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T7580

Sigma-Aldrich

TN-16

≥98% (HPLC)

Synonym(s):

3-[1-(Phenylamino)ethylidene]-5-(phenylmethyl)-2,4-pyrrolidinedione, NSC 239274

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About This Item

Empirical Formula (Hill Notation):
C19H18N2O2
CAS Number:
33016-12-5
Molecular Weight:
306.36
UNSPSC Code:
51111800
PubChem Substance ID:
329826871
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥17 mg/mL

storage temp.

2-8°C

SMILES string

C\C(Nc1ccccc1)=C2\C(=O)NC(Cc3ccccc3)C2=O

InChI

1S/C19H18N2O2/c1-13(20-15-10-6-3-7-11-15)17-18(22)16(21-19(17)23)12-14-8-4-2-5-9-14/h2-11,16,20H,12H2,1H3,(H,21,23)/b17-13-

InChI key

KWSXUGYAGMSUTN-LGMDPLHJSA-N

Application

TN-16 has been used as a microtubule disrupting agent to study its effect on autophagic process in human and mouse mammary carcinoma cell lines .

Biochem/physiol Actions

3-(l-anilinoethylidene)-5-benzylpyrrolidine-2,4-dione (TN-16), a tenuazonic acid derivative, is a synthetic antitumor agent which arrests mitosis of tumor cells at metaphase. It is a colchicine site binding agent and a powerful autophagy flux inhibitor that could be used as a conventional autophagy inhibitor with anti-cancer potential in pre-clinical trials.
Inhibitor of microtubule assembly
TN-16 is a synthetic compound that blocks the assembly, and promotes the dissociation of microtubules. It can prevent the b-TrCP-mediated degradation of the transcription factor Gli2, leading to the up-regulation of BMP-2 and supporting a role for microtubule formation in the regulation of bone formation.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H317,H400

Hazard Classifications

Aquatic Acute 1 - Skin Sens. 1

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Nobuaki Shono et al.
Journal of cell science, 128(24), 4572-4587 (2015-11-04)
Although it is generally accepted that chromatin containing the histone H3 variant CENP-A is an epigenetic mark maintaining centromere identity, the pathways leading to the formation and maintenance of centromere chromatin remain unclear. We previously generated human artificial chromosomes (HACs)
T Arai
FEBS letters, 155(2), 273-276 (1983-05-08)
An antitumor drug, 3-(1-anilinoethylidene)-5-benzylpyrrolidine-2,4-dione (TN-16) inhibited the assembly of porcine brain microtubules in vitro. The assembly induced by taxol was also suppressed by the drug. However, the latter required much higher concentration of TN-16 than the former. Binding studies by
M Nakamura et al.
Cancer letters, 69(2), 85-91 (1993-04-30)
A study was conducted on the effect of vinblastine (VBL), an anti-mitotic drug that is commonly employed in the treatment of human renal cell carcinoma. When VBL was added to serum-free cultures of the ACHN and NT cell lines (both
Yuko Kojima et al.
Biochemical and biophysical research communications, 296(2), 328-336 (2002-08-07)
Fas ligand (FasL) has been implicated in cytotoxic T lymphocyte (CTL)- and natural killer (NK) cell-mediated cytotoxicity. In the present study, we investigated the localization of FasL in murine CTL and NK cells. Immunocytochemical staining showed that FasL was stored
Mohammad Hasanain et al.
Cell proliferation, 53(4), e12749-e12749 (2020-03-14)
Given that autophagy inhibition is a feasible way to enhance sensitivity of cancer cells towards chemotherapeutic agents, identifying potent autophagy inhibitor has obvious clinical relevance. Here, we investigated ability of TN-16, a microtubule disrupting agent, on modulation of autophagic flux

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