Magn Reson Med. 1991 Nov;22(1):57-67. doi: 10.1002/mrm.1910220107.

Fatty-acyl iminopolycarboxylates: lipophilic bifunctional contrast agents for NMR imaging.

Magnetic resonance in medicine

S K Kim, G M Pohost, G A Elgavish

PMID: 1798395 DOI: 10.1002/mrm.1910220107

Abstract

New fatty-acyl contrast agents, N3-2'-myristoyloxyethyl-N6-2'-hydroxyethyl-1, 8-dioxotriethylenetetraamine-N,N,N',N'-tetraacetic acid (MHE-DTTA) and N3,N6-bis(2'-myristoyloxyethyl)-1,8-dioxo- triethylenetetraamine-N,N,N',N'-tetraacetic acid (BME-DTTA) were prepared by sequential alkylation, acylation, and catalytic hydrogenation from bis(hydroxyethyl)-ethylenediamine with satisfactory yields (overall 36-46%). The 1:1 gadolinium complexes of the ligands MHE-DTTA and BME-DTTA were incorporated into liposomes and their relaxivities in vitro were determined. The relaxivities of both agents were similar and were greater than those of Gd3+ aquoion, Gd(EDTA), and Gd(DTPA) at both 0.23 T and 0.47 T. The relaxivities of these two agents increased from the lower to the higher magnetic field, indicating a positive field dependence. This is advantageous because of the widespread use of high-field (B0 greater than 0.5 T) NMR imaging instruments. Stability constants (log K) of Gd(MHE-DTTA) and Gd(BME-DTTA) were found to be 15.27 +/- 2.21 and 16.78 +/- 0.36, respectively. LD50 of both compounds was greater than 0.2 mmol/kg. These stabilities and lower limits of LD50 indicate the possible in vivo application of these agents.

Similar articles

Substances

• Contrast Media
• Liposomes
• N(3)-2'-myristoyloxyethyl-N(6)-2'-hydroxyethyl-1,8-dioxotriethylenetetramine-N,N,N',N'-tetraacetic acid
• N(3),N(6)-bis(2'-myristoyloxyethyl)-1,8-dioxotriethylenetetramine-N,N,N',N'-tetraacetic acid
• Pentetic Acid
• Gadolinium
• Gadolinium DTPA

MeSH terms

• Animals
• Contrast Media*
• Gadolinium
• Gadolinium DTPA
• Liposomes
• Magnetic Resonance Imaging*
• Pentetic Acid / analogs & derivatives
• Pentetic Acid / chemical synthesis
• Pentetic Acid / toxicity
• Rats
• Rats, Inbred Strains

Publication Types

• Journal Article
• Research Support, U.S. Gov't, P.H.S.

Grant support

• P01 HL7667/HL/NHLBI NIH HHS/United States
• R01 HL33200/HL/NHLBI NIH HHS/United States

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