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5.31066

Sigma-Aldrich

Remodelin

Synonym(s):

Remodelin, Cyclopentylidene-(4-(4-cyanophenyl)thiazol-2-yl)hydrazine, HBr, 4-(4-Chlorophenyl)-2-(2-cyclopentylidenehydrazinyl)thiazole, HBr, 4-(2-(2-Cyclopentylidenehydrazino)-1,3-thiazol-4-yl)benzonitrile, HBr

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About This Item

Empirical Formula (Hill Notation):
C15H14N4S · xHBr
CAS Number:
1622921-15-6
Molecular Weight:
282.36 (free base basis)
UNSPSC Code:
12352200
PubChem Substance ID:
86280479
NACRES:
NA.77

assay

≥94% (HPLC)

Quality Level

100

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

tan

solubility

DMSO: 50 mg/mL

storage temp.

2-8°C

SMILES string

C1CCC(=NNC2=NC(=CS2)C3=CC=C(C=C3)C#N)C1.Br

General description

A cell-permeable, potent, and stable analog of CPTH2 (Cat. No. 382111) that restores nuclear shape and chromatin compactin in AG11498 and AG06297 progeric fibroblasts from Hutchinson-Gilford progeria syndrome (HGPS) patients and in lamin A/C-depleted U2OS cells by inhibiting the activity of N-acetyltransferase 10 (NAT10; 10-50 µM). However, it does not affect non-laminopathic Werner syndrome cells. Improves DNA replication and enhances cell proliferation capacity. Also shown to prevent farnesyltransferase inhibitor-induced nuclear shape defects in normal fibroblasts and in U2OS cells and improves nuclear morphology in siLMNA (lamin A/C depletion by small interfering RNA transfection) treated cells. Does not affect Golgi apparatus integrity or tubulin polymer assembly and its effects are independent of mitosis.
A cell-permeable, potent, and stable analog of CPTH2 (Cat. No. 382111) that restores nuclear shape and chromatin compactin in AG11498 and AG06297 progeric fibroblasts from Hutchinson-Gilford progeria syndrome (HGPS) patients and in lamin A/C-depleted U2OS cells by inhibiting the activity of N-acetyltransferase 10 (NAT10; 10-50 µM). However, it does not affect non-laminopathic Werner syndrome cells. Improves DNA replication and enhances cell proliferation capacity. Also shown to prevent farnesyltransferase inhibitor-induced nuclear shape defects in normal fibroblasts and in U2OS cells and improves nuclear morphology in siLMNA (lamin A/C depletion by small interfering RNA transfection) treated cells. Does not affect Golgi apparatus integrity or tubulin polymer assembly and its effects are independent of mitosis.

Please note that the molecular weight for this compound is batch-specific due to variable water content.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
NAT10
Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Larrieu, D., et al. 2014. Science344, 527.

Legal Information

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Delphine Larrieu et al.
Science (New York, N.Y.), 344(6183), 527-532 (2014-05-03)
Down-regulation and mutations of the nuclear-architecture proteins lamin A and C cause misshapen nuclei and altered chromatin organization associated with cancer and laminopathies, including the premature-aging disease Hutchinson-Gilford progeria syndrome (HGPS). Here, we identified the small molecule "Remodelin" that improved

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