Preparation of fluorescent labeled gentamicin as biological tracer and its characterization by liquid chromatography and high resolution mass spectrometry

Journal of Pharmaceutical and Biomedical Analysis
Ulrich WoiwodeMichael Lämmerhofer

Abstract

This work deals with the preparation of single-labeled bioconjugates of the antibiotic Gentamicin (GT) with the sulforhodamine-derived fluorescence dye Texas Red(®)-X (TR), its purification by high-performance liquid chromatography (HPLC) and its characterization by high-resolution mass spectrometry. Aminoglycosides such as GT are efficient antibiotics, but also problematic due to severe side effects such as nephro- and ototoxicity. Fluorescent labeled GT is used to visualize cellular uptake and distribution of the antibiotic to finally understand the mechanisms of serious adverse drug reactions. Pharmaceutically administered GT is a mixture of mainly four different components, which exhibit three (GT(C1)) or four (GT(C1a), GT(C2), GT(C2a)) primary amino functional groups which can be coupled with the labeling reagent TR. Thus, multiple labeling could be envisaged which was assumed to be detrimental for uptake studies by fluorescence imaging. The proposed synthesis aimed at preparation of single labeled product and together with the employed purification strategy indeed yielded single labeled GT as product. Analytical control of the reaction product was carried out by means of mass spectrometry (UHPLC-ESI-QTOF-MS/MS) to rule ou...Continue Reading

References

Mar 1, 1989·Toxicology Letters·P M Tulkens
Nov 21, 1998·The EMBO Journal·S YoshizawaJ D Puglisi
Nov 8, 2003·Journal of the Association for Research in Otolaryngology : JARO·P S SteygerC F Dai
Jun 1, 2005·Hearing Research·Sigrid E MyrdalPeter S Steyger
Feb 3, 2007·Current Pharmaceutical Design·Erol Selimoglu
Sep 28, 2007·Journal of the Association for Research in Otolaryngology : JARO·Sofia Lyford-PikeJohn P Carey
Jul 7, 2009·Journal of Pharmaceutical and Biomedical Analysis·Rok Grahek, Lucija Zupancic-Kralj
Jan 5, 2011·Audiology & Neuro-otology·Ja-Won KooPeter S Steyger
Feb 15, 2011·Journal of Pharmaceutical and Biomedical Analysis·B LiE Adams
Oct 20, 2011·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·D Hurtaud-PesselE Verdon
Jan 28, 2012·Journal of Separation Science·Praveen KumarFrancesc Centrich
Dec 25, 2012·Journal of Pharmaceutical and Biomedical Analysis·Yao-zuo YuanErwin Adams
May 7, 2014·Journal of Separation Science·Jie WeiXinmiao Liang

❮ Previous
Next ❯

Related Concepts

Related Feeds

Bioinformatics in Biomedicine

Bioinformatics in biomedicine incorporates computer science, biology, chemistry, medicine, mathematics and statistics. Discover the latest research on bioinformatics in biomedicine here.

Aminoglycosides (ASM)

Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside. Discover the latest research on aminoglycoside here.

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Aminoglycosides

Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside. Discover the latest research on aminoglycoside here.

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.