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MilliporeSigma

SML4202

Phenazine-1-carboxamide

≥98% (HPLC), powder, antimicrobial

Synonym(s):

1-​Phenazinecarboxamide, Oxychloraphin, Oxychlororaphine

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About This Item

Empirical Formula (Hill Notation):
C13H9N3O
CAS Number:
Molecular Weight:
223.23
MDL number:
NACRES:
NA.21
Assay:
≥98% (HPLC)
Form:
powder
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Quality Segment

assay

≥98% (HPLC)

form

powder

color

light green to dark beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

O=C(N)C1=CC=CC2=NC3=CC=CC=C3N=C21

General description

Phenazine-1-carboxamide is a secondary metabolite produced by Pseudomonas aeruginosa that promotes biofilm formation in soil, as well as chronic infections in human lungs. It facilitates an anaerobic survival metabolism in biofilm regions where oxygen is unavailable, rendering cells physiologically tolerant to conventional drugs. Phenazine-1-carboxamide inducesDAF-7/TGF-b expression in C. elegans necessary for the behavioral avoidance response to P. aeruginosa. Phenazine-1-carboxamide and other phenazines enable Pseudomonas species to eliminate competitors for rhizosphere colonization. Phenazine-1-carboxamide exhibits antibacterial and anti-fungal effects against Xanthomonas citri, and Staphylococcus aureus, including the methicillin-resistant strain (MRSA). Phenazine-1-carboxamide is involved in the regulation of various cellular processes, including iron acquisition and signaling, which are essential for the establishment and maintenance of biofilms. The compound has been shown to enhance the bacterium′s virulence by facilitating its ability to adhere to surfaces and resist antimicrobial treatments.

Application

Phenazine-1-carboxamide may be used:
  • to study its antifungal properties against various plant pathogens
  • its role in enhancing the corrosion rate of 316L stainless steel when exposed to Pseudomonas aeruginosa, demonstrating its impact on microbiologically influenced corrosion through the regulation of phenazine secretion


Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable



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