What is Maytansine？

Description

Maytansine is a pharmacologically active 19-membered ansamacrolide derived from various medicinal plants and microorganisms[1]. Its discovery in the 1970s in Maytenus and Putterlickia plants. It is an important antineoplastic and antimicrobial compound with high cytotoxicity.

Preparation

Maytansine is a compound of class benzoansamacrolide present in various botanical and microbial sources. It can be isolated from the Indian plant(T. nudiflora), M. buchananii, and seeds of the M. rothia plant. Although maytansine was originally isolated from the Celastraceae plant, it was later shown to be a metabolite of endophytic microorganisms. In 2014, Kusari et al. conducted a study of the Putterlickia species and found that the endophytic microbial community colonizing the root cortex was converting ansamitocin to maytansine, which was then taken up by the plant[2].

Uses

Maytansine is a heterocyclic organic compound. It can bind to the rhizoxin binding sites of tubulin, thereby hindering the assembly of microtubules, leading to the decomposition of microtubules, and achieving the purpose of inhibiting cell division[3]. It shows cytotoxic effects on a variety of tumor cell lines in vivo, inhibiting tumor growth and proliferation. Maytansine derived from plants and microbes also has antimicrobial properties. However, maytansine has toxic side effects on the gastrointestinal and nervous systems, which limits its use in cancer treatment. To solve this problem, the researchers designed the antibody-drug conjugate drug. Designed to enhance the therapeutic potential of maytansine and reduce its toxic side effects by selectively targeting and destroying cancer cells. After a conjugate drug binds to its specific receptor, it enters the cell through endocytosis. Maytansine is then isolated from the antibody, and free metaline alters the microtubule dynamics[4].

References

[1] Eckelmann D, et al. Spatial profiling of maytansine during the germination process of Maytenus senegalensis seeds. Fitoterapia, 2017; 119: 51-56.

[2] Zafar S, et al. New insights into the anticancer therapeutic potential of maytansine and its derivatives. Biomedicine Pharmacotherapy, 2023; 165: 115039.

[3] Cao S, et al. Tubulin Maytansine Site Binding Ligands and their Applications as MTAs and ADCs for Cancer Therapy. Current Medicinal Chemistry, 2020; 27: 4567-4576.

[4] LUDUENA R, et al. Interactions of Vinblastine and Maytansine with Tubulin. Annals of the New York Academy of Sciences, 1986; 466: 718-732.

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