GANT61
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MedKoo CAT#: 406570

CAS#: 500579-04-4

Description: GANT61 is a small-molecule inhibitor of glioma-associated oncogene 1 (GLI1)- and GLI2-mediated transcription at the nuclear level that exerts its effect by preventing DNA binding. It has been demonstrated to induce cell death against Ewing's sarcoma family tumor (ESFT) cell lines in a dose-dependent manner.


Chemical Structure

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GANT61
CAS# 500579-04-4

Theoretical Analysis

MedKoo Cat#: 406570
Name: GANT61
CAS#: 500579-04-4
Chemical Formula: C27H35N5
Exact Mass: 429.28925
Molecular Weight: 429.6
Elemental Analysis: C, 75.49; H, 8.21; N, 16.30

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 Same day
25.0mg USD 250.0 Same day
50.0mg USD 450.0 Same day
100.0mg USD 750.0 Same day
200.0mg USD 1250.0 Same day
500.0mg USD 2650.0 Same day
1.0g USD 4150.0 Same day
2.0g USD 6550.0 Same day
5.0g USD 9950.0 Ready to ship
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Synonym: GANT61; GANT-61; GANT 61; NSC 136476.

IUPAC/Chemical Name: 2,2'-((2-(pyridin-4-yl)dihydropyrimidine-1,3(2H,4H)-diyl)bis(methylene))bis(N,N-dimethylaniline)

InChi Key: KVQOGDQTWWCZFX-UHFFFAOYSA-N

InChi Code: InChI=1S/C27H35N5/c1-29(2)25-12-7-5-10-23(25)20-31-18-9-19-32(27(31)22-14-16-28-17-15-22)21-24-11-6-8-13-26(24)30(3)4/h5-8,10-17,27H,9,18-21H2,1-4H3

SMILES Code: CN(C)C1=CC=CC=C1CN2C(C3=CC=NC=C3)N(CC4=CC=CC=C4N(C)C)CCC2

Appearance: White to off-white 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: >2 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

Biological target: GANT 61 is an inhibitor of Gli1 and Gli2 targeting the Hedgehog/GLI pathway.
In vitro activity: In human colon carcinoma cells, treatment with the Gli small-molecule inhibitor GANT61 induces extensive cell death. GANT61 induced transient cellular accumulation at G(1)-S (24 hours) and in early S-phase (32 hours), with elevated p21(Cip1), cyclin E, and cyclin A in HT29 cells. GANT61 induced DNA damage within 24 hours, with the appearance of p-ATM and p-Chk2. Pharmacologic inhibition of Gli1 and Gli2 by GANT61 or genetic inhibition by transient transfection of the Gli3 repressor (Gli3R) downregulated Gli1 and Gli2 expression and induced γH2AX, PARP cleavage, caspase-3 activation, and cell death. GANT61 induced γH2AX nuclear foci, while transient transfection of Gli3R showed expression of Gli3R and γH2AX foci within the same nuclei in HT29, SW480, and HCT116. GANT61 specifically targeted Gli1 and Gli2 substantiated by specific inhibition of (i) direct binding of Gli1 and Gli2 to the promoters of target genes HIP1 and BCL-2, (ii) Gli-luciferase activity, and (iii) transcriptional activation of BCL-2. Taken together, these findings establish that inhibition of HH signaling at the level of the GLI genes downstream of Smo is critical in the induction of DNA damage in early S-phase, leading to cell death in human colon carcinoma cells. Reference: Cancer Res. 2011 Sep 1;71(17):5904-14. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/21747117/
In vivo activity: The 20 mg/kg GANT61 treatment reduced the incidence of collagen-induced arthritis (CIA) and relieved the arthritis symptoms in CIA rats. The Bcl-2 was upregulated and the Bax was downregulated in the CIA rats synovium. The 10 mg/kg and 20 mg/kg GANT61 diminished the Bcl-2 expression, 20 mg/kg GANT61 increased the Bax and activated the Caspases3 in the CIA synovium. The proliferation of CIA-FLS was significantly higher and the apoptosis of the CIA-FLS was lower than that of the control group. The 10 mg/kg and 20 mg/kg GANT61 treatment can reduce cell proliferation and induce apoptosis by diminishing Bcl-2 and increasing the Bax in CIA-FLS. Reference: J Orthop Sci. 2019 Mar;24(2):353-360. https://linkinghub.elsevier.com/retrieve/pii/S0949-2658(18)30248-3

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Ethanol 85.0 197.86

Preparing Stock Solutions

The following data is based on the product molecular weight 429.6 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
In vitro protocol: 1. Mazumdar T, Devecchio J, Agyeman A, Shi T, Houghton JA. Blocking Hedgehog survival signaling at the level of the GLI genes induces DNA damage and extensive cell death in human colon carcinoma cells. Cancer Res. 2011 Sep 1;71(17):5904-14. doi: 10.1158/0008-5472.CAN-10-4173. Epub 2011 Jul 11. PMID: 21747117; PMCID: PMC3165104. 2. Pan D, Li Y, Li Z, Wang Y, Wang P, Liang Y. Gli inhibitor GANT61 causes apoptosis in myeloid leukemia cells and acts in synergy with rapamycin. Leuk Res. 2012 Jun;36(6):742-8. doi: 10.1016/j.leukres.2012.02.012. Epub 2012 Mar 6. PMID: 22398221.
In vivo protocol: 1. Qin S, Sun D, Li X, Kong F, Yu Q, Hua H, Zheng K, Tang R. GANT61 alleviates arthritic symptoms by targeting fibroblast-like synoviocytes in CIA rats. J Orthop Sci. 2019 Mar;24(2):353-360. doi: 10.1016/j.jos.2018.09.003. Epub 2018 Sep 27. PMID: 30268354.

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1: Agyeman A, Jha BK, Mazumdar T, Houghton JA. Mode and specificity of binding of the small molecule GANT61 to GLI determines inhibition of GLI-DNA binding. Oncotarget. 2014 Jun 30;5(12):4492-503. PubMed PMID: 24962990; PubMed Central PMCID: PMC4147340.

2: Matsumoto T, Tabata K, Suzuki T. The GANT61, a GLI inhibitor, induces caspase-independent apoptosis of SK-N-LO cells. Biol Pharm Bull. 2014;37(4):633-41. PubMed PMID: 24694609.

3: Pan D, Li Y, Li Z, Wang Y, Wang P, Liang Y. Gli inhibitor GANT61 causes apoptosis in myeloid leukemia cells and acts in synergy with rapamycin. Leuk Res. 2012 Jun;36(6):742-8. doi: 10.1016/j.leukres.2012.02.012. Epub 2012 Mar 6. PubMed PMID: 22398221.

GANT61

10.0mg / USD 150.0


Additional Information