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T3327

Sigma-Aldrich

Tubulysin A

≥95% (HPLC), from Streptomyces sp., film

Synonym(s):

TubA

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About This Item

Empirical Formula (Hill Notation):
C43H65N5O10S
CAS Number:
205304-86-5
Molecular Weight:
844.07
MDL number:
MFCD12912448
UNSPSC Code:
12352202
PubChem Substance ID:
329826749

biological source

Streptomyces sp.

Quality Level

100

Assay

≥95% (HPLC)

form

film

color

colorless to white

solubility

organic solvents: soluble

shipped in

wet ice

storage temp.

2-8°C

SMILES string

CC[C@H](C)[C@H](NC(=O)[C@H]1CCCCN1C)C(=O)N(COC(=O)CC(C)C)[C@H](C[C@@H](OC(C)=O)c2nc(cs2)C(=O)N[C@H](C[C@H](C)C(O)=O)Cc3ccc(O)cc3)C(C)C

InChI

1S/C43H65N5O10S/c1-10-27(6)38(46-40(53)34-13-11-12-18-47(34)9)42(54)48(24-57-37(51)19-25(2)3)35(26(4)5)22-36(58-29(8)49)41-45-33(23-59-41)39(52)44-31(20-28(7)43(55)56)21-30-14-16-32(50)17-15-30/h14-17,23,25-28,31,34-36,38,50H,10-13,18-22,24H2,1-9H3,(H,44,52)(H,46,53)(H,55,56)/t27-,28-,31+,34+,35+,36+,38-/m0/s1

InChI key

IBEDDHUHZBDXGB-OEJISELMSA-N

Biochem/physiol Actions

Tubulysin A is a myxobacterial product that can function as an antiangiogenic agent in many in vitro assays1.
Tubulysin A is a novel antibiotic, which is anti-microtubule, anti-mitotic, apoptosis inducer, anticancer, anti-angiogenic, and antiproliferative.
Tubulysin A is a novel antibiotic, which is anti-microtubule, anti-mitotic, apoptosis inducer, anticancer, anti-angiogenic, and antiproliferative. Tubulysins are cytotoxic peptides, which include 9 members (A-I). Tubulysin A has potential application as an anticancer agent. It arrests cells in the G2/M phase. Tubulysin A inhibits polymerization more efficiently than vinblastine and induces depolymerization of isolated microtubules. Tubulysin A has potent cytostatic effects on various tumor cell lines with IC50 in the picomolar range.

Preparation Note

Tubulysin A is soluble in organic solvents.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
111M4726V
018K4710

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Gurmeet Kaur et al.
The Biochemical journal, 396(2), 235-242 (2006-02-24)
Tubulysin A (tubA) is a natural product isolated from a strain of myxobacteria that has been shown to depolymerize microtubules and induce mitotic arrest. The potential of tubA as an anticancer and antiangiogenic agent is explored in the present study.
Lindsay M Steirer et al.
PloS one, 6(11), e27249-e27249 (2011-11-19)
Polysialic acid (PSA), an α2,8-linked homopolymer of N-acetylneuraminic acid (Neu5Ac), is developmentally regulated and its expression is thought to be restricted to a few tissues in adults. Recently, we showed that two human pathogens expressed a derivative of PSA containing
Christina M Van Itallie et al.
Molecular biology of the cell, 26(15), 2769-2787 (2015-06-13)
Assembly and sealing of the tight junction barrier are critically dependent on the perijunctional actin cytoskeleton, yet little is known about physical and functional links between barrier-forming proteins and actin. Here we identify a novel functional complex of the junction

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