Hemipyocyanine

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Hemipyocyanine
Category Antibiotics
Catalog number BBF-01814
CAS 528-71-2
Molecular Weight 196.21
Molecular Formula C12H8N2O
Purity >95%

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Description

Hemipyocyanine, an α-Amylase inhibitor, is produced by the strain of Pseudomonas aeruginosa. It has anti-gram-positive bacteria, negative-bacteria, trichophyta, yeast and other fungi activities.

Specification

Synonyms 1-Hydroxyphenazine; 1-Phenazinol; Pyoxanthose; NSC 88882; Phenazine, 1-hydroxy-; 1-Hydroxy-5,10-diazaanthracene; 5H-phenazin-1-one; alpha-Hydroxyphenazine; 1-Hydroxy-9,10-diazaanthracene; Hemipyocyanin; Pyoxanthose; α-Hydroxyphenazine
Storage Store at -20°C
IUPAC Name phenazin-1-ol
Canonical SMILES C1=CC=C2C(=C1)N=C3C=CC=C(C3=N2)O
InChI InChI=1S/C12H8N2O/c15-11-7-3-6-10-12(11)14-9-5-2-1-4-8(9)13-10/h1-7,15H
InChI Key SVRNCBGWUMMBQB-UHFFFAOYSA-N
Source Pseudomonas aeruginosa

Properties

Appearance Yellow Ribbed Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Fungi; Yeast
Boiling Point 430.0±10.0°C at 760 mmHg
Melting Point 158°C
Density 1.376±0.06 g/cm3
Solubility Soluble in DMF, DMSO, Ethanol, Methanol, Water (Poorly)

Reference Reading

1. Novel α-Amylase Inhibitor Hemi-Pyocyanin Produced by Microbial Conversion of Chitinous Discards
Van Bon Nguyen, San-Lang Wang, Thi Hanh Nguyen, Thi Ngoc Tran, Chien Thang Doan, Anh Dzung Nguyen, Manh Dung Doan Mar Drugs . 2022 Apr 23;20(5):283. doi: 10.3390/md20050283.
α-Amylase inhibitors (aAIs) have been applied for the efficient management of type 2 diabetes. The aim of this study was to search for potential aAIs produced by microbial fermentation. Among various bacterial strains,Pseudomonas aeruginosaTUN03 was found to be a potential aAI-producing strain, and shrimp heads powder (SHP) was screened as the most suitable C/N source for fermentation.P. aeruginosaTUN03 exhibited the highest aAIs productivity (3100 U/mL) in the medium containing 1.5% SHP with an initial pH of 7-7.5, and fermentation was performed at 27.5 °C for two days. Further, aAI compounds were investigated for scaled-up production in a 14 L-bioreactor system. The results revealed a high yield (4200 U/mL) in a much shorter fermentation time (12 h) compared to fermentation in flasks. Bioactivity-guided purification resulted in the isolation of one major target compound, identified as hemi-pyocyanin (HPC) via gas chromatography-mass spectrometry and nuclear magnetic resonance. Its purity was analyzed by high-performance liquid chromatography. HPC demonstrated potent α-amylase inhibitory activity comparable to that of acarbose, a commercial antidiabetic drug. Notably, HPC was determined as a new aAI. The docking study indicated that HPC inhibits α-amylase by binding to amino acid Arg421 at the biding site on enzyme α-amylase with good binding energy (-9.3 kcal/mol) and creating two linkages of H-acceptors.

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