Maitansine (

INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they also provided accommo ...

), or maytansine (

USAN 280px, "Samguk Sagi" Book 04. Silla's Records. In 512, Usan-guk（于山國）was Ulleungdo（鬱陵島） Usan-guk, or the State of Usan, occupied Ulleung-do and the adjacent islands during the Korean Three Kingdoms period. According to the ...

), is a

cytotoxic agent Cytotoxicity is the quality of being toxicity, toxic to cell (biology), cells. Examples of toxic agents are an immune cell or some types of venom, e.g. from the Bitis arietans, puff adder (''Bitis arietans'') or brown recluse spider (''Loxosceles r ...

. It inhibits the assembly of microtubules by binding to

tubulin Tubulin in molecular biology can refer either to the tubulin protein superfamily of globular proteins, or one of the member proteins of that superfamily. α- and β-tubulins polymerize into microtubules, a major component of the eukaryotic cytosk ...

at the

rhizoxin Rhizoxin is an antimitotic agent with anti-tumor activity. It is isolated from a pathogenic plant fungus ('' Rhizopus microsporus'') which causes rice seedling blight. Biosynthesis Rhizoxin is biosynthesised by ''Burkholderia rhizoxinica'', a ...

binding site.National Cancer Institute: Definition of Maytansine
/ref> It is a

macrolide The Macrolides are a class of natural products that consist of a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. M ...

of the

ansamycin Ansamycins is a family of bacterial secondary metabolites that show antimicrobial activity against many Gram-positive and some Gram-negative bacteria, and includes various compounds, including streptovaricins and rifamycins. In addition, these c ...

type and can be isolated from plants of the genus ''

Maytenus ''Maytenus'' ''Sunset Western Garden Book,'' 1995:606–607 is a genus of flowering plants in the family Celastraceae. Members of the genus are distributed throughout Central and South America, Southeast Asia, Micronesia and Australasia, the Indi ...

''.

Maytansinoids

Derivatives of maitansine are known as maytansinoids. Some are being investigated as the cytotoxic component of

antibody-drug conjugate Antibody-drug conjugates or ADCs are a class of biopharmaceutical drugs designed as a targeted therapy for treating cancer. Unlike chemotherapy, ADCs are intended to target and kill tumor cells while sparing healthy cells. As of 2019, some 56 phar ...

s for cancer treatment, and the antibody-drug conjugate

trastuzumab emtansine Trastuzumab emtansine, sold under the brand name Kadcyla, is an antibody-drug conjugate consisting of the humanized monoclonal antibody trastuzumab (Herceptin) covalently linked to the cytotoxic agent DM1. Trastuzumab alone stops growth of can ...

is an approved drug for the treatment of certain kinds of

breast cancer Breast cancer is cancer that develops from breast tissue. Signs of breast cancer may include a lump in the breast, a change in breast shape, dimpling of the skin, milk rejection, fluid coming from the nipple, a newly inverted nipple, or ...

in the EU and in the US. Examples of maytansinoids are: * Ansamitocin *

Mertansine Mertansine, also called DM1 (and in some of its forms emtansine), is a thiol-containing maytansinoid that for therapeutic purposes is attached to a monoclonal antibody through reaction of the thiol group with a linker structure to create an ant ...

/ emtansine (DM1) * Ravtansine / soravtansine (DM4)

References

Ansamycins Epoxides Halogen-containing natural products Lactams Chlorobenzenes Acetamides Microtubule inhibitors Carbamates Plant toxins {{antineoplastic-drug-stub

Maytansinoids

See also

References