| Evaluation of the brain-specific delivery of radioiodinated (iodophenyl)alkyl-substituted amines coupled to a dihydropyridine carrier. | |
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MedLine Citation:
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PMID: 4067987 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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To evaluate the potential usefulness of radioiodinated phenylamines attached to dihydropyridine carriers as a means of brain-specific delivery of radiopharmaceuticals, 1-methyl-3-[N-[beta- (4-[125I]iodophenyl)ethyl]carbamoyl]-1,4-dihydropyridine ([125I]-9) and 1-methyl-3-[N-(4-[125I]iodophenyl)carbamoyl]-1,4-dihydropyridine ([125I]-13) have been prepared by dithionite reduction of the corresponding pyridinium precursors, [125I]-8 and [125I]-12, respectively. Formation of 8 involved coupling of (p-aminophenyl)ethylamine with N-succinimidyl (1-methyl-3-pyridinio)formate iodide (4) followed by transformation to the corresponding N-piperidinyl- (6) or (diethylamino)- (7) triazines that were converted to 8 by treatment with HI. Alternatively, 12 was prepared by initial conversion of (4-amino-phenyl)mercuric acetate (10) to 4-iodoaniline (11) by treatment with I2 and then coupling with 4. The radioiodinated quaternary products, 8 and 12, showed low brain uptake and low brain to blood ratios, whereas the dihydropyridine analogues, 9 and 13, showed comparatively good brain uptake and good brain to blood ratios in rats. These data demonstrate that dihydropyridine-coupled radiopharmaceuticals can cross the blood-brain barrier and the technique may be useful for the measurement of cerebral blood perfusion. |
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Authors:
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M L Tedjamulia; P C Srivastava; F F Knapp |
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Publication Detail:
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Type: Comparative Study; Journal Article; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 28 ISSN: 0022-2623 ISO Abbreviation: J. Med. Chem. Publication Date: 1985 Nov |
Date Detail:
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Created Date: 1985-12-27 Completed Date: 1985-12-27 Revised Date: 2008-11-21 |
Medline Journal Info:
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Nlm Unique ID: 9716531 Medline TA: J Med Chem Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 1574-80 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Blood-Brain Barrier Brain / metabolism* Chemical Phenomena Chemistry Dihydropyridines* Female Iodine Radioisotopes Iodobenzenes / blood, chemical synthesis, metabolism* Pyridines / blood, chemical synthesis, metabolism* Pyridinium Compounds / blood, chemical synthesis, metabolism* Rats Rats, Inbred Strains |
| Chemical | |
Reg. No./Substance:
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0/Dihydropyridines; 0/Iodine Radioisotopes; 0/Iodobenzenes; 0/Pyridines; 0/Pyridinium Compounds; 97807-21-1/1-methyl-3-(N (4-iodophenylethyl)carbamoyl)pyridinium; 97807-23-3/1-methyl-3-(N-(4-iodophenylethyl)carbamoyl)-1,4-dihydropyridine; 97807-25-5/1-methyl-3-(N-(4-iodophenyl)carbamoyl)pyridinium iodide; 97807-27-7/1-methyl-3-(N-(4-iodophenyl)carbamoyl)-1,4-dihydropyridine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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