Axinellins A and B: New Proline-Containing Antiproliferative Cyclopeptides from the Vanuatu Sponge Axinella carteri

Natural Cyclopeptides as Anticancer Agents in the Last 20 Years

“…The marine sponge Axinella carteri collected near Vanuatu islands yielded two proline-containing cyclopeptides, which were called axinellins A ( 41 ) and B ( 42 ). Both compounds were found to display moderate cytotoxicity against non-small lung cancer cells (NSLC-N6) with IC 50 values of 16.7 and 29.8 µM, respectively [ 76 ]. The first synthesis of axinellin A was achieved shortly after its discovery.…”

One-Pot Cyclization and Cleavage of Peptides with N-Terminal Cysteine via the N,S-Acyl Shift of the N-2-[Thioethyl]glycine Residue

“…The corresponding LC-UV-MS data are presented in SI 6.1 . The next investigated peptide was the cysteine analog of axinellin A ( 2 ), a cytotoxic peptide isolated from marine sponges 33 ( Figure 1 ). Here we report the data for the synthesis with MPAA in the TEAB buffer medium (procedure C) that yielded 55% of 2 .…”

Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology

“…Wainunuamide was previously reported from the cyanobacterium, Oscillatoria agardhii , and was found to be weakly cytotoxic against K562 leukemia cancer and A2780 ovarian tumor cell-lines at ID 50 values of 18.36 and 19.15 μg/mL, respectively [88]. Axinellins A and B are bioactive cyclopeptides that were isolated from Axinella carteri [89], while axinellins B and C are cyclic octapeptides that were isolated from Stylotella aurantium . Axinellins A and B exhibited moderate antitumor activity against NSCLC-N6 human bronchopulmonary non-small cell lung carcinoma cell-line at IC 50 values of 3.0 and 7.3 μg/mL, respectively [89].…”

“…Axinellins A and B are bioactive cyclopeptides that were isolated from Axinella carteri [89], while axinellins B and C are cyclic octapeptides that were isolated from Stylotella aurantium . Axinellins A and B exhibited moderate antitumor activity against NSCLC-N6 human bronchopulmonary non-small cell lung carcinoma cell-line at IC 50 values of 3.0 and 7.3 μg/mL, respectively [89]. Axinellin C showed weak cytotoxicity against K562 leukemia cancer and A2780 ovarian tumor cell-lines at ID 50 values of 4.46 and 13.17 μg/mL, respectively [90].…”