Radioiodinated N-(alkylaminoalkyl)-substituted 4-methoxy-, 4-hydroxy-, and 4-aminobenzamides: biological investigations for the improvement of melanoma-imaging agents.

Abstract:

:The syntheses and radiolabelling of 27 new N-(alkylaminoalkyl)-4-methoxy-, -4-hydroxy-, and -4-aminobenzamides are described and evaluated in C57B1/6 mice with subcutaneously transplanted B16 melanoma in order to screen the optimal chemical structure for melanoma scintigraphy. Using T1(TFA)3 for 131I- labelling, a series of radioiodinated 4-methoxy benzamide derivatives proved to exhibit superior melanoma uptake with outstanding melanoma/non-target-tissue ratios. From the benzamide derivatives tested, N-(2-(1'-piperidinyl)ethyl-3-[131I]iodo-4-methoxybenzamide and N-(2-diethylaminoethyl)-3-[131I]iodo-4-methoxybenzamide demonstrated best results. The introduction of 4-hydroxy and 4-amino groups led to less favourable benzamides. While the former compounds showed little melanoma uptake, the latter revealed unfavourable melanoma/non-target-tissue ratios. Additionally, it could be shown that an amino group was inevitably necessary for melanoma uptake, and that dialkylation of the amide nitrogen and replacing CONH by CH2NH revealed less advantageous results.

journal_name

Nucl Med Biol

authors

Mohammed A,Nicholl C,Titsch U,Eisenhut M

doi

10.1016/s0969-8051(97)00024-3

subject

Has Abstract

pub_date

1997-07-01 00:00:00

pages

373-80

issue

5

eissn

0969-8051

issn

1872-9614

pii

S0969-8051(97)80002-9

journal_volume

24

pub_type

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