Tubacin
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MedKoo CAT#: 203055

CAS#: 537049-40-4

Description: Tubacin is a highly potent and selective, reversible, cell-permeable HDAC6 inhibitor with an IC50 of 4 nM. The IC50 for other HDACs is 1000-fold higher, making tubacin both more selective and more potent than Tubastatin A, which also inhibits HDAC8. Tubacin inhibits alpha-tubulin deacetylation in mammalian cells. Unlike trichostatin A (TSA), which is a broad spectrum HDAC inhibitor, tubacin is specific for the tubulin deacetylase activity of HDAC6.


Chemical Structure

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Tubacin
CAS# 537049-40-4

Theoretical Analysis

MedKoo Cat#: 203055
Name: Tubacin
CAS#: 537049-40-4
Chemical Formula: C41H43N3O7S
Exact Mass: 721.28217
Molecular Weight: 721.86
Elemental Analysis: C, 68.22; H, 6.00; N, 5.82; O, 15.51; S, 4.44

Price and Availability

Size Price Availability Quantity
1.0mg USD 250.0 2 weeks
5.0mg USD 550.0 2 weeks
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Synonym: Tubacin

IUPAC/Chemical Name: N1-(4-((2R,4R,6S)-4-(((4,5-diphenyloxazol-2-yl)thio)methyl)-6-(4-(hydroxymethyl)phenyl)-1,3-dioxan-2-yl)phenyl)-N8-hydroxyoctanediamide

InChi Key: BHUZLJOUHMBZQY-YXQOSMAKSA-N

InChi Code: 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

SMILES Code: O=C(NC1=CC=C([C@@H]2O[C@H](C3=CC=C(CO)C=C3)C[C@H](CSC4=NC(C5=CC=CC=C5)=C(C6=CC=CC=C6)O4)O2)C=C1)CCCCCCC(NO)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 721.86 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Siow D, Wattenberg B. The histone deacetylase-6 inhibitor tubacin directly inhibits de novo sphingolipid biosynthesis as an off-target effect. Biochem Biophys Res Commun. 2014 Jul 4;449(3):268-71. doi: 10.1016/j.bbrc.2014.05.016. Epub 2014 May 14. PubMed PMID: 24835950.

2: Salmi M, Bruneau N, Cillario J, Lozovaya N, Massacrier A, Buhler E, Cloarec R, Tsintsadze T, Watrin F, Tsintsadze V, Zimmer C, Villard C, Lafitte D, Cardoso C, Bao L, Lesca G, Rudolf G, Muscatelli F, Pauly V, Khalilov I, Durbec P, Ben-Ari Y, Burnashev N, Represa A, Szepetowski P. Tubacin prevents neuronal migration defects and epileptic activity caused by rat Srpx2 silencing in utero. Brain. 2013 Aug;136(Pt 8):2457-73. doi: 10.1093/brain/awt161. Epub 2013 Jul 5. PubMed PMID: 23831613.

3: Aldana-Masangkay GI, Rodriguez-Gonzalez A, Lin T, Ikeda AK, Hsieh YT, Kim YM, Lomenick B, Okemoto K, Landaw EM, Wang D, Mazitschek R, Bradner JE, Sakamoto KM. Tubacin suppresses proliferation and induces apoptosis of acute lymphoblastic leukemia cells. Leuk Lymphoma. 2011 Aug;52(8):1544-55. doi: 10.3109/10428194.2011.570821. Epub 2011 Jun 23. PubMed PMID: 21699378; PubMed Central PMCID: PMC4113006.

4: Kawada J, Zou P, Mazitschek R, Bradner JE, Cohen JI. Tubacin kills Epstein-Barr virus (EBV)-Burkitt lymphoma cells by inducing reactive oxygen species and EBV lymphoblastoid cells by inducing apoptosis. J Biol Chem. 2009 Jun 19;284(25):17102-9. doi: 10.1074/jbc.M809090200. Epub 2009 Apr 22. PubMed PMID: 19386607; PubMed Central PMCID: PMC2719348.

Tubacin

1.0mg / USD 250.0


Additional Information

Tubacin was originally discovered by scientists at the Broad Institute after performing a cell-based screen of a library of over 7000 small molecules. Tubacin is a highly potent, selective, reversible, cell-permeable HDAC6 inhibitor with an IC50 of 4 nM. The IC50 for other HDACs is 1000-fold higher, making tubacin both more selective and more potent than Tubastatin A.
 
According to Aldana-Masangkay et al's recent publication ( Leuk Lymphoma. 2011 Aug;52(8):1544-55. )  tubacin showed a higher antiproliferative effect in acute lymphoblastic leukemia (ALL) cells than in normal hematopoietic cells. Treatment with tubacin led to the induction of apoptotic pathways in both pre-B and T cell ALL cells at a 50% inhibitory concentration (IC(50)) of low micromolar concentrations. Acetylation of α-tubulin increases within the first 30 min following treatment of ALL cells with tubacin . It was also observed an accumulation of polyubiquitinated proteins and poly(ADP-ribose) polymerase (PARP) cleavage. Furthermore, the signaling pathways activated by tubacin appear to be distinct from those observed in multiple myeloma. The results suggest that targeting HDAC6 alone or in combination with chemotherapy could provide a novel approach to treat ALL.