Endiine

Basic structure of the enediine. R ¹ to R ⁴ : H or organic radicals

Enediynes are a class of bacterial , cyclic natural products that belong to the cycloalkenes and diynes . Characteristic here the nine or ten rings containing a carbon -Kohlenstoff- double bond between two corresponding triple bonds contained. Due to this structural motif, these compounds are able to enter into a Bergman cyclization and can thereby damage the DNA . The resulting diradical leads to a double-strand break in the DNA. This property makes this class of compounds interesting as a chemotherapeutic agent against cancer; today some of them are in the clinical phase. Neocarzinostatin is already used clinically in Japan today.

Structure of esperamicin

Structure of calicheamicin

Various natural substances or types are known that have the structural motif of the enediynes:

Individual evidence

Jump up ↑ S Walker, R Landovitz, WD Ding, GA Ellestad, and D Kahne: Cleavage behavior of calicheamicin gamma 1 and calicheamicin T , in: Proc. Natl. Acad. Sci. USA , 1992 May 15; 89 (10): pp. 4608-4612; PMC 49132 (free full text).
↑ Designed Enediyne Antitumor Agents. .
^ Mukesh C. Joshi, Diwan S. Rawat: Recent Developments in Enediyne Chemistry. In: Chemistry & Biodiversity , 2012, Vol. 9 (3), pp. 459-498; doi : 10.1002 / cbdv.201100047

[1] Jump up ↑ S Walker, R Landovitz, WD Ding, GA Ellestad, and D Kahne: Cleavage behavior of calicheamicin gamma 1 and calicheamicin T , in: Proc. Natl. Acad. Sci. USA , 1992 May 15; 89 (10): pp. 4608-4612; PMC 49132 (free full text).

[2] Designed Enediyne Antitumor Agents. .

[3] Mukesh C. Joshi, Diwan S. Rawat: Recent Developments in Enediyne Chemistry. In: Chemistry & Biodiversity , 2012, Vol. 9 (3), pp. 459-498; doi : 10.1002 / cbdv.201100047