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SML0065

Sigma-Aldrich

Tubacin

≥98% (HPLC)

Synonym(s):

N1-[4-[(2R,4R,6S)-4-[[(4,5-diphenyl-2-oxazolyl)thio]methyl]-6-[4-(hydroxymethyl)phenyl]-1,3-dioxan-2-yl]phenyl]-N8-hydroxy-octanediamide

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About This Item

Empirical Formula (Hill Notation):
C41H43N3O7S
CAS Number:
537049-40-4
Molecular Weight:
721.86
MDL number:
MFCD18452824
UNSPSC Code:
12352200
PubChem Substance ID:
329825129
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to tan

solubility

DMSO: ≥10 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

OCC1=CC=C(C=C1)[C@@H]2C[C@H](CSC3=NC(C4=CC=CC=C4)=C(C5=CC=CC=C5)O3)O[C@H](C6=CC=C(NC(CCCCCCC(NO)=O)=O)C=C6)O2

InChI

1S/C41H43N3O7S/c45-26-28-17-19-29(20-18-28)35-25-34(27-52-41-43-38(30-11-5-3-6-12-30)39(51-41)31-13-7-4-8-14-31)49-40(50-35)32-21-23-33(24-22-32)42-36(46)15-9-1-2-10-16-37(47)44-48/h3-8,11-14,17-24,34-35,40,45,48H,1-2,9-10,15-16,25-27H2,(H,42,46)(H,44,47)/t34-,35+,40+/m1/s1

InChI key

BHUZLJOUHMBZQY-YXQOSMAKSA-N

Application

Tubacin was used to study the role of HDAC6 in migration and invasion of bladder cancer cells.

Biochem/physiol Actions

Tubacin is a selective inhibitor of histone deacetylase 6 (HDAC6), a predominantly cytoplasmic class II histone deacetylase that is involved in many cellular processes, including degradation of misfolded proteins, cell migration, and cell-cell interaction. Tubacin selectively inhibit HDAC6-mediated alpha -tubulin deacetylation.
Tubacin triggers the release of reactive oxygen species and mediates caspase-3-independent apoptosis of Epstein-Barr virus (EBV)-positive Burkitt lymphoma cells. It suppresses the proliferation of acute lymphoblastic leukemia (ALL) cells and enhances the effect of chemotherapy to treat ALL cells. Tubacin prevents the epileptic activity and neuronal migration defects caused due to lowered expression of Srpx2 in rats.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class Code

11 - Combustible Solids

WGK

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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Harald Witte et al.
The Journal of cell biology, 180(3), 619-632 (2008-02-13)
Axon formation is the initial step in establishing neuronal polarity. We examine here the role of microtubule dynamics in neuronal polarization using hippocampal neurons in culture. We see increased microtubule stability along the shaft in a single neurite before axon
Hui Tao et al.
Cardiology, 133(1), 18-26 (2015-09-25)
Cardiac fibrosis is characterized by net accumulation of extracellular matrix proteins in the cardiac interstitium, and contributes to both systolic and diastolic dysfunction in many cardiac pathophysiologic conditions. HDAC6 is a transcriptional regulator of the histone deacetylase family, subfamily 2.
Junichi Kawada et al.
The Journal of biological chemistry, 284(25), 17102-17109 (2009-04-24)
Tubacin is a small molecule inhibitor of histone deacetylase 6 and blocks aggresome activity. We found that Epstein-Barr virus (EBV)-positive Burkitt lymphoma (BL) cells were generally killed by lower doses of tubacin than EBV-transformed lymphoblastoid cells (LCLs) or EBV-negative BL
Laura Melchionda et al.
Orphanet journal of rare diseases, 8, 66-66 (2013-05-03)
We studied a family including two half-siblings, sharing the same mother, affected by slowly progressive, adult-onset neurological syndromes. In spite of the diversity of the clinical features, characterized by a mild movement disorder with cognitive impairment in the elder patient
Manal Salmi et al.
Brain : a journal of neurology, 136(Pt 8), 2457-2473 (2013-07-09)
Altered development of the human cerebral cortex can cause severe malformations with often intractable focal epileptic seizures and may participate in common pathologies, notably epilepsy. This raises important conceptual and therapeutic issues. Two missense mutations in the sushi repeat-containing protein
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