Aeruginosin 865 - CAS 1611990-01-2

Aeruginosin 865 - CAS 1611990-01-2 Catalog number: BADC-00816

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Aeruginosin 865 is isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93 with anti-inflammatory effect. It is the first aeruginosin-type peptide containing both a fatty acid and a carbohydrate moiety. Aeruginosin 865 inhibits translocation of NF-kB to the nucleus.

Category
ADCs Cytotoxin
Product Name
Aeruginosin 865
CAS
1611990-01-2
Catalog Number
BADC-00816
Molecular Formula
C41H64N6O14
Molecular Weight
864.98
Target
Aeruginosin 865

Ordering Information

Catalog Number Size Price Quantity
BADC-00816 -- $--
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Description
Aeruginosin 865 is isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93 with anti-inflammatory effect. It is the first aeruginosin-type peptide containing both a fatty acid and a carbohydrate moiety. Aeruginosin 865 inhibits translocation of NF-kB to the nucleus.
IUPAC Name
(2S,3S,4S,5S,6R)-6-[[(2R,3aR,5S,6S,7aS)-2-[4-(diaminomethylideneamino)butylcarbamoyl]-5-hexanoyloxy-1-[(2R)-2-[[(2R)-2-hydroxy-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]-2,3,3a,4,5,6,7,7a-octahydroindol-6-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Canonical SMILES
CCCCCC(=O)OC1CC2CC(N(C2CC1OC3C(C(C(C(O3)C(=O)O)O)O)O)C(=O)C(CC(C)C)NC(=O)C(CC4=CC=C(C=C4)O)O)C(=O)NCCCCN=C(N)N
InChI
InChI=1S/C41H64N6O14/c1-4-5-6-9-31(50)59-29-19-23-18-27(36(54)44-14-7-8-15-45-41(42)43)47(26(23)20-30(29)60-40-34(53)32(51)33(52)35(61-40)39(57)58)38(56)25(16-21(2)3)46-37(55)28(49)17-22-10-12-24(48)13-11-22/h10-13,21,23,25-30,32-35,40,48-49,51-53H,4-9,14-20H2,1-3H3,(H,44,54)(H,46,55)(H,57,58)(H4,42,43,45)/t23-,25-,26+,27-,28-,29+,30+,32+,33+,34+,35+,40-/m1/s1
InChIKey
GYBRMQYCKSSXID-RIDHWVDWSA-N
Solubility
10 mm in DMSO
In Vitro
Aeruginosin 865 (pretreatment with 0.1-100 μg/mL) shows significant inhibition of IL-8 (EC50=3.5 μg/mL) and ICAM-1 (EC50=50.0 μg/mL) in hTNF-α-stimulated HLMVECs in a concentration-dependent manner. Aeruginosin 865 does not affect cell viability, even at much higher concentration in HeLa, HepG2 cells. Aeruginosin 865 (100-200 μM) shows high-dose cytotoxicity in Mouse fibrosarcoma cells and with no cytotoxic effect in NIH/3T3 cells.
Purity
>98.0%
Shelf Life
≥ 2 years
Shipping
Room temperature
Storage
-20°C
1. 15 N Stable Isotope Labeling and Comparative Metabolomics Facilitates Genome Mining in Cultured Cyanobacteria
Tyler A Wilson,Camila M Crnkovic,Jimmy E Orjala,Daniel S May,James R Fuchs,Aleksej Krunic ACS Chem Biol . 2020 Mar 20;15(3):758-765. doi: 10.1021/acschembio.9b00993.
As genome mining becomes a more widely used approach to identify bacterial natural products, the challenge of matching biosynthetic gene clusters to their cognate secondary metabolites has become more apparent. Bioinformatic platforms such as AntiSMASH have made great progress in predicting chemical structures from genetic information, however the predicted structures are often incomplete. This complicates identifying the predicted compounds by mass spectrometry. Secondary metabolites produced by cyanobacteria represent a unique opportunity for bridging this gap. Cultured cyanobacteria incorporate inorganic nitrogen provided in chemically defined media into all nitrogen-containing secondary metabolites. Thus, stable isotope labeling with15N labeled nitrate and subsequent comparative metabolomics can be used to match biosynthetic gene clusters to their cognate compounds in cell extracts. Analysis of the sequenced genome ofNostocsp. UIC 10630 identified six biosynthetic gene clusters predicted to encode the production of a secondary metabolite with at least one nitrogen atom. Comparative metabolomic analysis of the15N labeled and unlabeled cell extracts revealed four nitrogen containing compounds that contained the same number of nitrogen atoms as were predicted in the biosynthetic gene clusters. Two of the four compounds were new secondary metabolites, and their structures were elucidated by NMR, HRESIMS, and MS/MS.
2. Separation of Aeruginosin-865 from Cultivated Soil Cyanobacterium (Nostoc sp.) by Centrifugal Partition Chromatography combined with Gel Permeation Chromatography
Rabya Aslam,Petra Urajová,José Cheel,Pavel Hrouzek,Jiří Kopecký,Mirjana Minceva Nat Prod Commun . 2015 Oct;10(10):1719-22.
Aeruginosin-865 was isolated from cultivated soil cyanobacteria using a combination of centrifugal partition chromatography (CPC) and gel permeation chromatography. The solubility of Aer-865 in different solvents was evaluated using the conductor-like screening model for real solvents (COSMO-RS). The CPC separation was performed in descending mode with a biphasic solvent system composed of water-n-BuOH-acetic acid (5:4:1, v/v/v). The upper phase was used as a stationary phase, whereas the lower phase was employed as a mobile phase at a flow rate of 10 mL/min. The revolution speed and temperature of the separation column were 1700 rpm and 25 degrees C, respectively. Preparative CPC separation followed by gel permeation chromatography was performed on 50 mg of crude extract yielding Aer-865 (3.5 mg), with a purity over 95% as determined by HPLC. The chemical identity of the isolated compound was confirmed by comparing its spectroscopic data (UV, HRESI-MS, HRESI-MS/MS) with those of an authentic standard and data available in the literature.
3. Novel Aeruginosin-865 from Nostoc sp. as a potent anti-inflammatory agent
Jouni Jokela,Maren Pflüger,Harald Hundsberger,Aleksandra Kapuścik,Pavel Hrouzek,Petr Novák,Andreas Eger,Marek Kuzma,Jiří Kopecký,Simona Bártová Chembiochem . 2013 Nov 25;14(17):2329-37. doi: 10.1002/cbic.201300246.
Aeruginosin-865 (Aer-865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin-type peptide containing both a fatty acid and a carbohydrate moiety, and is the first aeruginosin to be found in the genus Nostoc. Mass spectrometry, chemical and spectroscopic analysis as well as one- and two-dimensional NMR and chiral HPLC analysis of Marfey derivatives were applied to determine the peptidic sequence: D-Hpla, D-Leu, 5-OH-Choi, Agma, with hexanoic and mannopyranosyl uronic acid moieties linked to Choi. We used an AlphaLISA assay to measure the levels of proinflammatory mediators IL-8 and ICAM-1 in hTNF-α-stimulated HLMVECs. Aer-865 showed significant reduction of both: with EC50 values of (3.5±1.5) μg mL(-1) ((4.0±1.7) μM) and (50.0±13.4) μg mL(-1) ((57.8±15.5) μM), respectively. Confocal laser scanning microscopy revealed that the anti-inflammatory effect of Aer-865 was directly associated with inhibition of NF-κB translocation to the nucleus. Moreover, Aer-865 did not show any cytotoxic effect.

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