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373403

Sigma-Aldrich

Hh/Gli Antagonist, GANT61

InSolution, ≥95%

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Synonym(s):
InSolution Hh/Gli Antagonist, GANT61, 2,2ʹ-(2-(Pyridin-4-yl)dihydropyrimidine-1,3(2H,4H)-diyl) bis(methylene) bis(N,N-dimethylaniline), NSC 136476, 2-((3-(2-(Dimethylamino)benzyl)-2-(4-pyridinyl)tetrahydro-1(2H)-pyrimidinyl)methyl)-N,N-dimethylaniline
Empirical Formula (Hill Notation):
C27H35N5
CAS Number:
500579-04-4
Molecular Weight:
429.60
MDL number:
MFCD14635408
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
avoid repeated freeze/thaw cycles
desiccated (hygroscopic)
protect from light

shipped in

dry ice

storage temp.

−20°C

SMILES string

CN(C)C1=CC=CC=C1CN2CCCN(CC3=CC=CC=C3N(C)C)C2C4=CC=NC=C4

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

InChI key

KVQOGDQTWWCZFX-UHFFFAOYSA-N

General description

A cell-permeable hexahydropyrimidine compound that displays similar pharmacological property as, but is structurally disctinct from, GANT58 (>Cat. No. 373400). While both compounds act as downstream Hedgehog (Hh) pathway-selective blockers and target Gli-mediated gene transactivation with similar potency (IC50 ~5 µM) in SAG-stimulated Shh-L2 cells, GANT61 does exhibit better in vivo antitumor efficacy, presumably due to its superior pharmacokinetics, and only GANT61, but not GANT58, is shown to inhibit Gli DNA binding in HEK293 cells. The solid form of this compound (Cat. No. 373401) is also available.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Gli1 and Gli2

Packaging

Packaged under inert gas

Warning

Toxicity: Irritant (B)

Physical form

A 25 mM (2 mg/186 µL) solution of Hh/Gli Antagonist, GANT61 (Cat. No. 373401) in DMSO.

Legal Information

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

WGK

WGK 2

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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Matthias Lauth et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(20), 8455-8460 (2007-05-15)
The developmentally important Hedgehog (Hh) signaling pathway has recently been implicated in several forms of solid cancer. Current drug development programs focus on targeting the protooncogene Smoothened, a key transmembrane pathway member. These drug candidates, albeit promising, do not address

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