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

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• 作者：Mohammed ; A. ; Nicholl ; C. ; Titsch ; U. ; Eisenhut ; M.
• 关键词：Radioiodinated benzamides ; N-(alkylaminoalkyl)-4-Methoxybenzamides ; N-(alkylaminoalkyl)-4-Hydroxybenzamides ; N-(alkylaminoalkyl)-4-Aminobenzamides ; Organ distribution ; C57Bl/6 mice ; B16 Melanoma
• 刊名：Nuclear Medicine and Biology
• 出版年：1997
• 出版时间：July, 1997
• 年：1997
• 卷：24
• 期：5
• 页码：373-380
• 全文大小：821 K

文摘

The synthesis and radiolabeling of 27 new N-(alkylaminoalkyl)-4-methoxy-, 4-hydroxy-, and -4-aminobenzamides are described and evaluated in C57Bl/6 mice with subcutaneously transplanted B16 melanoma in order to screen the optimal chemical structure for melanoma scintigraphy. Using Tl(TFA)₃ for ¹³¹I⁻ labeling, 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 (1) and N-(2-diethylaminoethyl)-3-[¹³¹I]iodo-4-methoxybenzamide (2) 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.