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Pregled bibliografske jedinice broj: 212391

Tumor-Cell Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis and In Vitro Antitumor Activity


Horvat, Štefica; Mlinarić-Majerski, Kata; Glavaš-Obrovac, Ljubica; Jakas, Andreja; Veljković, Jelena; Marczi, Saška; Kragol, Goran; Roščić, Maja; Matković, Marija; Milostić-Srb, Andrea
Tumor-Cell Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis and In Vitro Antitumor Activity // Journal of medicinal chemistry, 49 (2006), 3136-3142 (međunarodna recenzija, članak, znanstveni)


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Naslov
Tumor-Cell Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis and In Vitro Antitumor Activity

Autori
Horvat, Štefica ; Mlinarić-Majerski, Kata ; Glavaš-Obrovac, Ljubica ; Jakas, Andreja ; Veljković, Jelena ; Marczi, Saška ; Kragol, Goran ; Roščić, Maja ; Matković, Marija ; Milostić-Srb, Andrea

Izvornik
Journal of medicinal chemistry (0022-2623) 49 (2006); 3136-3142

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
adamantane; cytotoxicity; in vitro; methionine-enkephalin; opioid growth factor; OGF; peptide; unnatural amino acid

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekti:
0127111
0098052
0098054

Ustanove:
Institut "Ruđer Bošković", Zagreb


Citiraj ovu publikaciju

Horvat, Štefica; Mlinarić-Majerski, Kata; Glavaš-Obrovac, Ljubica; Jakas, Andreja; Veljković, Jelena; Marczi, Saška; Kragol, Goran; Roščić, Maja; Matković, Marija; Milostić-Srb, Andrea
Tumor-Cell Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis and In Vitro Antitumor Activity // Journal of medicinal chemistry, 49 (2006), 3136-3142 (međunarodna recenzija, članak, znanstveni)
Horvat, Š., Mlinarić-Majerski, K., Glavaš-Obrovac, L., Jakas, A., Veljković, J., Marczi, S., Kragol, G., Roščić, M., Matković, M. & Milostić-Srb, A. (2006) Tumor-Cell Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis and In Vitro Antitumor Activity. Journal of medicinal chemistry, 49, 3136-3142.
@article{article, year = {2006}, pages = {3136-3142}, keywords = {adamantane, cytotoxicity, in vitro, methionine-enkephalin, opioid growth factor, OGF, peptide, unnatural amino acid}, journal = {Journal of medicinal chemistry}, volume = {49}, issn = {0022-2623}, title = {Tumor-Cell Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis and In Vitro Antitumor Activity}, keyword = {adamantane, cytotoxicity, in vitro, methionine-enkephalin, opioid growth factor, OGF, peptide, unnatural amino acid} }
@article{article, year = {2006}, pages = {3136-3142}, keywords = {adamantane, cytotoxicity, in vitro, methionine-enkephalin, opioid growth factor, OGF, peptide, unnatural amino acid}, journal = {Journal of medicinal chemistry}, volume = {49}, issn = {0022-2623}, title = {Tumor-Cell Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids: Design, Synthesis and In Vitro Antitumor Activity}, keyword = {adamantane, cytotoxicity, in vitro, methionine-enkephalin, opioid growth factor, OGF, peptide, unnatural amino acid} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE





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