MedKoo Cat#: 203055 | Name: Tubacin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Tubacin
Tubacin
CAS#537049-40-4

Theoretical Analysis

MedKoo Cat#: 203055

Name: Tubacin

CAS#: 537049-40-4

Chemical Formula: C41H43N3O7S

Exact Mass: 721.2822

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
1mg USD 285.00 2 weeks
5mg USD 650.00 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
More Info
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.      
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
1: Yimiti M, Fei X, Yang H, Yang X, Li S, Tuoheniyazi H, Liu D, Ma J, Xie J, Zheng J, Song Z, Li Q, Xu D, Zhao Y, Gu Z. HDAC6 inhibitor promotes reactive oxygen species-meditated clearance of Staphylococcus aureus in macrophage. Clin Exp Pharmacol Physiol. 2024 Jun;51(6):e13866. doi: 10.1111/1440-1681.13866. PMID: 38719209. 2: Mozzicato AM, Bastrup JA, Sanchez-Alonso JL, van der Horst J, Gorelik J, Hägglund P, Jepps TA. Mesenteric artery smooth muscle cells from hypertensive rats have increased microtubule acetylation. Biochem J. 2024 Mar 6;481(5):387-403. doi: 10.1042/BCJ20230420. PMID: 38373073. 3: Uba AI, Hryb M, Singh M, Bui-Linh C, Tran A, Atienza J, Misbah S, Mou X, Wu C. Discovery of novel inhibitors of histone deacetylase 6: Structure-based virtual screening, molecular dynamics simulation, enzyme inhibition and cell viability assays. Life Sci. 2024 Feb 1;338:122395. doi: 10.1016/j.lfs.2023.122395. Epub 2024 Jan 3. PMID: 38181853. 4: Liu L, Liu X, Chen Y, Kong M, Zhang J, Jiang M, Zhou H, Yang J, Chen X, Zhang Z, Wu C, Jiang X, Zhang J. Paxillin/HDAC6 regulates microtubule acetylation to promote directional migration of keratinocytes driven by electric fields. Biochim Biophys Acta Mol Cell Res. 2024 Feb;1871(2):119628. doi: 10.1016/j.bbamcr.2023.119628. Epub 2023 Nov 10. PMID: 37949303. 5: Li XY, Yu JT, Dong YH, Shen XY, Hou R, Xie MM, Wei J, Hu XW, Dong ZH, Shan RR, Jin J, Shao W, Meng XM. Protein acetylation and related potential therapeutic strategies in kidney disease. Pharmacol Res. 2023 Nov;197:106950. doi: 10.1016/j.phrs.2023.106950. Epub 2023 Oct 17. PMID: 37820854. 6: Calogero AM, Basellini MJ, Isilgan HB, Longhena F, Bellucci A, Mazzetti S, Rolando C, Pezzoli G, Cappelletti G. Acetylated α-Tubulin and α-Synuclein: Physiological Interplay and Contribution to α-Synuclein Oligomerization. Int J Mol Sci. 2023 Jul 31;24(15):12287. doi: 10.3390/ijms241512287. PMID: 37569662; PMCID: PMC10418364. 7: López-Guajardo A, Zafar A, Al Hennawi K, Rossi V, Alrwaili A, Medcalf JD, Dunning M, Nordgren N, Pettersson T, Estabrook ID, Hawkins RJ, Gad AKB. Regulation of cellular contractile force, shape and migration of fibroblasts by oncogenes and Histone deacetylase 6. Front Mol Biosci. 2023 Jul 20;10:1197814. doi: 10.3389/fmolb.2023.1197814. PMID: 37564130; PMCID: PMC10411354. 8: Peng C, Gong X, Hu Z, Chen C, Jiang Z. Selective HDAC6 inhibitor TubA offers neuroprotection after intracerebral hemorrhage via inhibiting neuronal apoptosis. PeerJ. 2023 Apr 28;11:e15293. doi: 10.7717/peerj.15293. PMID: 37138816; PMCID: PMC10150719. 9: Li Z, Duan P, Qiu R, Fang L, Fang P, Xiao S. HDAC6 Degrades nsp8 of Porcine Deltacoronavirus through Deacetylation and Ubiquitination to Inhibit Viral Replication. J Virol. 2023 May 31;97(5):e0037523. doi: 10.1128/jvi.00375-23. Epub 2023 May 3. PMID: 37133375; PMCID: PMC10231189. 10: Xu W, Yan P, Zhou Z, Yao J, Pan H, Jiang L, Bo Z, Ni B, Sun M, Gao S, Huan C. HDAC6 Triggers the ATM-Dependent DNA Damage Response To Promote PRV Replication. Microbiol Spectr. 