Barbamide
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| Category | Bioactive by-products |
| Catalog number | BBF-00266 |
| CAS | |
| Molecular Weight | 461.83 |
| Molecular Formula | C20H23Cl3N2O2S |
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Description
Barbamide is produced by the strain of Lyn-gbya majiuscula. It has the activity of killing mollusks.
Specification
| Synonyms | CHEBI:80028 |
| IUPAC Name | (E,5S)-6,6,6-trichloro-3-methoxy-N,5-dimethyl-N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]hex-2-enamide |
| Canonical SMILES | CC(CC(=CC(=O)N(C)C(CC1=CC=CC=C1)C2=NC=CS2)OC)C(Cl)(Cl)Cl |
| InChI | InChI=1S/C20H23Cl3N2O2S/c1-14(20(21,22)23)11-16(27-3)13-18(26)25(2)17(19-24-9-10-28-19)12-15-7-5-4-6-8-15/h4-10,13-14,17H,11-12H2,1-3H3/b16-13+/t14-,17-/m0/s1 |
| InChI Key | UGNRFJOMRFTXSQ-ITRHSTPOSA-N |
Properties
| Appearance | Yellow Oil |
| Antibiotic Activity Spectrum | parasites |
Reference Reading
1. Barbamide Displays Affinity for Membrane-Bound Receptors and Impacts Store-Operated Calcium Entry in Mouse Sensory Neurons
Andrea Hough, Connor Criswell, Asef Faruk, Jane E Cavanaugh, Benedict J Kolber, Kevin J Tidgewell Mar Drugs. 2023 Feb 2;21(2):110. doi: 10.3390/md21020110.
Marine cyanobacteria are a rich source of bio-active metabolites that have been utilized as leads for drug discovery and pharmacological tools for basic science research. Here, we describe the re-isolation of a well-known metabolite, barbamide, from Curaçao on three different occasions and the characterization of barbamide's biological interactions with targets of the mammalian nervous system. Barbamide was originally discovered as a molluscicidal agent from a filamentous marine cyanobacterium. In our hands, we found little evidence of toxicity against mammalian cell cultures. However, barbamide showed several affinities when screened for binding affinity for a panel of 45 receptors and transporters known to be involved in nociception and sensory neuron activity. We found high levels of binding affinity for the dopamine transporter, the kappa opioid receptor, and the sigma receptors (sigma-1 and sigma-2 also known as transmembrane protein 97; TMEM97). We tested barbamide in vitro in isolated sensory neurons from female mice to explore its functional impact on calcium flux in these cells. Barbamide by itself had no observable impact on calcium flux. However, barbamide enhanced the effect of the TRPV1 agonist capsaicin and enhanced store-operated calcium entry (SOCE) responses after depletion of intracellular calcium. Overall, these results demonstrate the biological potential of barbamide at sensory neurons with implications for future drug development projects surrounding this molecule.
2. Enzymatic α-Ketothioester Decarbonylation Occurs in the Assembly Line of Barbamide for Skeleton Editing
Shengjie Guo, Yueqian Sang, Chao Zheng, Xiao-Song Xue, Zhijun Tang, Wen Liu J Am Chem Soc. 2023 Feb 23. doi: 10.1021/jacs.2c10277. Online ahead of print.
The decarbonylation reaction has been developed significantly in organic chemistry as an effective approach to various synthetic applications, but enzymatic precedents for this reaction are rare. Based on investigations into the hybrid nonribosomal peptide synthetase (NRPS)-polyketide synthase (PKS) assembly line of barbamide, we report an on-line α-ketothioester decarbonylation reaction that leads to one-carbon truncation of the elongating skeleton. This enzymatic editing reaction occurs in the first round of lipopeptide extension and modification involving the multienzymes BarE and BarF, which successively house an NRPS module to initiate the biosynthesis and a PKS module to catalyze the first round of chain extension. Starting with processing a leucine-derived α-ketoacyl starter, the ketosynthase domain in BarE displays an unusual dual activity that results in net one-carbon chain elongation. It extrudes carbon monoxide from α-keto-isocaproyl thioester and then mediates decarboxylative condenses of the resultant isovaleryl thioester with malonyl thioester to form a diketide intermediate, followed by BarF-based O-methylation to stabilize the enol form of the β-carbonyl and afford an unusual E-double bond. Biochemical characterization, chemical synthesis, computational analysis, and the experimental outcome of site-directed mutagenesis illustrate the extraordinary catalytic capability of this ketosynthase domain. This work furthers the appreciation of assembly line chemistry and opens the door to new approaches for skeleton editing/engineering of related molecules using synthetic biology approaches.
3. The genetics, biosynthesis and regulation of toxic specialized metabolites of cyanobacteria
Leanne A Pearson, Elke Dittmann, Rabia Mazmouz, Sarah E Ongley, Paul M D'Agostino, Brett A Neilan Harmful Algae. 2016 Apr;54:98-111. doi: 10.1016/j.hal.2015.11.002.
The production of toxic metabolites by cyanobacterial blooms represents a significant threat to the health of humans and ecosystems worldwide. Here we summarize the current state of the knowledge regarding the genetics, biosynthesis and regulation of well-characterized cyanotoxins, including the microcystins, nodularin, cylindrospermopsin, saxitoxins and anatoxins, as well as the lesser-known marine toxins (e.g. lyngbyatoxin, aplysiatoxin, jamaicamides, barbamide, curacin, hectochlorin and apratoxins).
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
