Pyocyanin
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| General | ||||||||||||||||
| Surname | Pyocyanin | |||||||||||||||
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| Molecular formula | C 13 H 10 N 2 O | |||||||||||||||
| Brief description |
blue-green pigment |
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| properties | ||||||||||||||||
| Molar mass | 210.23 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| Melting point |
133 ° C |
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| solubility |
soluble in ethanol, DMSO, acetone and chloroform |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Pyocyanine is a chemical compound from the group of phenazine derivatives .
history
In 1859 the pharmacist Mathurin-Joseph Fordos was able to isolate the pigment from the blue-colored pus after long wound care. He coined the common name , composed of the Greek words for pus and cyan . Two decades later (1882) Carle Gessard was able to show that Pseudomonas aeruginosa produces this substance. The structure of pyocyanine as 5- N -methyl-1-hydroxyphenazinium betaine was clarified in 1938.
Occurrence
Pyocyanin occurs naturally in the Gram-negative bacterium Pseudomonas aeruginosa . It is believed to serve as a respiratory pigment and virulence factor to generate reactive oxygen species .
use
Pyocyanin is an antibacterial dye. Due to its reductive properties, pyocyanine creates oxidative stress in bacteria and mammalian cells.
Individual evidence
- ↑ a b c d e f g sheet pyocyanin, from at Sigma-Aldrich , accessed on 10 March 2012 ( PDF ).
- ↑ a b Christina Diederich, Mario Leypold, Rolf Breinbauer, Wulf Blankenfeldt: Biosynthesis of Phenazines. In: News from chemistry. 62, 2014, pp. 975-980, doi : 10.1002 / nadc.201490357 .
- ^ Hassan HM, Fridovich I : Mechanism of the antibiotic effect of pyocyanine . In: J Bacteriol . 141, No. 1, 1980, pp. 156-163. PMID 6243619 . PMC 293551 (free full text).
- ↑ Muller M .: Pyocyanin induces oxidative stress in human endothelial cells and modulates the glutathione redox cycle . In: Free Radic Biol Med . 33, No. 11, 2002, pp. 1527-1533. doi : 10.1016 / S0891-5849 (02) 01087-0 . PMID 12446210 .