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SML0065

Sigma-Aldrich

Tubacin

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C41H43N3O7S
Numéro CAS:
537049-40-4
Poids moléculaire :
721.86
Numéro MDL:
MFCD18452824
Code UNSPSC :
12352200
ID de substance PubChem :
329825129
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to tan

Solubilité

DMSO: ≥10 mg/mL

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

BHUZLJOUHMBZQY-YXQOSMAKSA-N

Application

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
Vijay G Ramakrishnan et al.
Haematologica, 104(10), 2061-2074 (2019-03-09)
Despite recent advances in the treatment of multiple myeloma, patients with this disease still inevitably relapse and become refractory to existing therapies. Mutations in K-RAS, N-RAS and B-RAF are common in multiple myeloma, affecting 50% of patients at diagnosis and
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