University of Michigan

Susan W Schwendner

Raymond E Counsell

Karen L Meyer

Terushi Haradahira

Mohamed K Ruyan

Laura E Deforge

Novel radioiodinated analogues of naturally-occurring phospholipid ethers are tumor-specific and have a triglycerol backbone structure which, in certain embodiments, is substituted at the 3-position with an alkyl phosphocholine and include a monoiodinated benzoyl side chain substituted at the 2-position in accordance with the general formula: ##STR1## where n=1-15 ##STR2## M=0-15; Z=.sup.123 I, .sup.125 I, and .sup.131 I; Y=NH.sub.2, NR.sub.2, and NR.sub.3, and R=alkyl, aralkyl.

Radioiodinated phospholipid ether analogues

Novel radioiodinated analogues of naturally-occurring phospholipid ethers are tumor-specific and have a triglycerol backbone structure which, in certain embodiments, is substituted at the 3-position with an alkyl phosphocholine and include a monoiodinated benzoyl side chain substituted at the 2-position in accordance with the general formula: ##STR1## where n= 1-15 ##STR2## m= 0-15; Z=.sup.123 I, .sup.125 I, and .sup.131 I; Y=NH.sub.2, NR.sub.2, and NR.sub.3, and R=alkyl, aralkyl.

Radioiodinated phospholipid ether analogues and methods of using same

Novel radioiodinated analogues of naturally-occurring phospholipid ethers are tumor-specific and have a triglycerol backbone structure which is substituted at the 3-position with an alkyl phosphocholine and include a monoiodinated benzoyl side chain substituted at either the 1- or 2-position. In some embodiments of the invention, the monoiodinated aralkyl side chain may be substituted directly onto alkyl phosphocholine in accordance with general Formula: provided that one and only one of X or Y is a monoiodinated aralkyl ##STR1## where Y=NH.sub.2, NR.sub.2, NR.sub.3, NR.sub.2 R'

Radioiodinated phosphate esters

Novel radioiodinated analogues of naturally occurring phospholipid ethers are tumor-specific to enable selective visualization of neoplastic lesions by gamma-camera scintigraphy. The novel compounds enable a physician to differentiate neoplastic lesions from non-neoplastic lesions in a manner not heretofore available.

Novel radioiodinated analogues of naturally-occurring cholestrol esters, arylaliphatic cholesteryl ethers, are selective for low density lipoproteins and have been shown to be successful imaging agents for adrenal glands. The arylaliphatic cholesteryl ethers have the general formula: ##STR1## where X is a radioactive isotope of iodine and n is an integer between 1 and 20. Two illustrative examples, m-iodobenzyl cholesteryl ether and 12-(m-iodophenyl) dodecyl cholesteryl ether, were radiolabeled with .sup.125 I by an isotope exchange reaction. Tissue distribution studies indicate significant accumulation of the cholesteryl ethers in the adrenal glands, and to a lesser extent in the liver. The cholesteryl ethers selectively incorporate into plasma lipoproteins as determined by polyacrylamide gel electrophoresis.

Growing community of inventors

Ann Arbor, MI, United States of America

Susan W Schwendner