Synthetic studies on cyclic octapeptides: Yunnanin F and Hymenistatin

Poojary, Boja; Belagali, S. L.

doi:10.1016/j.ejmech.2004.11.013

Cited by 13 publications

(8 citation statements)

References 9 publications

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“…The literature is enriched with reports explaining the synthesis of euryjanicin A [108], delavayin C [109], cherimolacyclopeptide G [110], psammosilenin A [111], hymenamide E [112], stylisin 1 [113], stylisin 2 [114], hymenistatin and yunnanin F [115], pseudostellarin B [116], segetalin E [117], rolloamide B [118] and pseudostellarin G [119] using the solution-phase method utilizing different carbodiimides as coupling agents, TEA/NMM as the base and the synthesis of euryjanicin B [120], mollamide [121], met-cherimolacyclopeptide B [122], axinellin A [123], phakellistatin 7 [124], phakellistatin 12 [125], petriellin A [126], hymenamide C [127], gombamide A [128] and scleritodermin A [129] by the solid-phase method of peptide synthesis. Solid-phase peptide synthesis (SPPS) results in high yields of pure products and works more quickly than classical synthesis, i.e., liquid-phase peptide synthesis (LPPS).…”

Section: Chemistrymentioning

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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Section: Chemistrymentioning

confidence: 99%

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

et al. 2016

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“…Three other yunnanins, named yunnanins D, E, and F, were isolated from Stellaria yunnanensis, and their structures were confirmed by spectroscopic and chemical analysis ( 41 ). Later, in 2005, the total synthesis of yunnanin F was reported using a disconnection approach ( 42 ). By screening for antimicrobial and pharmacological activities, yunnanin F showed moderate-to-good inhibitory activity against the growth of bacterial cells and weak activity against fungal cells ( 42 ).…”

Section: Yunnaninsmentioning

confidence: 99%

“…Later, in 2005, the total synthesis of yunnanin F was reported using a disconnection approach ( 42 ). By screening for antimicrobial and pharmacological activities, yunnanin F showed moderate-to-good inhibitory activity against the growth of bacterial cells and weak activity against fungal cells ( 42 ). Meanwhile, this cyclopeptide demonstrated a good anthelmintic activity against earthworms ( 42 ).…”

Section: Yunnaninsmentioning

confidence: 99%

“…By screening for antimicrobial and pharmacological activities, yunnanin F showed moderate-to-good inhibitory activity against the growth of bacterial cells and weak activity against fungal cells ( 42 ). Meanwhile, this cyclopeptide demonstrated a good anthelmintic activity against earthworms ( 42 ). From the point of pharmacological activity, yunnanin F produced moderate anti-inflammatory activity ( 42 ).…”

Section: Yunnaninsmentioning

confidence: 99%

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Cancer Treatment by Caryophyllaceae-Type Cyclopeptides

et al. 2021

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Cancer is one of the leading diseases, which, in the most cases, ends with death and, thus, continues to be a major concern in human beings worldwide. The conventional anticancer agents used in the clinic often face resistance among many cancer diseases. Moreover, heavy financial costs preclude patients from continuing treatment. Bioactive peptides, active in several diverse areas against man’s health problems, such as infection, pain, hypertension, and so on, show the potential to be effective in cancer treatment and may offer promise as better candidates for combating cancer. Cyclopeptides, of natural or synthetic origin, have several advantages over other drug molecules with low toxicity and low immunogenicity, and they are easily amenable to several changes in their sequences. Given their many demanded homologues, they have created new hope of discovering better compounds with desired properties in the field of challenging cancer diseases. Caryophyllaceae-type cyclopeptides show several biological activities, including cancer cytotoxicity. These cyclopeptides have been discovered in several plant families but mainly are from the Caryophyllaceae family. In this review, a summary of biological activities found for these cyclopeptides is given; the focus is on the anticancer findings of these peptides. Among these cyclopeptides, information about Dianthins (including Longicalycinin A), isolated from different species of Caryophyllaceae, as well as their synthetic analogues is detailed. Finally, by comparing their structures and cytotoxic activities, finding the common figures of these kinds of cyclopeptides as well as their possible future place in the clinic for cancer treatment is put forward.

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“…The in vitro trial for anthelmintic activity was carried out against earthworm Pontoscotex corethruses (ICARBC 408) species [24]. The test compound suspensions were prepared by triturating the newly synthesised compounds with 0.5% Tween 80 and distilled water.…”

Section: Anthelmintic Activitymentioning

confidence: 99%