Synthesis, characterization and biological evaluation of cyclomontanin D

Dahiya, Rajiv

doi:10.5897/ajpp10.384

Cited by 21 publications

(16 citation statements)

References 23 publications

(17 reference statements)

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“…Structures of diverse proline-rich cyclopeptides from marine tunicates and cyanobacteria are tabulated in Figure 2. Besides this, proline-containing cyclooligopeptides are also obtained from roots, stems, barks, seeds, fruit peels of higher plants, as well as from bacteria and fungi [53,54,55,56,57,58,59,60,61,62,63,64,65,66]. …”

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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Section: Introductionmentioning

confidence: 99%

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

et al. 2016

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“…In the pharmaceutical industry, identification of pseudopolymorphs of APIs during their early stage development is critical (Byrn et al, 1995;Starbuck et al, 2002;Dahiya and Gautam, 2011;Fan and Luo, 2011;Ding et al, 2011). In addition, the study on the solventmediated transformation between pseudopolymorphs is highly important as well.…”

Section: Introductionmentioning

confidence: 99%

Characterization and pseudopolymorphism of l-phenylalanine anhydrous and monohydrate forms

Lü¹,

Wang²,

Li³

et al. 2012

Afr. J. Pharm. Pharmacol.

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In this work, the preformulation study on the solid state characterization for the anhydrous form and the monohydrate form of L-phenylalanine has been initially conducted by the use of powder X-ray diffraction (PXRD), Fourier transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and microscopy. Meanwhile, the solubility of both forms and the transformation kinetics from anhydrous form to monohydrate form in different water/acetone mixtures were studied as well. The transformation rate can be prohibited by increasing temperature and reducing water content in the solvent mixtures. These results will contribute to a better understanding of drugs' pseudopolymorphism for pharmaceutical industry.

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“…Keeping in view the broad range of pharmacological activities possessed by natural cyclopolypeptides [24,25], including the biological potential of other stylissamides (e.g., inhibitory activity towards protein translation/synthesis by Stylissamide A [26], and inhibitory activity against migration of HeLa cells by Stylissamide X [27]), the present investigation was directed toward the synthesis and structure elucidation of stylissamide G by using a solution-phase technique to obtain a natural cyclooligopeptide in the quantitative yield in the laboratory. This study was in continuation of the efforts of our research group for the total synthesis of natural bioactive cyclic peptides of marine and plant origin [28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53]. Keeping in mind characteristic pattern of ‘Pro’ and ‘Phe’ units in its structure, the marine sponge tissue-derived cyclopolypeptide was further subjected to antibacterial, antifungal and anthelmintic screening.…”

Section: Introductionmentioning

confidence: 99%

First Total Synthesis and Biological Screening of a Proline-Rich Cyclopeptide from a Caribbean Marine Sponge

et al. 2016

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A natural heptacyclopeptide, stylissamide G (7), previously isolated from the Bahamian marine sponge Stylissa caribica from the Caribbean Sea, was synthesized via coupling of the tetrapeptide l-phenylalanyl-l-prolyl-l-phenylalanyl-l-proline methyl ester with the tripeptide Boc-l-leucyl-l-isoleucyl-l-proline, followed by cyclization of the linear heptapeptide fragment. The structure of the synthesized cyclooligopeptide was confirmed using quantitative elemental analysis, FT-IR, 1H NMR, 13C NMR and mass spectrometry. Results of pharmacological activity studies indicated that the newly synthesized cycloheptapeptide displayed good anthelmintic potential against Megascoplex konkanensis, Pontoscotex corethruses and Eudrilus eugeniea at 2 mg/mL and in addition, potent antifungal activity against pathogenic Candida albicans and dermatophytes Trichophyton mentagrophytes and Microsporum audouinii at a concentration of 6 μg/mL.

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Synthesis, characterization and biological evaluation of cyclomontanin D

Cited by 21 publications

References 23 publications

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

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

Characterization and pseudopolymorphism of l-phenylalanine anhydrous and monohydrate forms

First Total Synthesis and Biological Screening of a Proline-Rich Cyclopeptide from a Caribbean Marine Sponge

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