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 accomm ...

), 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 t ...

), is a

cytotoxic agent Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are toxic metals, toxic chemicals, microbe neurotoxins, radiation particles and even specific neurotransmitters when the system is out of balance. Also some types of dru ...

. It inhibits the assembly of

microtubule Microtubules are polymers of tubulin that form part of the cytoskeleton and provide structure and shape to eukaryotic cells. Microtubules can be as long as 50 micrometres, as wide as 23 to 27 nanometer, nm and have an inner diameter bet ...

s 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 the fungus '' Rhizopus microsporus'' which causes rice seedling blight. Biosynthesis Rhizoxin is biosynthesised by '' Paraburkholderia rhizoxinica'', a bacterial end ...

binding site.National Cancer Institute: Definition of Maytansine
/ref> The maytansine binding site and binding mode has been characterized. It is a

macrolide Macrolides are a class of mostly natural products with a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached. Macrolides belong to the polyketide class of natural products. ...

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 ...

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

Maytenus ''Maytenus'' is a genus of flowering plants in the family Celastraceae. Members of the genus are distributed throughout Central America, Central and South America, Southeast Asia, Micronesia, and Australasia, the Indian Ocean and Africa. They gr ...

''.

Maytansinoids

Derivatives of maitansine are known as maytansinoids. Some are being investigated as the cytotoxic component of antibody-drug conjugates 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 c ...

is an approved drug for the treatment of certain kinds of

breast cancer Breast cancer is a cancer that develops from breast tissue. Signs of breast cancer may include a Breast lump, lump in the breast, a change in breast shape, dimpling of the skin, Milk-rejection sign, milk rejection, fluid coming from the nipp ...

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 anti ...

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

References

Ansamycins Epoxides Chlorine-containing natural products Lactams Chlorobenzene derivatives Acetamides Microtubule inhibitors Carbamates Plant toxins {{antineoplastic-drug-stub

Maytansinoids

See also

References