Relationship of molecular structure to in vivo scintigraphic distribution of carbon-11-labeled compounds. 4. Carbon-11-labeled mandelonitriles, mandelic acids and their esters

Abstract

11C-Labeled HCN was collected in water containing carrier KCN following bombardment of 99% N2-1% H2 with 22 MeV protons. 11C-Labeled mandelonitrile [antitumor agent] and p-methoxy-, p-hydroxy- and 3,4-dihydroxymandelonitrile were synthesized from K11CN and the corresponding benzaldehyde. The initial distribution of 11C activity of these nitriles in dogs was primarily in the region of the heart, liver and kidneys followed by rapid re-distribution to the parotids and stomach with the [11C]hydroxymandelonitriles. 11C-Labeled mandelic acid [urinary antiseptic agent] and m-methyl-, o-chloro- and p-chloromandelic acid were synthesized from the corresponding [11C]mandelonitrile. Serial scintigraphy of 11C activity of these mandelic acids in dogs showed progressive renal excretion with accumulation of activity in the bladder. 11C-Labeled ethyl and benzyl mandelate [antispasmodic agents] were synthesized from [11C]mandelic acid. These esters showed initial accumulation of activity in the lungs with eventual excretion by the kidneys.