Diastereomer-Specific Effects of Double-Stranded Peptides Conjugated with-L-Tyr-L-Phe-or-L-Tyr-D-Phe-Residues on Tyrosine : Phosphorylation and Inhibition of src^<ts>NRK, A431, MCF-7, and DU145 Cell Growth
スポンサーリンク
概要
- 論文の詳細を見る
The interaction between growth inhibition and chirality, especially of diastereomers, has an important modifying effect on cancer cell proliferation. Previously, we have reported on the design, synthesis, and chemical properties of a series of novel, double-stranded peptides, (y-AA-x-AA)_2-(CH_2)_<12>, with-y-AA-x-AA- and -z-AA-y-AA-x-AA-sequences conjugated to the spacer. Here, we extend those results by showing that (D-, L-) and (L-, D-) diastereomers are more potent inhibitors of tyrosine phosphorylation than (L-, L-). Although the replacement of the L-Phe-L-Phe sequence with L-Tyr-L-Phe produces a less active inhibitor, the double-stranded peptide conjugated with L-Tyr-D-Phe is more active than that conjugated with L-Tyr-L-Phe. In addition, we show that SDS-PAGE gel profiles of tyrosine phosphorylation following treatment with bis (y-Tyr-x-Phe)-N, N-dodecane-1, 12-diamine appear very similar to profiles of tyrosine phosphorylation following treatment with an analog of the tyrosine kinase inhibitor, erbstatin. Moreover, the level of autophosphorylation of the epidermal growth factor receptor kinase domain (EGFRKD) treated with bis (L-Tyr-D-Phe)-N, N-dodecane-1, 12-diamine was lower than that seen following treatment with bis (L-Phe-D-Phe)-N, N-dodecane-1, 12-diamine. These data provide new insights for the control of cancer cell proliferation through drug designs which replace the less active-L-Phe-L-Phe-(and-D-Phe-L-Phe-) with the more active-L-Tyr-L-Phe-(and-L-Tyr-D-Phe-) sequence.
- 公益社団法人日本薬学会の論文
- 2007-11-01
著者
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Kobayashi Shigeki
Division of Cardiology, Department of Medicine and Clinical Science, Yamaguchi University Graduate S
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Kobayashi S
Eisai Research Institute Of Boston Inc.
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Kobayashi Shoichi
Laboratory Of Food And Health Science Department Of Agro-bioscience Faculty Of Agriculture Iwate Uni
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Kobayashi Shigeki
Division Of Cardiology Department Of Medicine And Clinical Science Yamaguchi University Graduate Sch
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Kobayashi Shigeki
Department Of Analytical Chemistry Of Medicines Showa Phamaceutical University
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Kobayashi Shigeki
Department Of Analytical Chemistry Of Medicines Showa Pharmaceutical University
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ATUCHI Nahomi
Division of Analytical Chemistry of Medicines, Showa Pharmaceutical University
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WAKAMATSU Hidetaka
Division of Analytical Chemistry of Medicines, Showa Pharmaceutical University
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HATTORI Mayuko
Division of Analytical Chemistry of Medicines, Showa Pharmaceutical University
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KAWADA Ayumi
Division of Analytical Chemistry of Medicines, Showa Pharmaceutical University
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ASANO Kouji
Department of Urology, Jikei University School of Medicine
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WAKAMATSU Hidetaka
Department of Analytical Chemistry of Medicines, Showa Pharmaceutical University
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ATUCHI Nahomi
Department of Analytical Chemistry of Medicines, Showa Pharmaceutical University
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KAWADA Ayumi
Department of Analytical Chemistry of Medicines, Showa Pharmaceutical University
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HATTORI Mayuko
Department of Analytical Chemistry of Medicines, Showa Pharmaceutical University
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Kobayashi Shigeki
Div. Of Analytical Chemistry Of Medicines Showa Pharmaceutical Univ.
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Asano Kouji
Department Of Electrical Engineering Tohoku University
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Asano Kouji
Department Of Urology Jikei University School Of Medicine
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Kawada Ayumi
Department Of Analytical Chemistry Of Medicines Showa Pharmaceutical University
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Atuchi Nahomi
Department Of Analytical Chemistry Of Medicines Showa Pharmaceutical University
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Hattori Mayuko
Department Of Analytical Chemistry Of Medicines Showa Pharmaceutical University
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Kobayashi Shigeki
Division Of Analytical Chemistry Of Medicines Showa Pharmaceutical University
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Wakamatsu Hidetaka
Department Of Analytical Chemistry Of Medicines Showa Pharmaceutical University
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