Tubulysin A
CAS Number: 253392-12-8
Molecular Formula: CHNO
Molecular Weight: 646.81 g/mol
Appearance: White to off-white solid / powder
Purity (HPLC): 95%
Tubulysin A is one of the most studied members of the tubulysin family a group of highly cytotoxic natural products known for their potent anti-mitotic activity. These compounds are isolated from myxobacteria such as Archangium gephyra and Angiococcus disciformis.
Tubulysin A OverviewFeature | Details |
---|---|
Class | Tetrapeptide cytotoxin |
Source | Myxobacteria |
Mechanism | Microtubule depolymerization |
Potency | Extremely high (picomolar range) |
Use | Research tool, payload in ADCs |
Tubulysin A is a tetrapeptide made up of:
N-Methylpipecolic acid (Mep)
Isoleucine (or a variant)
Tubuvaline (Tuv) Contains a thiazole and a methylated hydroxyl group
Tubutyrosine (Tut) A highly modified tyrosine residue
These unusual building blocks give Tubulysin A its:
Hydrophobic character
High binding affinity to tubulin
Resistance to proteolysis
Binds to tubulin and inhibits microtubule polymerization
Causes mitotic arrest in the G2/M phase
Triggers apoptosis through mitochondrial pathways
It works similarly to agents like vinblastine, but is ~1001000 more potent.
Therapeutic RelevanceTubulysin A is too toxic for direct systemic use, but:
It is used in Antibody-Drug Conjugates (ADCs) as a cytotoxic payload
Derivatives and synthetic analogs are being developed for targeted cancer therapy
Notable for its effectiveness against drug-resistant cancer cells
Synthesized by non-ribosomal peptide synthetases (NRPS) and polyketide synthase (PKS) hybrid systems
The complex biosynthetic gene cluster encodes tailoring enzymes for methylation, oxidation, and cyclization
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