Effect of carboxylation of N-terminal phenylalanine of 111In- DTPA (diethylenetriaminepentaacetic acid)-octreotide on accumulation of radioactivity in kidney

Hiromichi Akizawa; Hirokazu Takimoto; Madoka Saito; Akimasa Iwado; Masaki Mifune; Yutaka Saito; Tomoya Uehara; Yasushi Arano; Takahiro Mukai; Hirofumi Hanaoka; Hideo Saji

doi:10.1248/bpb.27.271

Effect of carboxylation of N-terminal phenylalanine of ¹¹¹In- DTPA (diethylenetriaminepentaacetic acid)-octreotide on accumulation of radioactivity in kidney

Hiromichi Akizawa, Hirokazu Takimoto, Madoka Saito, Akimasa Iwado, Masaki Mifune, Yutaka Saito, Tomoya Uehara, Yasushi Arano, Takahiro Mukai, Hirofumi Hanaoka, Hideo Saji

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

For purpose of reducing renal accumulation of radioactivity of a known radiopharmaceutical agent, i.e., ¹¹¹In-DTPA (diethylenetriaminepentaacetic acid)-D-Phe¹-octreotide, a derivative in which p-carboxy-L-phenylalanine is substituted for D-Phe¹ was synthesized. Biodistribution study of the resultant compound having carboxy-substituted L-Phe¹ revealed that the renal accumulation was significantly lower than that of control compound having unsubstituted L-Phe¹, demonstrating that the presence of negative charge on the N-terminal amino acid of octreotide is effective to reduce the renal accumulation. This effect can be attributed to the reduction of lipophilicity and also the repulsive force arisen from the negative charge of renal brush border membrane.

Original language	English
Pages (from-to)	271-272
Number of pages	2
Journal	Biological and Pharmaceutical Bulletin
Volume	27
Issue number	2
DOIs	https://doi.org/10.1248/bpb.27.271
Publication status	Published - Feb 2004

Keywords

In-DTPA-octreotide
Renal accumulation
p-carboxy-phenylalanine

ASJC Scopus subject areas

Pharmacology
Pharmaceutical Science

Access to Document

10.1248/bpb.27.271

Cite this

Akizawa, H., Takimoto, H., Saito, M., Iwado, A., Mifune, M., Saito, Y., Uehara, T., Arano, Y., Mukai, T., Hanaoka, H., & Saji, H. (2004). Effect of carboxylation of N-terminal phenylalanine of ¹¹¹In- DTPA (diethylenetriaminepentaacetic acid)-octreotide on accumulation of radioactivity in kidney. Biological and Pharmaceutical Bulletin, 27(2), 271-272. https://doi.org/10.1248/bpb.27.271

Effect of carboxylation of N-terminal phenylalanine of ¹¹¹In- DTPA (diethylenetriaminepentaacetic acid)-octreotide on accumulation of radioactivity in kidney. / Akizawa, Hiromichi; Takimoto, Hirokazu; Saito, Madoka et al.
In: Biological and Pharmaceutical Bulletin, Vol. 27, No. 2, 02.2004, p. 271-272.

Research output: Contribution to journal › Article › peer-review

Akizawa, H, Takimoto, H, Saito, M, Iwado, A, Mifune, M, Saito, Y, Uehara, T, Arano, Y, Mukai, T, Hanaoka, H & Saji, H 2004, 'Effect of carboxylation of N-terminal phenylalanine of ¹¹¹In- DTPA (diethylenetriaminepentaacetic acid)-octreotide on accumulation of radioactivity in kidney', Biological and Pharmaceutical Bulletin, vol. 27, no. 2, pp. 271-272. https://doi.org/10.1248/bpb.27.271

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abstract = "For purpose of reducing renal accumulation of radioactivity of a known radiopharmaceutical agent, i.e., 111In-DTPA (diethylenetriaminepentaacetic acid)-D-Phe1-octreotide, a derivative in which p-carboxy-L-phenylalanine is substituted for D-Phe1 was synthesized. Biodistribution study of the resultant compound having carboxy-substituted L-Phe1 revealed that the renal accumulation was significantly lower than that of control compound having unsubstituted L-Phe1, demonstrating that the presence of negative charge on the N-terminal amino acid of octreotide is effective to reduce the renal accumulation. This effect can be attributed to the reduction of lipophilicity and also the repulsive force arisen from the negative charge of renal brush border membrane.",

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