Tubastatin A
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MedKoo CAT#: 403550

CAS#: 1252003-15-8 (free base)

Description: Tubastatin A is a potent and selective HDAC6 inhibitor. Tubastatin A demonstrates 1093-fold selectivity over HDAC1 (IC50 values of 15 nM for HDAC6 vs 16.4 µM for HDAC1). Tubastatin A was substantially more selective than the known HDAC6 inhibitor Tubacin at all isozymes except HDAC8. Tubastatin A is a potent HDAC6 inhibitor with an IC50 value of 15 nM. Comparatively, it demonstrates over 1,000-fold selectivity against all other HDAC isoforms (IC50 >16 μM), excluding HDAC8 (IC50= 0.9 μM). Tubastatin A induces α-tubulin hyperacetylation at 2.5 μM in primary cortical neuron cultures. In a model of oxidative stress induced by glutathione depletion, tubastatin A displays dose-dependent neuronal protection of primary cortical neuron cultures at 5-10 μM.


Price and Availability

Size
Price

10mg
USD 150
500mg
USD 1450
Size
Price

25mg
USD 250
1g
USD 2250
Size
Price

100mg
USD 650
2g
USD 3950

Tubastatin A, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 500mg may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 403550
Name: Tubastatin A
CAS#: 1252003-15-8 (free base)
Chemical Formula: C20H21N3O2
Exact Mass: 335.16338
Molecular Weight: 335.4
Elemental Analysis: C, 71.62; H, 6.31; N, 12.53; O, 9.54


Related CAS #: 1310693-92-5 (HCl)   1252003-15-8 (free base)    

Synonym: Tubastatin A

IUPAC/Chemical Name: N-hydroxy-4-((2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzamide

InChi Key: GOVYBPLHWIEHEJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H21N3O2/c1-22-11-10-19-17(13-22)16-4-2-3-5-18(16)23(19)12-14-6-8-15(9-7-14)20(24)21-25/h2-9,25H,10-13H2,1H3,(H,21,24)

SMILES Code: O=C(NO)C1=CC=C(CN2C3=C(CN(C)CC3)C4=C2C=CC=C4)C=C1


Technical Data

Appearance:
white solid powder

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

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).

Harmonized System Code:
293490


Additional Information

   
 
 


References

1: Kozlov MV, Kleymenova AA, Konduktorov KA, Malikova AZ, Kochetkov SN. Selective inhibitor of histone deacetylase 6 (tubastatin A) suppresses proliferation of hepatitis C virus replicon in culture of human hepatocytes. Biochemistry (Mosc). 2014 Jul;79(7):637-42. doi: 10.1134/S0006297914070050. PubMed PMID: 25108326.

2: Zhang Y, Liu CM, Cao XC, Zang Y, Zhou YB, Li J. Involvement of transcription factor XBP1s in the resistance of HDAC6 inhibitor Tubastatin A to superoxidation via acetylation-mediated proteasomal degradation. Biochem Biophys Res Commun. 2014 Jul 18;450(1):433-9. doi: 10.1016/j.bbrc.2014.05.134. Epub 2014 Jun 6. PubMed PMID: 24909686.

3: Zhang L, Liu C, Wu J, Tao JJ, Sui XL, Yao ZG, Xu YF, Huang L, Zhu H, Sheng SL, Qin C. Tubastatin A/ACY-1215 improves cognition in Alzheimer's disease transgenic mice. J Alzheimers Dis. 2014;41(4):1193-205. doi: 10.3233/JAD-140066. PubMed PMID: 24844691.

4: Kozlov MV, Kleĭmenova AA, Konduktorov KA, Kochetkov SN. [New synthesis of highly selective inhibitor of histone deacetylase 6--N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3b]indol-5-ylmethyl)benzamid e--Tubastatin A]. Bioorg Khim. 2013 Jan-Feb;39(1):117-20. Russian. PubMed PMID: 23844513.

5: Vishwakarma S, Iyer LR, Muley M, Singh PK, Shastry A, Saxena A, Kulathingal J, Vijaykanth G, Raghul J, Rajesh N, Rathinasamy S, Kachhadia V, Kilambi N, Rajgopal S, Balasubramanian G, Narayanan S. Tubastatin, a selective histone deacetylase 6 inhibitor shows anti-inflammatory and anti-rheumatic effects. Int Immunopharmacol. 2013 May;16(1):72-8. doi: 10.1016/j.intimp.2013.03.016. Epub 2013 Mar 27. PubMed PMID: 23541634.

6: De Vreese R, Verhaeghe T, Desmet T, D'hooghe M. Potent and selective HDAC6 inhibitory activity of N-(4-hydroxycarbamoylbenzyl)-1,2,4,9-tetrahydro-3-thia-9-azafluorenes as novel sulfur analogues of Tubastatin A. Chem Commun (Camb). 2013 May 8;49(36):3775-7. doi: 10.1039/c3cc41422a. Epub 2013 Mar 28. PubMed PMID: 23538448.

7: Butler KV, Kalin J, Brochier C, Vistoli G, Langley B, Kozikowski AP. Rational design and simple chemistry yield a superior, neuroprotective HDAC6 inhibitor, tubastatin A. J Am Chem Soc. 2010 Aug 11;132(31):10842-6. doi: 10.1021/ja102758v. PubMed PMID: 20614936; PubMed Central PMCID: PMC2916045.