New method for recognition of sterol signalling molecules: methinium salts as receptors for sulphated steroids
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
25478679
DOI
10.1016/j.steroids.2014.10.009
PII: S0039-128X(14)00277-3
Knihovny.cz E-resources
- Keywords
- Molecular recognition, Polymethinium salts, Sulphated sterols, Synthetic receptors,
- MeSH
- Benzothiazoles chemistry MeSH
- Cholesterol Esters chemistry pharmacology MeSH
- Estrone analogs & derivatives chemistry pharmacology MeSH
- Heterocyclic Compounds chemistry pharmacology MeSH
- Carbocyanines chemistry MeSH
- Mice, Nude MeSH
- Breast Neoplasms drug therapy MeSH
- Pregnenolone chemistry pharmacology MeSH
- Antineoplastic Agents pharmacology MeSH
- Xenograft Model Antitumor Assays MeSH
- Animals MeSH
- Check Tag
- Female MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- benzothiazole MeSH Browser
- Benzothiazoles MeSH
- cholesteryl sulfate MeSH Browser
- Cholesterol Esters MeSH
- Estrone MeSH
- estrone sulfate MeSH Browser
- Heterocyclic Compounds MeSH
- Carbocyanines MeSH
- Pregnenolone MeSH
- Antineoplastic Agents MeSH
In this work, we studied indolium and benzothiazolium pentamethine salts 1-3 as novel type of receptors for the recognition of sulphated signalling molecules (sulphated steroids: oestrone, pregnenolone and cholesterol sulphate). A recognition study was performed in an aqueous medium (1mM phosphate buffer (H2O:MeOH; 99:1 (v/v))) at pH 7.34. The tested salts displayed a high affinity for these sulphated analytes, mainly for cholesterol sulphate. However, no interaction between the salts and control, non-sulphated sterol analytes (cholesterol and bile acid) was observed. The highest affinity for the sulphated steroids was observed for benzothiazole salt 1. This salt also displayed different spectral behaviour from that observed for carbocyanine salts 2 and 3. In this presence of cholesterol sulphate, benzothiazole salt 1 displayed significant spectral changes depending on the medium used: a blue shift in the aqueous medium and a red shift in the methanolic one (H2O:MeOH; 2:1 (v/v)). Subsequently preliminary in vivo study showed that, salt 1 significantly inhibits a growth of breast carcinoma on Nu/nu mice model.
References provided by Crossref.org
Cyanine dyes in the mitochondria-targeting photodynamic and photothermal therapy
