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Merck
CN

SML4202

Phenazine-1-carboxamide

≥98% (HPLC), powder, antimicrobial

别名:

Oxychloraphin, Oxychlororaphine, 1-​Phenazinecarboxamide

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经验公式(希尔记法):
C13H9N3O
化学文摘社编号:
分子量:
223.23
MDL number:
NACRES:
NA.21
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
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SMILES string

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

assay

≥98% (HPLC)

form

powder

color

light green to dark beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

Quality Level

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)
Kaiquan Liu et al.
Frontiers in microbiology, 14, 1186052-1186052 (2023-05-12)
Phenazine-1-carboxylic acid (PCA) is a biologically active substance with the ability to prevent and control crop diseases. It was certified as a pesticide by the Ministry of Agriculture of China in 2011 and was named "Shenzimycin." Lzh-T5 is a Pseudomonas
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
Phenazine production promotes antibiotic tolerance and metabolic heterogeneity in Pseudomonas aeruginosa biofilms
Schiessl KT, et al.
Nature Communications, 10 (2019)
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)

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