Tumor-Cell Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis and In Vitro Antitumor Activity (CROSBI ID 116985)
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Horvat, Štefica ; Mlinarić-Majerski, Kata ; Glavaš-Obrovac, Ljubica ; Jakas, Andreja ; Veljković, Jelena ; Marczi, Saška ; Kragol, Goran ; Roščić, Maja ; Matković, Marija ; Milostić-Srb, Andrea
engleski
Tumor-Cell Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis and In Vitro Antitumor Activity
A series of new peptides (8-25) containing different unnatural amino acids of the adamantane type (1-6), was synthesized. Possible cytotoxic activity on human cervical adenocarcinoma (HeLa), larynx carcinoma (HEp-2), colon carcinomas (HT-29, Caco-2), poorly differentiated cells from lymph node metastasis of colon carcinoma (SW-620), mammary gland adenocarcinoma (MCF-7), and melanoma (HBL) cells were tested using the MTT assay. The results were compared with the effect of methionine-enkephalin (Tyr-Gly-Gly-Phe-Met, OGF), and its shorter N-terminal fragments. Peptide analogues containing dialkylated glycine (Aaa1, 1) or alkylated glycine (Aaa2, 2) amino acid residues showed antitumor activity against melanoma, larynx carcinoma, colon carcinomas, and colon metastasis cell lines in vitro. The pentapeptide Tyr-(R, S)-Aaa2-Gly-Phe-Met (18) was the most effective analogue especially against the most antitumor drug-resistant cell lines HEp-2 and SW-620. Apoptosis as a mode of cell death was confirmed in these tumor cells after exposure to pentapeptide 18.
adamantane; cytotoxicity; in vitro; methionine-enkephalin; opioid growth factor; OGF; peptide; unnatural amino acid
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Povezanost rada
Kemija, Temeljne medicinske znanosti, Biologija