2023 Mar 23;11(2):e0213222. doi: 10.1128/spectrum.02132-22. Epub ahead of print. PMID: 36951571; PMCID: PMC10101138. 11: Tsai YC, Wang TY, Hsu CL, Lin WC, Chen JY, Li JH, Pu YS, Cheng AL, Cheng JC, Su SF. Selective inhibition of HDAC6 promotes bladder cancer radiosensitization and mitigates the radiation-induced CXCL1 signalling. Br J Cancer. 2023 May;128(9):1753-1764. doi: 10.1038/s41416-023-02195-0. Epub 2023 Feb 21. PMID: 36810912; PMCID: PMC10133394. 12: Miyazawa B, Trivedi A, Vivona L, Lin M, Potter D, Nair A, Barry M, Cap AP, Pati S. Histone deacetylase-6 modulates the effects of 4°C platelets on vascular endothelial permeability. Blood Adv. 2023 Apr 11;7(7):1241-1257. doi: 10.1182/bloodadvances.2022007409. PMID: 36375044; PMCID: PMC10090218. 13: Renguet E, De Loof M, Fourny N, Ginion A, Bouzin C, Poüs C, Horman S, Beauloye C, Bultot L, Bertrand L. α-Tubulin acetylation on lysine 40 controls cardiac glucose uptake. Am J Physiol Heart Circ Physiol. 2022 Jun 1;322(6):H1032-H1043. doi: 10.1152/ajpheart.00664.2021. Epub 2022 Apr 29. PMID: 35486479. 14: Octave M, Pirotton L, Ginion A, Robaux V, Lepropre S, Ambroise J, Bouzin C, Guigas B, Giera M, Foretz M, Bertrand L, Beauloye C, Horman S. Acetyl-CoA Carboxylase Inhibitor CP640.186 Increases Tubulin Acetylation and Impairs Thrombin-Induced Platelet Aggregation. Int J Mol Sci. 2021 Dec 4;22(23):13129. doi: 10.3390/ijms222313129. PMID: 34884932; PMCID: PMC8658010. 15: Nomura Y, Nakano M, Woo Sung H, Han M, Pandey D. Inhibition of HDAC6 Activity Protects Against Endothelial Dysfunction and Atherogenesis in vivo: A Role for HDAC6 Neddylation. Front Physiol. 2021 Jun 17;12:675724. doi: 10.3389/fphys.2021.675724. PMID: 34220539; PMCID: PMC8245780. 16: Alothaim T, Charbonneau M, Tang X. HDAC6 inhibitors sensitize non- mesenchymal triple-negative breast cancer cells to cysteine deprivation. Sci Rep. 2021 May 26;11(1):10956. doi: 10.1038/s41598-021-90527-6. PMID: 34040090; PMCID: PMC8155140. 17: Wu H, Wang Z, Liu S, Meng H, Liu S, Fu S. Sub-toxic levels of cobalt ions impair chondrocyte mechanostranduction via HDAC6-dependent primary cilia shortening. Biochem Biophys Res Commun. 2021 Mar 12;544:38-43. doi: 10.1016/j.bbrc.2021.01.041. Epub 2021 Jan 28. Erratum in: Biochem Biophys Res Commun. 2021 May 28;555:213. doi: 10.1016/j.bbrc.2021.03.157. PMID: 33516880. 18: Kotwal A, Suran S, Amere Subbarao S. Hsp90 chaperone facilitates E2F1/2-dependent gene transcription in human breast cancer cells. Eur J Cell Biol. 2021 Jan;100(1):151148. doi: 10.1016/j.ejcb.2020.151148. Epub 2020 Dec 29. Erratum in: Eur J Cell Biol. 2021 Apr;100(3):151157. doi: 10.1016/j.ejcb.2021.151157. PMID: 33388604. 19: Wang X, Wang L, Sun Y, Chen B, Xiong L, Chen J, Huang M, Wu J, Tan X, Zheng Y, Huang S, Liu Y. MiR-22-3p inhibits fibrotic cataract through inactivation of HDAC6 and increase of α-tubulin acetylation. Cell Prolif. 2020 Nov;53(11):e12911. doi: 10.1111/cpr.12911. Epub 2020 Sep 28. PMID: 32985730; PMCID: PMC7653254. 20: Liang T, Qi C, Lai Y, Xie J, Wang H, Zhang L, Lin T, Jv M, Li J, Wang Y, Zhang Y, Chen Z, Qiu X, Li R, Li Z, Ye Z, Liu S, Liang X, Shi W, Wang W. HDAC6-mediated α-tubulin deacetylation suppresses autophagy and enhances motility of podocytes in diabetic nephropathy. J Cell Mol Med. 2020 Oct;24(19):11558-11572. doi: 10.1111/jcmm.15772. Epub 2020 Sep 4. PMID: 32885602; PMCID: PMC7576268.