Synthesis of a β-Tetrapeptide Analog as a Mother Compound for the Development of Matrix Metalloproteinase-2-Imaging Agents
作者： Takahiro Mukai , Noriko Suganuma , Kenta Soejima , Junichi Sasaki , Fumihiko Yamamoto
DOI: 10.1248/CPB.56.260
关键词:
摘要: Matrix metalloproteinase-2 (MMP-2) is an attractive target for the diagnosis of cancer and atherosclerosis in nuclear imaging. A cyclic decapeptide, cCTTHWGFTLC (cCTT), has been used as mother compound development MMP-2-imaging agents with high potency selectivity. Most radiolabeled derivatives cCTT currently developed vivo studies MMP-2, however, suffer from low accumulation tissues, such tumors. For enhanced stability tissue penetration, we designed a linear beta-tetrapeptide analog, H-beta 3-Phe-beta-Ala-beta 3-Trp-beta 3-His-OH (1), to mimic cCTT. The component beta-amino acids were prepared by reduction N-protected alpha-amino acid methyl esters alcohols, followed conversion into cyanides, subsequent hydrolysis. Compound 1 was obtained these conventional solution method. In MMP-2 inhibition assay, displayed desirably significant inhibition, which comparable These findings suggest that may serve design agents.
sci-hub.se 参考文章(23)
Shigeyoshi Itohara, Masatoshi Tanioka, Hiroshi Yoshida, Hirofumi Nishimoto, Takeshi Itoh, Takayuki Yoshioka, Reduced angiogenesis and tumor progression in gelatinase A-deficient mice. Cancer Research. ,vol. 58, pp. 1048- 1051 ,(1998)
Erkki Koivunen, Wadih Arap, Heli Valtanen, Aija Rainisalo, Oula Penate Medina, Pia Heikkilä, Carmela Kantor, Carl G. Gahmberg, Tuula Salo, Yrjö T. Konttinen, Timo Sorsa, Erkki Ruoslahti, Renata Pasqualini, Tumor targeting with a selective gelatinase inhibitor Nature Biotechnology. ,vol. 17, pp. 768- 774 ,(1999) , 10.1038/11703
Amit Kumar, Stephanos Ghilagaber, Jamie Knight, Peter B. Wyatt, The homologation of histidine Tetrahedron Letters. ,vol. 43, pp. 6991- 6994 ,(2002) , 10.1016/S0040-4039(02)01587-3
Dagmar Hartung, Michael Schäfers, Shinichiro Fujimoto, Bodo Levkau, Navneet Narula, Klaus Kopka, Renu Virmani, Chris Reutelingsperger, Leo Hofstra, Frank D. Kolodgie, Artiom Petrov, Jagat Narula, Targeting of matrix metalloproteinase activation for noninvasive detection of vulnerable atherosclerotic lesions European Journal of Nuclear Medicine and Molecular Imaging. ,vol. 34, pp. 1- 8 ,(2007) , 10.1007/S00259-007-0435-0
Jennifer E. Sprague, Wen Ping Li, Kexian Liang, Samuel Achilefu, Carolyn J. Anderson, In vitro and in vivo investigation of matrix metalloproteinase expression in metastatic tumor models. Nuclear Medicine and Biology. ,vol. 33, pp. 227- 237 ,(2006) , 10.1016/J.NUCMEDBIO.2005.10.011
Shuang Liu, Radiolabeled Multimeric Cyclic RGD Peptides as Integrin αvβ3 Targeted Radiotracers for Tumor Imaging Molecular Pharmaceutics. ,vol. 3, pp. 472- 487 ,(2006) , 10.1021/MP060049X
Gilles Guichard, Stefan Abele, Dieter Seebach, Preparation of N-Fmoc-Protected β2- and β3-Amino Acids and their use as building blocks for the solid-phase synthesis of β-peptides†‡ Helvetica Chimica Acta. ,vol. 81, pp. 187- 206 ,(1998) , 10.1002/HLCA.19980810202
Karl Gademann, Thierry Kimmerlin, Daniel Hoyer, Dieter Seebach, Peptide Folding Induces High and Selective Affinity of a Linear and Small β-Peptide to the Human Somatostatin Receptor 4 Journal of Medicinal Chemistry. ,vol. 44, pp. 2460- 2468 ,(2001) , 10.1021/JM010816Q
Hirofumi Hanaoka, Takahiro Mukai, Sayo Habashita, Daigo Asano, Kazuma Ogawa, Yoshihiro Kuroda, Hiromichi Akizawa, Yasuhiko Iida, Keigo Endo, Tsuneo Saga, Hideo Saji, Chemical design of a radiolabeled gelatinase inhibitor peptide for the imaging of gelatinase activity in tumors Nuclear Medicine and Biology. ,vol. 34, pp. 503- 510 ,(2007) , 10.1016/J.NUCMEDBIO.2007.04.002
Marie-Isabel Aguilar, David Steer, Rebecca Lew, Patrick Perlmutter, A. Smith, β-amino acids: Versatile peptidomimetics Current Medicinal Chemistry. ,vol. 9, pp. 811- 822 ,(2002) , 10.2174/0929867024606759