NDLI: Release of Toxic $Gd^{3+}$ Ions to Tumour Cells by $Vitamin B_{12}$ Bioconjugates

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Release of Toxic $Gd^{3+}$ Ions to Tumour Cells by $Vitamin B_{12}$ Bioconjugates

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Release of Toxic $Gd^{3+}$ Ions to Tumour Cells by $Vitamin B_{12}$ Bioconjugates

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Wuerges, Jochen Arena, Francesca Dreos, Renata Geremia, Silvano Siega, Patrizia Gianolio, Eliana Fedosov, Sergey N. Aime, Silvio Randaccio, Lucio
Description	Author Affiliation: Siega P ( Department of Chemical Sciences, Centre of Excellence in Biocrystallography, University of Trieste, Via Licio Giorgieri 1, 32127 Trieste, Italy.)
Abstract	Two probes consisting of $vitamin B_{12}$ (CNCbl) conjugated to Gd chelates by esterification of the ribose 5′-OH moiety, Gd–DTPA–CNCbl (1; DTPA=diethylenetriamine-N,N,N′,N′′,N′′-pentaacetic acid) and Gd–TTHA–CNCbl (2; TTHA=triethylenetetramine-N,N,N′,N′′,N′′′,N′′′-hexaacetic acid), have been synthesised and characterised. The crystal structure of a dimeric form of 1, obtained by crystallisation with an excess of $GdCl_{3},$ has been determined. The kinetics of binding to and dissociation from transcobalamin II show that 1 and 2 maintain high-affinity binding to the $vitamin B_{12}$ transport protein. Complex 2 is very stable with respect to $Gd^{3+}$ release owing to the saturated co-ordination of the $Gd^{3+}$ ion by four amino and five carboxylate groups. Hydrolysis of the ester functionality occurs on the time scale of several hours. The lack of saturation and the possible involvement of the ester functionality in co-ordination result in lower stability of 1 towards hydrolysis and in a considerable release of $Gd^{3+}$ in vitro. $Gd^{3+}$ ions released from 1 are avidly taken up by the K562 tumour cells to an extent corresponding to approximately $10^{10} Gd^{3+}$ per cell. The internalisation of toxic $Gd^{3+}$ ions causes a marked decrease in cell viability as assessed by Trypan blue and WST-1 tests. On the contrary, the experiments with the more stable 2 did not show any significant cell internalisation of $Gd^{3+}$ ions and any influence on cell viability. The results point to new avenues of in situ generation of cytotoxic pathways based on the release of toxic $Gd^{3+}$ ions by $vitamin B_{12}$ bioconjugates.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	32
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-08-10
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Gadolinium DTPA Analogs & Derivatives Gadolinium Toxicity Organometallic Compounds Chemical Synthesis Vitamin B 12 Cations Crystallography, X-Ray Chemistry Pharmacology K562 Cells Molecular Conformation Molecular Structure Tetrazolium Salts Trypan Blue Tumor Cells, Cultured Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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