Cycloforskamide, a Cytotoxic Macrocyclic Peptide from the Sea Slug <i>Pleurobranchus forskalii</i>

Tan, K.; Wakimoto, Toshiyuki; Takada, Kentaro; Ohtsuki, Takashi; Uchiyama, Nahoko; Goda, Yukihiro; Abe, Ikuro

doi:10.1021/np400404r

Cited by 24 publications

(17 citation statements)

References 16 publications

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“…In Indonesia, P. forskalii presents a cyclic hexapeptide instead, keenamide A (262), containing a thiazoline and an isoprene residue, which has been reported active against four cancer cell lines (P388, A549, MEL20, and HT29) with IC 50 values of 2.5-8 µM [611,612]. In Japan, P. forskalii contains a macrocyclic dodecapeptide, cycloforskamide (263), contaning three thiazoline heterocycles [612]. Cycloforskamide ( 263) displays an IC 50 value of 5.8 µM against murine P388 leukemia cells [387].…”

Section: Pleurobranchoideamentioning

confidence: 99%

Bioactive Compounds from Marine Heterobranchs

Ávila

Angulo‐Preckler

2020

Marine Drugs

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The natural products of heterobranch molluscs display a huge variability both in structure and in their bioactivity. Despite the considerable lack of information, it can be observed from the recent literature that this group of animals possesses an astonishing arsenal of molecules from different origins that provide the molluscs with potent chemicals that are ecologically and pharmacologically relevant. In this review, we analyze the bioactivity of more than 450 compounds from ca. 400 species of heterobranch molluscs that are useful for the snails to protect themselves in different ways and/or that may be useful to us because of their pharmacological activities. Their ecological activities include predator avoidance, toxicity, antimicrobials, antifouling, trail-following and alarm pheromones, sunscreens and UV protection, tissue regeneration, and others. The most studied ecological activity is predation avoidance, followed by toxicity. Their pharmacological activities consist of cytotoxicity and antitumoral activity; antibiotic, antiparasitic, antiviral, and anti-inflammatory activity; and activity against neurodegenerative diseases and others. The most studied pharmacological activities are cytotoxicity and anticancer activities, followed by antibiotic activity. Overall, it can be observed that heterobranch molluscs are extremely interesting in regard to the study of marine natural products in terms of both chemical ecology and biotechnology studies, providing many leads for further detailed research in these fields in the near future.

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Section: Pleurobranchoideamentioning

confidence: 99%

Bioactive Compounds from Marine Heterobranchs

Ávila

Angulo‐Preckler

2020

Marine Drugs

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“…Other sources of proline-rich cyclooligopeptides are marine tunicates, like compound ascidian Didemnum molle [40], Ishigaki Island sea slug Pleurobranchus forskalii [41], Fijian ascidian Eudistoma sp. [42], Caribbean tunicate Trididemnum solidum [43], unidentified Brazilian ascidian (family Didemnidae) [44], Mediterranean ascidian Aplidium albicans [45], cyanobacteria like Papua New Guinea cyanobacterium Lyngbya semiplena [46], Red Sea cyanobacterium Moorea producens [47], Florida Everglades cyanobacterium Lyngbya sp.…”

Section: Introductionmentioning

confidence: 99%

Natural Proline-Rich Cyclopolypeptides from Marine Organisms: Chemistry, Synthetic Methodologies and Biological Status

et al. 2016

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Peptides have gained increased interest as therapeutics during recent years. More than 60 peptide drugs have reached the market for the benefit of patients and several hundreds of novel therapeutic peptides are in preclinical and clinical development. The key contributor to this success is the potent and specific, yet safe, mode of action of peptides. Among the wide range of biologically-active peptides, naturally-occurring marine-derived cyclopolypeptides exhibit a broad range of unusual and potent pharmacological activities. Because of their size and complexity, proline-rich cyclic peptides (PRCPs) occupy a crucial chemical space in drug discovery that may provide useful scaffolds for modulating more challenging biological targets, such as protein-protein interactions and allosteric binding sites. Diverse pharmacological activities of natural cyclic peptides from marine sponges, tunicates and cyanobacteria have encouraged efforts to develop cyclic peptides with well-known synthetic methods, including solid-phase and solution-phase techniques of peptide synthesis. The present review highlights the natural resources, unique structural features and the most relevant biological properties of proline-rich peptides of marine-origin, focusing on the potential therapeutic role that the PRCPs may play as a promising source of new peptide-based novel drugs.

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“…This compound showed cytotoxic effect against P388 cells with an IC 50 value of 5.8 µM. In addition, from an ecological perspective, cycloforskamide is presumed to chelate toxic metals and plays a detoxification role [100].…”

Section: Anticancer Cyclopeptides Derived From Ascidians/tunicatesmentioning

confidence: 99%

Natural Cyclopeptides as Anticancer Agents in the Last 20 Years

Zhang

Xia

Zhang

2021

IJMS

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Cyclopeptides or cyclic peptides are polypeptides formed by ring closing of terminal amino acids. A large number of natural cyclopeptides have been reported to be highly effective against different cancer cells, some of which are renowned for their clinical uses. Compared to linear peptides, cyclopeptides have absolute advantages of structural rigidity, biochemical stability, binding affinity as well as membrane permeability, which contribute greatly to their anticancer potency. Therefore, the discovery and development of natural cyclopeptides as anticancer agents remains attractive to academic researchers and pharmaceutical companies. Herein, we provide an overview of anticancer cyclopeptides that were discovered in the past 20 years. The present review mainly focuses on the anticancer efficacies, mechanisms of action and chemical structures of cyclopeptides with natural origins. Additionally, studies of the structure–activity relationship, total synthetic strategies as well as bioactivities of natural cyclopeptides are also included in this article. In conclusion, due to their characteristic structural features, natural cyclopeptides have great potential to be developed as anticancer agents. Indeed, they can also serve as excellent scaffolds for the synthesis of novel derivatives for combating cancerous pathologies.

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Cycloforskamide, a Cytotoxic Macrocyclic Peptide from the Sea Slug Pleurobranchus forskalii

Cited by 24 publications

References 16 publications

Bioactive Compounds from Marine Heterobranchs

Bioactive Compounds from Marine Heterobranchs

Natural Proline-Rich Cyclopolypeptides from Marine Organisms: Chemistry, Synthetic Methodologies and Biological Status

Natural Cyclopeptides as Anticancer Agents in the Last 20 Years

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