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Tubulysin B

Names

[ CAS No. ]:
205304-87-6

[ Name ]:
Tubulysin B

[Synonym ]:
(2S,4R)-4-[({2-[(1R,3R)-1-Acetoxy-3-{[(butyryloxy)methyl](N-{[(2R)-1-methyl-2-piperidinyl]carbonyl}-L-isoleucyl)amino}-4-methylpentyl]-1,3-thiazol-4-yl}carbonyl)amino]-5-(4-hydroxyphenyl)-2-methylpentanoic acid
Tubulysin B
Pentanoic acid, 4-[[[2-[(1R,3R)-1-(acetyloxy)-4-methyl-3-[[(2S,3S)-3-methyl-2-[[[(2R)-1-methyl-2-piperidinyl]carbonyl]amino]-1-oxopentyl][(1-oxobutoxy)methyl]amino]pentyl]-4-thiazolyl]carbonyl]amino]-5-(4-hydroxyphenyl)-2-methyl-, (2S,4R)-

Biological Activity

[Description]:

Tubulysin B is a highly cytotoxic peptide and potent microtubule destabilizing agents isolated from the myxobacteria Archangium geophyra and Angiococcus disciformis. Tubulysin B has IC50 values in the picomolar range against many cancer cell lines, including those with multidrug resistant properties[1].Tubulysin B is a cytotoxic activity tubulysin which inhibits tubulin polymerization and leads to cell cycle arrest and apoptosis[2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin
Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

[In Vitro]

Tubulysin B has IC50s of 0.6 and 0.9 nM against KB and A549 tumors cell lines, respectively.

[References]

[1]. Leamon CP, et al. Prostate-Specific Membrane Antigen-Specific Antitumor Activity of a Self-Immolative Tubulysin Conjugate. Bioconjug Chem. 2019 Jun 19;30(6):1805-1813.

[2]. Vlahov IR, et al. Acid mediated formation of an N-acyliminium ion from tubulysins: a new methodology for the synthesis of natural tubulysins and their analogs. Bioorg Med Chem Lett. 2011 Nov 15;21(22):6778-81.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
978.0±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C42H63N5O10S

[ Molecular Weight ]:
830.042

[ Flash Point ]:
545.3±34.3 °C

[ Exact Mass ]:
829.429565

[ LogP ]:
5.78

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.552

Related Compounds