Tubacin
Tubacin (CAS 537049-40-4) is a selective, reversible, and cell-permeable inhibitor of histone deacetylase 6 (HDAC6). HDAC6, a zinc-dependent enzyme, regulates protein deacetylation, including that of α-tubulin, thereby influencing various cellular functions such as microtubule dynamics and protein degradation. Tubacin shows potent inhibitory activity against HDAC6 (IC50 = 4 nM), with significant selectivity compared to HDAC1 (~350-fold). In A549 cells, Tubacin treatment increases α-tubulin acetylation levels (EC50 = 2.5 μM). Studies indicate its utility in oncology research, evidenced by antiproliferative and pro-apoptotic effects in acute lymphoblastic leukemia (ALL) cells, as well as potential implications in treating models of Alzheimer's disease.
- 1. Joseph Boyle, Derick Chiappo, et al. "Aminocoumarin-based heme oxygenase activity fluorescence probe reveals novel aspects of HO-1 regulation." Research Square. 22 Nov, 2023.
- 2. Tang Y, Yu W. "SIRT1 and p300/CBP regulate the reversible acetylation of serine-threonine kinase NDR2." Biochem Biophys Res Commun. 2019 Aug 16. pii: S0006-291X(19)31586-4. PMID:31427083
- 3. Hari Prasad, Rajini Rao. "The Amyloid Clearance Defect in ApoE4 Astrocytes is Corrected by Epigenetic Restoration of NHE6." bioRxiv. 2018.January. 4
- 4. Sedgwick A, Olivia Balmert M, et al. "The formation of giant plasma membrane vesicles enable new insights into the regulation of cholesterol efflux." Exp Cell Res. 2018 Apr 15;365(2):194-207. PMID:29522754
- 5. Yan Y, Wang H, et al. "HDAC6 Suppresses Age-Dependent Ectopic Fat Accumulation by Maintaining the Proteostasis of PLIN2 in Drosophila." Dev Cell. 2017 Oct 9;43(1):99-111.e5. PMID:28966044
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 721.86 |
| Cas No. | 537049-40-4 |
| Formula | C41H43N3O7S |
| Solubility | insoluble in EtOH; insoluble in H2O; ≥7.19 mg/mL in DMSO |
| Chemical Name | N-[4-[(2R,4R,6S)-4-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanylmethyl]-6-[4-(hydroxymethyl)phenyl]-1,3-dioxan-2-yl]phenyl]-N'-hydroxyoctanediamide |
| SDF | Download SDF |
| Canonical SMILES | C1C(OC(OC1C2=CC=C(C=C2)CO)C3=CC=C(C=C3)NC(=O)CCCCCCC(=O)NO)CSC4=NC(=C(O4)C5=CC=CC=C5)C6=CC=CC=C6 |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment [1,2]: | |
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Cell lines |
Human A549 lung carcinoma cells, Mouse NIH 3T3 wild-type (Neo), HDAC6, HDAC6 double-mutant, and HDAC6-overexpressing cells, Acute lymphoblastic leukemia (ALL) cells |
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Preparation method |
Limited soluble in DMSO. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
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Reacting condition |
2 μM, 4.5 h |
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Applications |
In cultured cells, tubacin (10 μM) induced up to a 3-fold increase in the relative α-tubulin-acetylation level, with a half-maximum effective concentration (EC50) of 2.5 μM. Tubacin (2 μM) inhibited the migration of both wild-type and HDAC6-overexpressing cells. Tubacin treatment increased the colocalization of HDAC6 along acetylated microtubules in interphase cells. Treatment with tubacin led to the induction of apoptotic pathways in both pre-B and T cell ALL cells. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Haggarty S J, Koeller K M, Wong J C, et al. Domain-selective small-molecule inhibitor of histone deacetylase 6 (HDAC6)-mediated tubulin deacetylation[J]. Proceedings of the National Academy of Sciences, 2003, 100(8): 4389-4394. [2]. Aldana-Masangkay G I, Rodriguez-Gonzalez A, Lin T, et al. Tubacin suppresses proliferation and induces apoptosis of acute lymphoblastic leukemia cells[J]. Leukemia & lymphoma, 2011, 52(8): 1544-1555. |
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| Description | Tubacin is a highly potent and selective, reversible, cell-permeable inhibitor of HDAC6 with an IC50 value of 4 nM. | |||||
| Targets | HDAC6 | |||||
| IC50 | 4 nM | |||||
Quality Control & MSDS
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Chemical structure
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