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:
Quality Level
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
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Zeqi Qi et al.
Phytopathology, 115(2), 139-150 (2024-10-22)
Due to a lack of understanding of the disease epidemiology and comprehensive control measures, tea leaf spot caused by Didymella segeticola has a significant negative impact on tea yield and quality in the tea plantations of Southwest China. Phenazine-1-carboxamide (PCN)
Phenazine production promotes antibiotic tolerance and metabolic heterogeneity in Pseudomonas aeruginosa biofilms
Schiessl KT, et al.
Nature Communications, 10 (2019)
Lluïsa Vilaplana et al.
Analytical and bioanalytical chemistry, 412(24), 5897-5912 (2020-05-29)
Infectious diseases are still a worldwide important problem. This fact has led to the characterization of new biomarkers that would allow an early, fast and reliable diagnostic and targeted therapy. In this context, Pseudomonas aeruginosa can be considered one of
The role of phenazines in marine Pseudomonas aeruginosa microbiologically influenced corrosion against 316L stainless steel
Yi Yang, et al.
Corrosion Science, 242, 112587-112587 (2025)
Mechanistic study of a low-power bacterial maintenance state using high-throughput electrochemistry.
John A Ciemniecki et al.
Cell, 187(24), 6882-6895 (2024-10-25)
Mechanistic studies of life's lower metabolic limits have been limited due to a paucity of tractable experimental systems. Here, we show that redox-cycling of phenazine-1-carboxamide (PCN) by Pseudomonas aeruginosa supports cellular maintenance in the absence of growth with a low
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