Heterocytous cyanobacteria are among the most prolific sources of bioactive secondary metabolites, including anabaenopeptins (APTs). A terrestrial filamentous Brasilonema sp. CT11 collected in Costa Rica bamboo forest as a black mat, was studied using a multidisciplinary approach: genome mining and HPLC-HRMS/MS coupled with bioinformatic analyses. Herein, we report the nearly complete genome consisting of 8.79 Mbp with a GC content of 42.4%. Moreover, we report on three novel tryptophan-containing APTs; anabaenopeptin 788 (1), anabaenopeptin 802 (2), and anabaenopeptin 816 (3). Furthermore, the structure of two homologues, i.e., anabaenopeptin 802 (2a) and anabaenopeptin 802 (2b), was determined by spectroscopic analysis (NMR and MS). Both compounds were shown to exert weak to moderate antiproliferative activity against HeLa cell lines. This study also provides the unique and diverse potential of biosynthetic gene clusters and an assessment of the predicted chemical space yet to be discovered from this genus.
- MeSH
- Peptides, Cyclic * chemistry genetics isolation & purification pharmacology MeSH
- HeLa Cells MeSH
- Mass Spectrometry MeSH
- Humans MeSH
- Nuclear Magnetic Resonance, Biomolecular MeSH
- Cell Proliferation drug effects MeSH
- Cyanobacteria * chemistry genetics MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
The peptide named codesane (COD), consisting of 18 amino acid residues and isolated from the venom of wild bee Colletes daviesanus (Hymenoptera : Colletidae), falls into the category of cationic α-helical amphipathic antimicrobial peptides. In our investigations, synthetic COD exhibited antimicrobial activity against Gram-positive and Gram-negative bacteria and Candida albicans but also noticeable hemolytic activity. COD and its analogs (collectively referred to as CODs) were studied for the mechanism of their action. The interaction of CODs with liposomes led to significant leakage of calcein entrapped in bacterial membrane-mimicking large unilamellar vesicles made preferentially from anionic phospholipids while no calcein leakage was observed from zwitterionic liposomes mimicking membranes of erythrocytes. The preference of CODs for anionic phospholipids was also established by the blue shift in the tryptophan emission spectra maxima when the interactions of tryptophan-containing COD analogs with liposomes were examined. Those results were in agreement with the antimicrobial and hemolytic activities of CODs. Moreover, we found that the studied peptides permeated both the outer and inner cytoplasmic membranes of Escherichia coli. This was determined by measuring changes in the fluorescence of probe N-phenyl-1-naphthylamine and detecting cytoplasmic β-galactosidase released during the interaction of peptides with E. coli cells. Transmission electron microscopy revealed that treatment of E. coli with one of the COD analogs caused leakage of bacterial content mainly from the septal areas of the cells.
- MeSH
- Anti-Bacterial Agents chemical synthesis isolation & purification pharmacology MeSH
- Escherichia coli drug effects metabolism ultrastructure MeSH
- Fluorescence MeSH
- Phospholipids metabolism MeSH
- Hemolysis drug effects MeSH
- Hydrophobic and Hydrophilic Interactions MeSH
- Antimicrobial Cationic Peptides genetics isolation & purification pharmacology MeSH
- Liposomes metabolism MeSH
- Molecular Sequence Data MeSH
- Cell Membrane Permeability drug effects MeSH
- Drug Design MeSH
- Protein Structure, Secondary MeSH
- Amino Acid Sequence MeSH
- Microscopy, Electron, Transmission MeSH
- Tryptophan chemistry MeSH
- Bee Venoms chemistry genetics isolation & purification pharmacology MeSH
- Bees genetics MeSH
- Animals MeSH
- Check Tag
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- MeSH
- Adiponectin analysis physiology MeSH
- Diphosphonates therapeutic use MeSH
- Estrogen Replacement Therapy MeSH
- Ghrelin analysis physiology MeSH
- Pituitary Hormone-Releasing Hormones analysis physiology MeSH
- Insulin-Like Growth Factor I therapeutic use MeSH
- Drug Therapy, Combination MeSH
- Bone and Bones * metabolism MeSH
- Leptin analysis MeSH
- Humans MeSH
- Anorexia Nervosa * physiopathology MeSH
- Neuroendocrine Cells physiology MeSH
- Osteocalcin analysis MeSH
- Bone Demineralization, Pathologic drug therapy MeSH
- Peptide YY analysis physiology MeSH
- Malnutrition * physiopathology MeSH
- PPAR gamma physiology MeSH
- Bone Remodeling physiology MeSH
- Bone Resorption * MeSH
- Vitamin D therapeutic use MeSH
- Check Tag
- Humans MeSH
... aromatic and heterocyclic amino acids group 20 -- 1.5.1 Phenylalanine and tyrosine 20 -- 1.5.2 Tryptophan ... ... Cyclopentenylglycine 42 -- 1.7.4 Hydroxyamino acids 43 -- 1.7.4.1 Dihydroxyphenylalanine 43 -- 1.7.5 Sulfur-containing ... ... -- 1.8.2.1 Aldehydes 62 -- 1.8.2.2 Alcohols 63 -- 1.8.3 Other compounds 65 -- References 66 -- 2 PEPTIDES ...
