tubulin and inhibiting the polymerization of microtubules, thereby resulting in the inhibition of cell division.

Biological Activity I Assay Protocols (From Reference)
ln Vitro

In vitro activity: Bovine brain tubulin (0.4 mg) (Cytoskeleton, Denver, CO) was mixed with various concentrations (0.625-20 μM) of test compound and incubated in 120 μL of general tubulin buffer (80 mM PIPES, 2.0 mM MgCl2, 0.5 mM EGTA, pH 6.9, and 1 mM GTP). The absorbance of wavelength at 340 nm was monitored every 60 s for 20 min by the SYNERGY 4 microplate reader (Bio-Tek Instruments, Winooski, VT). The spectrophotometer was set at 37 °C for tubulin polymerization. The IC50 value was defined as the concentration which can inhibit 50% of microtubule polymerization.


Cell Assay: Cell Culture and Cytotoxicity Assay of Melanoma. We examined the antiproliferative activity of the ATCAA and SMART analogues in one human melanoma cell line (A375) and one mouse melanoma cell line (B16-F1). We used activity on fibroblast cells as a control to determine the selectivity of these compounds against melanoma. A375 cells and B16-F1 cells were purchased from ATCC (American Type Culture Collection, Manassas, VA). Human dermal fibroblast cells were purchased from Cascade Biologics, Inc., Portland, OR. All cell lines were cultured in DMEM (Cellgro Mediatech, Inc., Herndon, VA), supplemented with 5% FBS (Cellgro Mediatech), 1% antibiotic/antimycotic mixture (Sigma-Aldrich, Inc., St. Louis, MO), and bovine insulin (5 μg/mL; Sigma-Aldrich). Cultures were maintained at 37 °C in a humidified atmosphere containing 5% CO2. Standard sulforhodamine B assay was used. Cells were exposed to a wide range of concentrations for 48 h in round-bottomed 96-well plates. Cells were fixed with 10% trichloroacetic acid and washed five times with water. After cells were air-dried overnight and stained with SRB solution, total proteins were measured at 560 nm with a plate reader. IC50 (i.e., concentration which inhibited cell growth by 50% of no treatment controls) values were obtained by nonlinear regression analysis with GraphPad Prism (GraphPad Software, San Diego,CA).

ln Vivo

Animal Protocol


References
2009 Mar 26;52(6):1701-11;2011 Jul 14;54(13):4678-93.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H17NO4S
Molecular Weight
355.408
CAS #
1135797-91-9
Synonyms
(2-Phenyl-thiazol-4-yl)-(3,4,5-trimethoxy-phenyl)-methanone
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)
Solubility Data
Solubility (In Vitro)
DMSO: soluble (>10 mM)
Water:<1 mg/mL
Ethanol:<1 mg/mL
Solubility (In Vivo)
N/A
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.8137 mL 14.0683 mL 28.1365 mL
5 mM 0.5627 mL 2.8137 mL 5.6273 mL
10 mM 0.2814 mL 1.4068 mL 2.8137 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.

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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • SMART

    Structures ofLPA, ATCAAandSMART.2009 Mar 26;52(6):1701-11.

  • SMART

    Effect of8fon tubulin assembly.2009 Mar 26;52(6):1701-11.

  • SMART

    SAR relationship of the SMART molecules.2009 Mar 26;52(6):1701-11.

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