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J Hazard Mater. 2014 Mar 30;269:74-82. doi: 10.1016/j.jhazmat.2014.01.014. Epub 2014 Jan 18.

Synthesis of amphiphilic seleninic acid derivatives with considerable activity against cellular membranes and certain pathogenic microbes.

Author information

1
Division of Bioorganic Chemistry, School of Pharmacy, Saarland University, D-66123 Saarbruecken, Germany.
2
Laboratoire d'Ingénierie Moléculaire et Biochimie Pharmacologique, SRSMC UMR 7565, Université de Lorraine, 1 Boulevard Arago, 57070 Metz, France.
3
Division of Bioorganic Chemistry, School of Pharmacy, Saarland University, D-66123 Saarbruecken, Germany; Department of Food Hygiene, Faculty of Veterinary Medicine, Shahid Bahonar University, Kerman, Iran.
4
Division of Biophysics, Department of Biology, Saarland University, D-66123 Saarbruecken, Germany.
5
Division of Pharmaceutics and Biopharmacy, Philipps University, D-35037 Marburg, Germany.
6
Division of Bioorganic Chemistry, School of Pharmacy, Saarland University, D-66123 Saarbruecken, Germany. Electronic address: c.jacob@mx.uni-saarland.de.

Abstract

Selenium compounds play a major role in Biology, where they are often associated with pronounced antioxidant activity or toxicity. Whilst most selenium compounds are not necessarily hazardous, their often selective cytotoxicity is interesting from a biochemical and pharmaceutical perspective. We have synthesized a series of amphiphilic molecules which combine a hydrophilic seleninic acid head group - which at the same time serves as thiol-specific warhead - with a hydrophobic tail. These molecules possess a surface activity similar to the one of SDS, yet their biological activity seems to exceed by far the one of a simple surfactant (e.g. SDS) or seleninic acid (e.g. phenyl seleninic acid). Such compounds effectively haemolyse Red Blood Cells and exhibit pronounced activity against Saccharomyces cerevisiae. From a chemical perspective, the seleninic warheads are likely to attack crucial cysteine proteins of the cellular thiolstat.

KEYWORDS:

Amphiphile; Cytotoxic activity; Micelle; Seleninic acid; Thiolstat

PMID:
24491370
DOI:
10.1016/j.jhazmat.2014.01.014
[Indexed for MEDLINE]
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