Aeruginosin 865

Aeruginosin 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. Aeruginosin 865 inhibits translocation of NF-kB to the nucleus. Aeruginosin 865 has anti-inflammatory effect.

Product information

CAS Number: 1611990-01-2

Molecular Weight: 864.98

Formula: C41H64N6O14

Chemical Name: (2S, 3S, 4S, 5S, 6R)-6-{[(2R, 3aR, 5S, 6S, 7aS)-2-[(4-carbamimidamidobutyl)carbamoyl]-5-(hexanoyloxy)-1-[(2R)-2-[(2R)-2-hydroxy-3-(4-hydroxyphenyl)propanamido]-4-methylpentanoyl]-octahydro-1H-indol-6-yl]oxy}-3, 4, 5-trihydroxyoxane-2-carboxylic acid

Smiles: CC(C)C[C@@H](NC(=O)[C@H](O)CC1C=CC(O)=CC=1)C(=O)N1[C@H](C[C@@H]2C[C@H](OC(=O)CCCCC)[C@H](C[C@H]12)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@@H]1O)C(O)=O)C(=O)NCCCCNC(N)=N

InChiKey: GYBRMQYCKSSXID-RIDHWVDWSA-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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

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.

References:

1. Aleksandra Kapuścik, et al. Novel Aeruginosin-865 from Nostoc sp. as a potent anti-inflammatory agent. Chembiochem. 2013 Nov 25;14(17):2329-37.
2. Ivana Veselá, et al. Cytotoxic Effect of Aeruginosin-865, Resveratrol and Capsaicin on Mouse Fibroblasts and Cells Derived from Fallow Deer. Natural Product Communications, Volume: 13 issue: 2.

Products are for research use only. Not for human use.