Details
Stereochemistry | RACEMIC |
Molecular Formula | C41H43N3O7S |
Molecular Weight | 721.861 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OCC1=CC=C(C=C1)[C@@H]2C[C@H](CSC3=NC(=C(O3)C4=CC=CC=C4)C5=CC=CC=C5)O[C@@H](O2)C6=CC=C(NC(=O)CCCCCCC(=O)NO)C=C6
InChI
InChIKey=BHUZLJOUHMBZQY-YXQOSMAKSA-N
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
Molecular Formula | C41H43N3O7S |
Molecular Weight | 721.861 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20614936 | https://www.ncbi.nlm.nih.gov/pubmed/18472289Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15937109
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20614936 | https://www.ncbi.nlm.nih.gov/pubmed/18472289
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15937109
Tubacin is a highly potent and selective, reversible, cell-permeable inhibitor of HDAC6 with an IC50 value of 4 nM. Tubacin inhibits α- tubulin deacetylation in mammalian cells. Tubacin is specific for the tubulin deacetylase activity of HDAC6. The effects of tubacin has been studied in hematologic malignancies, such as multiple myeloma and leukemia cell lines. Overexpression of HDAC6 in primary lymphocytes and T cell lines increase cell migration in response to cytokines. Knockdown of HDAC6 in T cells decreased chemotactic mobility independent of its enzymatic activity. Furthermore, treatment of multiple myeloma cells with tubacin resulted in decreased cell growth at an IC50 of 2–5uM. In terms of toxicity to normal bone marrow and blood cells, treatment of peripheral blood mononuclear cells (PBMC) and bone marrow progenitor cells (BMPC) with tubacin (5uM) for 12 hours showed that constitutive expression of HDAC6 is higher in BMPCs than PBMCs. Furthermore, acetylation of α-tubulin was markedly enhanced by tubacin in BMPCs but not in PBMCs. Bortezomib and tubacin together induced synergistic antitumor activity in multiple myeloma cells and primary bone marrow plasma cells. Published data therefore provide support for combined therapy in clinical trials for patients with multiple myeloma.
CNS Activity
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Domain-selective small-molecule inhibitor of histone deacetylase 6 (HDAC6)-mediated tubulin deacetylation. | 2003 Apr 15 |
|
Ubiquitin proteasome system stress underlies synergistic killing of ovarian cancer cells by bortezomib and a novel HDAC6 inhibitor. | 2008 Nov 15 |
|
Grouping of histone deacetylase inhibitors and other toxicants disturbing neural crest migration by transcriptional profiling. | 2015 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21699378
Mice: mice were treated for 4 weeks intraperitoneally with
50 mg/kg/day tubacin
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21699378
Tubacin inhibited the growth of ALL cells in a dose-dependent manner, with 50% inhibitory
concentrations (IC50) ranging from 1.2 to 2 uM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:31:17 GMT 2023
by
admin
on
Sat Dec 16 10:31:17 GMT 2023
|
Record UNII |
02C2G1D30D
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
537049-40-4
Created by
admin on Sat Dec 16 10:31:17 GMT 2023 , Edited by admin on Sat Dec 16 10:31:17 GMT 2023
|
PRIMARY | |||
|
02C2G1D30D
Created by
admin on Sat Dec 16 10:31:17 GMT 2023 , Edited by admin on Sat Dec 16 10:31:17 GMT 2023
|
PRIMARY | |||
|
6675804
Created by
admin on Sat Dec 16 10:31:17 GMT 2023 , Edited by admin on Sat Dec 16 10:31:17 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |