Labelled psoralens. Synthesis of 4′‐aminomethyltrioxsalen‐3‐t

Abstract

SUMMARYBromination of 4'-phthalimidomethyltrioxsalen (3) provided the 3-monobromo derivative (4) which on hydrogenolysis with either deuterium or tritium provided the corresponding labelled derivatives Removal of the phthalimide moiety from 6 produced the title compound (2) having specific activity of 7.46 Ci/mmole. and 5.

Psoralens as Photoactive Probes of Nucleic Acid Structure and Function: Organic Chemistry, Photochemistry, and Biochemistry

“…Both tritium and carbon-14 labeled psoralens have been synthesized by routine synthetic manipulation to obtain radiolabeled derivatives. Methods used include exchange reactions with tritium gas (88,89) and tdtiated water (25), catalytic reduction (80,81) and hydrogenolysis tritium gas (90), alkylation with tritium (80,81) or carbon-14 labeled alkyl halides, borotritide reductions of aldehydes and ketones (80), and various ring syntheses with carbon-14 labeled precursors (47). The exchange procedures typically give low specific activities (50-300 mCi/mmol) and do not sitespecifically label the molecule.…”

The reaction of the psoralens with deoxyribonucleic acid

“…The synthesis of (3-3 H 1 )-4'-aminomethyl-4,5',8-trimethylpsoralen (AMT) by hydrogenolysis of 3-bromo-4'-phthalimidomethyl-4,s',8trimethylpsoralen has been reported. Hydrazinolysis of this compound yielded labelled AMT with a specific activity of 7-46 Ci/mmol (Liebman & Delaney, 1981). Table 2 contains a summary of label position, specific activity, and method of preparation of several labelled psoralens.…”