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Merck
CN

SML4202

Phenazine-1-carboxamide

new

≥98% (HPLC), powder, antimicrobial

别名:

1-​Phenazinecarboxamide, Oxychloraphin, Oxychlororaphine

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关于此项目

经验公式(希尔记法):
C13H9N3O
化学文摘社编号:
分子量:
223.23
MDL编号:
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质量水平

方案

≥98% (HPLC)

表单

powder

颜色

light green to dark beige

溶解性

DMSO: 2 mg/mL, clear (warmed)

储存温度

2-8°C

SMILES字符串

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

一般描述

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.

应用

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

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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)
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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