AS1387392, a novel immunosuppressive cyclic tetrapeptide compound with inhibitory activity against mammalian histone deacetylase

Sasamura, Satoshi; Sakamoto, Kazutoshi; Takagaki, Shoji; Yamada, Toshiko; Takase, Shigehiro; Mori, Hajime; Fujii, Takashi; Hino, Motohiro; Hashimoto, Michizane

doi:10.1038/ja.2012.13

Cited by 4 publications

(4 citation statements)

References 12 publications

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“…Spatially fixed arrangements of functional moieties arouse outstanding bioactivities, especially in small cyclic peptides [ 7 , 8 , 9 , 10 , 11 , 12 ]. Nowadays several cyclic tetrapeptides that modify eukaryotic gene expression [ 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ], that interact with cellular receptors [ 11 , 21 , 22 , 23 , 24 , 25 ] or that display antimicrobial activity [ 12 , 26 , 27 , 28 , 29 , 30 ] are known.…”

Section: Introductionmentioning

confidence: 99%

Macrocyclic Tetramers—Structural Investigation of Peptide-Peptoid Hybrids

et al. 2021

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Outstanding affinity and specificity are the main characteristics of peptides, rendering them interesting compounds for basic and medicinal research. However, their biological applicability is limited due to fast proteolytic degradation. The use of mimetic peptoids overcomes this disadvantage, though they lack stereochemical information at the α-carbon. Hybrids composed of amino acids and peptoid monomers combine the unique properties of both parent classes. Rigidification of the backbone increases the affinity towards various targets. However, only little is known about the spatial structure of such constrained hybrids. The determination of the three-dimensional structure is a key step for the identification of new targets as well as the rational design of bioactive compounds. Herein, we report the synthesis and the structural elucidation of novel tetrameric macrocycles. Measurements were taken in solid and solution states with the help of X-ray scattering and NMR spectroscopy. The investigations made will help to find diverse applications for this new, promising compound class.

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Section: Introductionmentioning

confidence: 99%

Macrocyclic Tetramers—Structural Investigation of Peptide-Peptoid Hybrids

et al. 2021

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“…FERM BP‐6539) was assigned the l ‐configuration . Later on, the same strain was shown to produce the cyclotetrapeptaibiotic AS1387392, which also contains one l ‐Iva residue . The atypical, sponge‐associated marine fungus Acremonium sp.…”

Section: Introductionmentioning

confidence: 99%

Sequences of Acretocins, Peptaibiotics Containing the Rare 1‐Aminocyclopropanecarboxylic Acid, from Acremonium crotocinigenum CBS 217.70

Brückner

Fox

Degenkolb

2019

Chemistry & Biodiversity

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“…number 27082 afforded a cyclotetrapeptide AS1387392 (18), an immunosuppressant, possessing a strong inhibitory activity against mammalian HDAC and T-cell proliferation, with good oral bioavailability [29].…”

Section: Introductionmentioning

confidence: 99%

“…The peptide was synthesized and displayed antifungal and antihelmintic activity against pathogenic dermatophytes and earthworms [36,52]. Teixobactin (29) is an 11-mer peptide that contains a cyclotetradepsipeptide within its structural framework and shows potent activity against M. tuberculosis. Researchers discovered several methods to grow uncultured organisms and succeeded in growing previously unculturable bacteria named Eleftheria terrae, which produced this antibiotic.…”

Section: Introductionmentioning

confidence: 99%

Medicinal significance of naturally occurring cyclotetrapeptides

Abdalla

2016

J Nat Med

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Bioactive natural products are serendipitous drug candidates, which stimulate synthetic approaches for improving and supporting drug discovery and development. Therefore, the search for bioactive metabolites from different natural sources continues to play an important role in fashioning new medicinal agents. Several cyclic peptides were produced by organisms, such as b-defensins, gramicidin S, and tyrocidine A, and exhibited a wide range of bioactivities, such as antiviral activity against HIV-1, influenza A viruses, or antibacterial activity. Cyclic tetrapeptides are a class of natural products that were found to have a broad range of biological activities, promising pharmacokinetic properties, as well as interesting conformational dynamics and ability of slow inter-conversion to several different structures. Cyclooligopeptides, particularly medium ring-sized peptides, were obtained from marine microorganisms and exhibited a wide range of pharmacological properties, including antimicrobial and anti-dinoflagellate activities, cytotoxicity, and inhibitory activity against enzyme sortase B. Most of the naturally occurring cyclotetrapeptides are obtained from fungi. Some natural cyclic tetrapeptides were found to inhibit histone deacetylase (HDAC), which regulate the expression of genes. These compounds are very useful as cancer therapeutics. Various analogues of the natural cyclotetrapeptides were successfully synthesized to find novel lead compounds for pharmacological and biotechnological applications. Therefore, in this review, previously reported novel natural cyclotetrapeptides are briefly discussed, along with their important biological activities as drug candidates, together with their promising therapeutic properties. Moreover, their future perspective in drug discovery as potential therapeutic agents will be determined.

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AS1387392, a novel immunosuppressive cyclic tetrapeptide compound with inhibitory activity against mammalian histone deacetylase

Cited by 4 publications

References 12 publications

Macrocyclic Tetramers—Structural Investigation of Peptide-Peptoid Hybrids

Macrocyclic Tetramers—Structural Investigation of Peptide-Peptoid Hybrids

Sequences of Acretocins, Peptaibiotics Containing the Rare 1‐Aminocyclopropanecarboxylic Acid, from Acremonium crotocinigenum CBS 217.70

Medicinal significance of naturally occurring cyclotetrapeptides

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