GANT58
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 500810

CAS#: 64048-12-0

Description: GANT58 is a cell-permeable tetrapyridinylthiophene compound that acts as downstream Hedgehog (Hh) pathway blocker and targets Gli-mediated gene transactivation (IC50 ~ 5 µM in SAG-stimulated Shh-L2 cells).


Chemical Structure

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GANT58
CAS# 64048-12-0

Theoretical Analysis

MedKoo Cat#: 500810
Name: GANT58
CAS#: 64048-12-0
Chemical Formula: C24H16N4S
Exact Mass: 392.10957
Molecular Weight: 392.47564
Elemental Analysis: C, 73.45; H, 4.11; N, 14.28; S, 8.17

Price and Availability

Size Price Availability Quantity
5.0mg USD 355.0 2 Weeks
Bulk inquiry

Synonym: GANT58; GANT 58; GANT-58.

IUPAC/Chemical Name: 2,3,4,5-Tetra(4-pyridyl)thiophene

InChi Key: USWLOKMMUTWFMD-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H16N4S/c1-9-25-10-2-17(1)21-22(18-3-11-26-12-4-18)24(20-7-15-28-16-8-20)29-23(21)19-5-13-27-14-6-19/h1-16H

SMILES Code: C1(C2=CC=NC=C2)=C(C3=CC=NC=C3)C(C4=CC=NC=C4)=C(C5=CC=NC=C5)S1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: GANT 58 (NSC 75503) is a potent GLI antagonist that inhibits GLI1-induced transcription with IC50 of 5 μM.
In vitro activity: To test this, this study exposed the ESFT cell line A673 to GANT58 at doses shown to inhibit GLI1 transactivation. Figure 5D demonstrates the anticipated transcriptional downregulation of Patched, NKX2.2 and GAS1 by treatment with GANT58. Reference: PLoS One. 2009 Oct 27;4(10):e7608. https://pubmed.ncbi.nlm.nih.gov/19859563/
In vivo activity: Substantial osteolytic lesions were observed radiographically in the mice treated only with the Empty-NPs (nanoparticles) after 4 weeks, while smaller and fewer lesions were visible in mice treated with GANT58-NP (Fig. 7B). Quantitative assessment of both lesion area and number confirmed that the osteolytic lesions in the GANT58-NP-treated mice were significantly smaller and fewer (Fig. 7C–D). Reference: J Control Release. 2019 Oct;311-312:257-272. https://pubmed.ncbi.nlm.nih.gov/31494183/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 2.5 6.37
DMF:PBS (pH 7.2) (1:1) 0.5 1.27
DMSO 10.05 25.59
Ethanol 10.7 27.26

Preparing Stock Solutions

The following data is based on the product molecular weight 392.47564 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Joo J, Christensen L, Warner K, States L, Kang HG, Vo K, Lawlor ER, May WA. GLI1 is a central mediator of EWS/FLI1 signaling in Ewing tumors. PLoS One. 2009 Oct 27;4(10):e7608. doi: 10.1371/journal.pone.0007608. PMID: 19859563; PMCID: PMC2763206. 2. Beauchamp E, Bulut G, Abaan O, Chen K, Merchant A, Matsui W, Endo Y, Rubin JS, Toretsky J, Uren A. GLI1 is a direct transcriptional target of EWS-FLI1 oncoprotein. J Biol Chem. 2009 Apr 3;284(14):9074-82. doi: 10.1074/jbc.M806233200. Epub 2009 Feb 3. PMID: 19189974; PMCID: PMC2666556. 3. Vanderburgh JP, Kwakwa KA, Werfel TA, Merkel AR, Gupta MK, Johnson RW, Guelcher SA, Duvall CL, Rhoades JA. Systemic delivery of a Gli inhibitor via polymeric nanocarriers inhibits tumor-induced bone disease. J Control Release. 2019 Oct;311-312:257-272. doi: 10.1016/j.jconrel.2019.08.038. Epub 2019 Sep 5. PMID: 31494183; PMCID: PMC7007697. 4. Chen X, Shi C, Cao H, Chen L, Hou J, Xiang Z, Hu K, Han X. The hedgehog and Wnt/β-catenin system machinery mediate myofibroblast differentiation of LR-MSCs in pulmonary fibrogenesis. Cell Death Dis. 2018 May 29;9(6):639. doi: 10.1038/s41419-018-0692-9. PMID: 29844390; PMCID: PMC5974360.
In vitro protocol: 1. Joo J, Christensen L, Warner K, States L, Kang HG, Vo K, Lawlor ER, May WA. GLI1 is a central mediator of EWS/FLI1 signaling in Ewing tumors. PLoS One. 2009 Oct 27;4(10):e7608. doi: 10.1371/journal.pone.0007608. PMID: 19859563; PMCID: PMC2763206. 2. Beauchamp E, Bulut G, Abaan O, Chen K, Merchant A, Matsui W, Endo Y, Rubin JS, Toretsky J, Uren A. GLI1 is a direct transcriptional target of EWS-FLI1 oncoprotein. J Biol Chem. 2009 Apr 3;284(14):9074-82. doi: 10.1074/jbc.M806233200. Epub 2009 Feb 3. PMID: 19189974; PMCID: PMC2666556.
In vivo protocol: 1. Vanderburgh JP, Kwakwa KA, Werfel TA, Merkel AR, Gupta MK, Johnson RW, Guelcher SA, Duvall CL, Rhoades JA. Systemic delivery of a Gli inhibitor via polymeric nanocarriers inhibits tumor-induced bone disease. J Control Release. 2019 Oct;311-312:257-272. doi: 10.1016/j.jconrel.2019.08.038. Epub 2019 Sep 5. PMID: 31494183; PMCID: PMC7007697. 2. Chen X, Shi C, Cao H, Chen L, Hou J, Xiang Z, Hu K, Han X. The hedgehog and Wnt/β-catenin system machinery mediate myofibroblast differentiation of LR-MSCs in pulmonary fibrogenesis. Cell Death Dis. 2018 May 29;9(6):639. doi: 10.1038/s41419-018-0692-9. PMID: 29844390; PMCID: PMC5974360.

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GANT58

5.0mg / USD 355.0


Additional Information