1st ed. xii, 497 s. : il. ; 24 cm
- MeSH
- Biochemical Phenomena ethics drug effects radiation effects MeSH
- Chemistry MeSH
- Food MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Monograph MeSH
- Conspectus
- Průmysl nápojů. Kvasný průmysl. Průmysl pochutin
- NML Fields
- biochemie
- zemědělství a potravinářství
A complex of osmium tetroxide with 2,2'-bipyridine (Os,bipy) has been applied as a chemical probe of DNA structure as well as an electroactive DNA label. The Os,bipy has been known to form covalent adducts with pyrimidine DNA bases. Besides the pyrimidines, electrochemically active covalent adducts with Os,bipy are formed also by tryptophan (W) residues in peptides and proteins. In this paper we show that Os,bipy-treated proteins possessing W residues (such as avidin, streptavidin, or lysozyme) yield at the pyrolytic graphite electrode (PGE) a specific signal (peak alphaW) the potential of which differs from the potentials of signals produced by free Os,bipy or by Os,bipy-modified DNA. No such signal is observed with proteins lacking W (such as ribonuclease A or alpha-synuclein). Subpicomole amounts of W-containing proteins modified with Os,bipy can easily be detected using adsorptive transfer stripping voltammetry with the PGE. Binding of biotin to avidin interferes with Os,bipy modification of the protein, in agreement with the location of W residues within the biotin-binding site of avidin. These Ws are accessible for modification in the absence of biotin but hidden (protected from modification) in the avidin-biotin complex. The Os,bipy-modified avidin is unable to bind biotin, and its quarternary structure is disrupted. Analogous effects were observed with another biotin-binding protein, streptavidin. Our results demonstrate that modification of proteins with Os,bipy under conditions close to physiological, followed by a simple electrochemical analysis, can be applied in the microanalysis of protein structure and interactions.
- MeSH
- 2,2'-Dipyridyl chemistry MeSH
- Avidin chemistry MeSH
- Biotin chemistry MeSH
- Electrochemistry MeSH
- Electrodes MeSH
- Electrons MeSH
- Financing, Organized MeSH
- Molecular Structure MeSH
- Osmium Tetroxide analysis chemistry MeSH
- Proteins analysis chemistry MeSH
- Cross-Linking Reagents chemistry MeSH
- Tryptophan analysis chemistry MeSH
- Carbon chemistry MeSH
... 4.3.5 Fluorescent Markers Make Possible the -- Visualization of Proteins in the Cell 103 -- 4.4 Peptides ... ... 238 -- 9.2 Making a Fast Reaction Faster: Carbonic -- Anhydrases 239 -- 9.24 Carbonic Anhydrase Contains ... ... a Lipid Based on a Steroid -- Nucleus 325 -- 12.3.5 A Membrane Lipid Is an Amphipathic Molecule Containing ... ... 382 -- 14.2.3 Stages in the Extraction of Energy from -- Foodstuffs 382 -- 14.3 Metabolic Pathways Contain ... ... Phosphoglucomutase Converts Glucose -- 1-phosphate into Glucose 6-phosphate 581 -- 21.1.4 Liver Contains ...
5th ed. xvii, 974 s. : il., tab., grafy ; 32 cm
... in Breast Cancer -- 586 -- 15.4 Uses of Radioactive Iodide 589 -- 16 BIOCHEMISTRY OF HORMONES II: PEPTIDE ... ... Coli 768 20.4 The Tryptophan Operon of E. ... ... Awad, Jr. 22.1 Iron Metabolism: Overview 855 22.2 Iron-Containing Proteins 856 22.3 Intestinal Absorption ...
2nd edit 1016 s. : obr., tab., přeruš.bibliogr.
... the Effect of Amino Acids on the Central Action of L-Cycloserine with Regard to the Metabolism of Tryptophan ... ... Cybulska -- Studies on the Peptide Antibiotic Tetaine 476 -- A. Zugaza and A. ... ... Lengyel -- Studies on the Elimination of CO2 Gas Containing Foam Formed in Penicillium chryso genum Deep ...
778 s. : il.
... Applicability (170—176) 33 -- Chemically Modified Paper (178—191) 33 — 34 -- Sheets of Materials Containing ... ... -- Detection and Determination (4773 — 4775) -- Solvent Systems for Peptides (4776 — 4791) -- Peptide ... ... Derivatives (4792 — 4807) -- Applications -- Chromatography of Synthetic Peptides and Investigation ... ... of Nonbiological Reactions (4808 — 4876) -- Peptides in Microorganisms (4877 — 4890) -- Plant Peptides ... ... Peptides and -- Their Metabolism (4939 — 4957) -- ^Studies on the Chemical Structure of Peptides and ...
706 s.
- Keywords
- Chromatografie,
- MeSH
- Chromatography, Paper MeSH
- Conspectus
- Biochemie. Molekulární biologie. Biofyzika
- NML Fields
- biochemie
