Phleomycin D1

Structural formula
General
Surname	Phleomycin D1
other names	Zeocin; N 1- [4 - [(Aminoiminomethyl) amino] butyl] -7,8-dihydro-bleomycinamide;
Molecular formula	C 55 H 86 N 20 O 21 S 2 ; C 55 H 86 N 20 O 21 S 2 Cu · HCl (copper chelate complex) ;
Brief description	bluish powder (as a copper chelate complex)
External identifiers / databases
PubChem	71668282
Wikidata	Q969337
properties
Molar mass	1427.52 g · mol -1
safety instructions
GHS labeling of hazardous substances Phleomycin; Caution
H and P phrases	H: 302
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phleomycin D1 is a copper chelating glycopeptide antibiotic . It is best known under the trade name Zeocin, which mainly contains phleomycin D1. It belongs to the bleomycin family and is also isolated from a mutant of Streptomyces verticillus . The mechanism of action is not yet fully understood, but Zeocin has a wide range of target organisms ( prokaryotes and eukaryotes ).

properties

The copper complex creates crystals with a bluish color. Phleomycin D1 loses its activity in the acidic and basic range as well as in the presence of oxidative reagents.

use

Phleomycin D1 is mainly used in molecular biology research. The big advantage is that B. not only works against bacteria or yeast, but against both. This enables the use of vectors for cloning experiments that are suitable for bacteria and yeast and so only one resistance gene is necessary for the selection .

Mode of action

The mode of action not yet fully understood. However, it is believed that phleomycin D1 penetrates the cell and intercalates the DNA . The metal ions (copper) then split the DNA. The cell's genetic material is damaged and it is no longer able to survive.

Mode of action of resistance

The resistance gene Sh ble enables the cell to express a 14 kDa protein which binds to phelomycin D1 in a highly specific manner. As a result, the antibiotic is inhibited and ineffective.

Web links

Invivogen: Zeocin product sheet (PDF; 167 kB)
Entry on Phleomycin D1 in the ChemIDplus database of the United States National Library of Medicine (NLM)

Individual evidence

↑ ^a ^b ^c ^d data sheet Phleomycin from Streptomyces verticillus at Sigma-Aldrich , accessed on May 12, 2017 ( PDF ).

[Sigma-1] ta sheet Phleomycin from Streptomyces verticillus at Sigma-Aldrich , accessed on May 12, 2017 ( PDF ).