Cyanopeptolins with Trypsin and Chymotrypsin Inhibitory Activity from the Cyanobacterium Nostoc edaphicum CCNP1411

Hanna Mazur-Marzec , Anna Fidor , Marta Cegłowska , Ewa Wieczerzak , Magdalena Kropidłowska , Marie Goua , Jenny Macaskill , Christine Edwards


Cyanopeptolins (CPs) are one of the most frequently occurring cyanobacterial peptides, many of which are inhibitors of serine proteases. Some CP variants are also acutely toxic to aquatic organisms, especially small crustaceans. In this study, thirteen CPs, including twelve new variants, were detected in the cyanobacterium Nostoc edaphicum CCNP1411 isolated from the Gulf of Gdańsk (southern Baltic Sea). Structural elucidation was performed by tandem mass spectrometry with verification by NMR for CP962 and CP985. Trypsin and chymotrypsin inhibition assays confirmed the significance of the residue adjacent to 3-amino-6-hydroxy-2-piperidone (Ahp) for the activity of the peptides. Arginine-containing CPs (CPs-Arg2) inhibited trypsin at low IC50 values (0.24–0.26 µM) and showed mild activity against chymotrypsin (IC50 3.1–3.8 µM), while tyrosine-containing CPs (CPs-Tyr2) were selectively and potently active against chymotrypsin (IC50 0.26 µM). No degradation of the peptides was observed during the enzyme assays. Neither of the CPs were active against thrombin, elastase or protein phosphatase 1. Two CPs (CP962 and CP985) had no cytotoxic effects on MCF-7 breast cancer cells. Strong and selective activity of the new cyanopeptolin variants makes them potential candidates for the development of drugs against metabolic disorders and other diseases.
Author Hanna Mazur-Marzec (FOG/IO/DMarB)
Hanna Mazur-Marzec,,
- Division of Marine Biotechnology
, Anna Fidor (FOG/IO/DMarB)
Anna Fidor,,
- Division of Marine Biotechnology
, Marta Cegłowska
Marta Cegłowska,,
, Ewa Wieczerzak (FCh/DBCh/LMCh)
Ewa Wieczerzak,,
- Laboratory of Medical Chemistry
, Magdalena Kropidłowska (FCh/DBCh/LMCh)
Magdalena Kropidłowska ,,
- Laboratory of Medical Chemistry
, Marie Goua
Marie Goua,,
, Jenny Macaskill
Jenny Macaskill,,
, Christine Edwards
Christine Edwards,,
Journal seriesMarine Drugs, ISSN 1660-3397, (A 40 pkt)
Issue year2018
Publication size in sheets0.90
Article number220
Keywords in Englishcyanobacteria, Nostoc, cyanopeptolins, protease inhibitors
ASJC Classification3002 Drug Discovery
Languageen angielski
LicenseJournal (articles only); published final; Uznanie Autorstwa (CC-BY); with publication
Score (nominal)40
Score sourcejournalList
ScoreMinisterial score = 40.0, 04-02-2020, ArticleFromJournal
Publication indicators WoS Citations = 0.000; Scopus SNIP (Source Normalised Impact per Paper): 2017 = 1.537; WoS Impact Factor: 2018 = 3.772 (2) - 2018=4.446 (5)
Citation count*6 (2020-06-29)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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