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

Winstead, Meldrum B. and Dougherty, Dennis A. and Lin, Tz-Hong and Khentigan, Archie and Lamb, James F. and Winchell, H. Saul (1978) Relationship of molecular structure to in vivo scintigraphic distribution of carbon-11-labeled compounds. 4. Carbon-11-labeled mandelonitriles, mandelic acids and their esters. Journal of Medicinal Chemistry, 21 (2). pp. 215-217. ISSN 0022-2623. https://resolver.caltech.edu/CaltechAUTHORS:20200612-135405796

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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 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 redistribution to the parotids and stomach with the [¹¹C]hydroxymandelonitriles. ¹¹C-Labeled mandelic acid 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 were synthesized from [¹¹C]mandelic acid. These esters showed initial accumulation of activity in the lungs with eventual excretion by the kidneys.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jm00200a014DOIArticle
ORCID:
AuthorORCID
Dougherty, Dennis A.0000-0003-1464-2461
Additional Information:© 1978 American Chemical Society. Received August 26, 1977. The authors thank Eric Knutson, Michael Rogal, and Richard Stechel of Bucknell University and Michael Garrett, Yu Cheun Lee, Chris Coyle, and Dennis Lum of Medi-Physics for their contribution to this study. This work was supported in part by Atomic Energy Commission Contract AT(04-3)-849 to Medi-Physics, Inc., and by the National Science Foundation Undergraduate Research Participation Program, the Camille and Henry Dreyfus Foundation, Inc., and the National Institutes of Health Grant GM 20073 to Bucknell University. This paper was presented at the 9th Middle Atlantic Regional Meeting of the American Chemical Society, Wilkes-Barre, Pa., April 23-26, 1974.
Funders:
Funding AgencyGrant Number
Atomic Energy CommissionAT(04-3)-849
NSFUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
NIHGM 20073
Issue or Number:2
Record Number:CaltechAUTHORS:20200612-135405796
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200612-135405796
Official Citation:Meldrum B. Winstead, Dennis A. Dougherty, Tz-Hong Lin, Archie Khentigan, James F. Lamb, and H. Saul Winchell Journal of Medicinal Chemistry 1978 21 (2), 215-217 DOI: 10.1021/jm00200a014
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:103884
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:12 Jun 2020 21:45
Last Modified:12 Jun 2020 21:45

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