Synthesis of amphiphilic chelating agents : Bis(hexadecylamide) and bis(octadecylamide) of diethylenetriaminepentaacetic Acid.

Keywords:Imaging agents / Contrast agents / Lanthanides / Micelles / N,O ligands / NMR spectroscopy DTPA-bisamide derivatives with alkyl chains containing 14, 16 and 18 carbon atoms were synthesized and complexes of various trivalent lanthanide ions (Ln = Gd, La, Pr, Eu) were formed. Variable temperature proton NMR spectroscopy of paramagnetic praseodymium(III) and europium(III) complexes revealed that long aliphatic substituents considerably increase the energy barrier for the intramolecular rearrangement around the lanthanide ion. The gadolinium(III) complexes were incorporated into mixed micelles, and photon correlation spectroscopy showed that the mean sizes of all the micelles were within the same range. The NMRD curves of all three DTPA-bisamide-gadolinium complexes incorpor-

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“…[43] DTPA-BC14, DTPA-BC16 and DTPA-BC18 were prepared by the method of Jasanda and Nepveu. [44] Analytical Data for the Ligands DTPA-BC14: 1 …”

Section: Instrumentsmentioning

confidence: 99%

Potential MRI Contrast Agents Based on Micellar Incorporation of Amphiphilic Bis(alkylamide) Derivatives of [(Gd−DTPA)(H₂O)]²⁻

et al. 2003

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“…1,11-Bis(octadecylamino)-1,11-dioxo-6-aza-3,6,9-tris(carboxymethyl)undecane (DTPA-18) was synthesized and purified by modifications of a previously reported procedure (19,20). All materials were reagent grade.…”

Section: Synthesis Of the Chelating Agentmentioning

confidence: 99%

Lanthanide Chelates as Bilayer Alignment Tools in NMR Studies of Membrane-Associated Peptides

Prosser

Bryant

et al. 1999

Journal of Magnetic Resonance

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“…LDL. 29 Previous in vitro experiments 20 had demonstrated the stability of the lipophilic anchorage of the ligand L and the stability of the metal complexation on the L-LDL conjugates in plasma.…”

Section: Discussionmentioning

confidence: 99%

¹¹¹In–L–LDL and ¹⁵³Gd–L–LDL as radiotracers for detection of AR4‐2J rat pancreatic tumors

Ratovo

Souchard

Urizzi

et al. 2003

Applied Organom Chemis

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Pancreatic cancer has an extremely poor prognosis, due, in part, to lack of methods for early diagnosis. The present study was designed to evaluate the potential of labeling low-density lipoprotein (LDL) with a radionuclide using a lipid chelating agent, bis(stearylamide) of diethylenetriaminepentaacetic acid (L), to detect pancreatic tumors by gamma-scintigraphy. Previous studies indicated that the difficulty of visualization of pancreatic tumors was due to their poor vascularization. This study compares the ability of two radiotracers, 111 In-L-LDL and 153 Gd-L-LDL to target highly vascularized rat pancreatic tumors (AR4-2J) implanted in nude mice. Biodistribution studies showed that the tumor uptake of 111 In-L-LDL and 153 Gd-L-LDL tracers was twofold and fivefold higher respectively than with the controls ( 111 In citrate and 153 Gd citrate respectively). These tracers would thus be suitable for scintigraphic imaging.We show here that LDL could be employed as a delivery system for tracers such as 111 In or 153 Gd when these two radionuclides are complexed by a lipid-chelating anchor, and that 111 In-L-LDL and 153 Gd-L-LDL enabled better visualization of the pancreatic tumor tissues, with a better result with 153 Gd-L-LDL.

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Synthesis of amphiphilic chelating agents : Bis(hexadecylamide) and bis(octadecylamide) of diethylenetriaminepentaacetic Acid.

Cited by 27 publications

References 8 publications

Potential MRI Contrast Agents Based on Micellar Incorporation of Amphiphilic Bis(alkylamide) Derivatives of [(Gd−DTPA)(H₂O)]²⁻

Potential MRI Contrast Agents Based on Micellar Incorporation of Amphiphilic Bis(alkylamide) Derivatives of [(Gd−DTPA)(H₂O)]²⁻

Lanthanide Chelates as Bilayer Alignment Tools in NMR Studies of Membrane-Associated Peptides

¹¹¹In–L–LDL and ¹⁵³Gd–L–LDL as radiotracers for detection of AR4‐2J rat pancreatic tumors

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Synthesis of amphiphilic chelating agents : Bis(hexadecylamide) and bis(octadecylamide) of diethylenetriaminepentaacetic Acid.

Cited by 27 publications

References 8 publications

Potential MRI Contrast Agents Based on Micellar Incorporation of Amphiphilic Bis(alkylamide) Derivatives of [(Gd−DTPA)(H2O)]2−

Potential MRI Contrast Agents Based on Micellar Incorporation of Amphiphilic Bis(alkylamide) Derivatives of [(Gd−DTPA)(H2O)]2−

Lanthanide Chelates as Bilayer Alignment Tools in NMR Studies of Membrane-Associated Peptides

111In–L–LDL and 153Gd–L–LDL as radiotracers for detection of AR4‐2J rat pancreatic tumors

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Potential MRI Contrast Agents Based on Micellar Incorporation of Amphiphilic Bis(alkylamide) Derivatives of [(Gd−DTPA)(H₂O)]²⁻

Potential MRI Contrast Agents Based on Micellar Incorporation of Amphiphilic Bis(alkylamide) Derivatives of [(Gd−DTPA)(H₂O)]²⁻

¹¹¹In–L–LDL and ¹⁵³Gd–L–LDL as radiotracers for detection of AR4‐2J rat pancreatic tumors