1,2-Naphthoquinone-4-sulfonic acid sodium salt - 521-24-4

1,2-Naphthoquinone-4-sulfonic acid sodium salt

Catalog Number: EVT-299489
CAS Number: 521-24-4
Molecular Formula: C10H5NaO5S
Molecular Weight: 260.2 g/mol
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Product Introduction

Description

1,2-Naphthoquinone-4-sulfonic acid sodium salt (NQS) is a chemical reagent that has been explored for its utility in various analytical and biological applications. Its unique chemical properties allow it to interact with different substances, making it a valuable tool in both spectrophotometric analysis and the study of antibacterial mechanisms. The following analysis delves into the research surrounding NQS, examining its mechanism of action and its applications in different fields, as evidenced by the studies provided.

Applications in Various Fields

The research on 2-methyl-1,4-naphthoquinone's antibacterial action provides insights into the potential microbiological applications of NQS. By understanding the mechanism through which naphthoquinone derivatives exert their antibacterial effects, NQS could be investigated for its use as an antibacterial agent or as a tool in studying bacterial resistance mechanisms. The interaction with sulfhydryl groups suggests that NQS and its derivatives could be used to probe the function of bacterial enzymes and metabolites that contain these groups2.

Properties

CAS Number

521-24-4

Product Name

1,2-Naphthoquinone-4-sulfonic acid sodium salt

IUPAC Name

sodium;3,4-dioxonaphthalene-1-sulfonate

Molecular Formula

C10H5NaO5S

Molecular Weight

260.2 g/mol

InChI

InChI=1S/C10H6O5S.Na/c11-8-5-9(16(13,14)15)6-3-1-2-4-7(6)10(8)12;/h1-5H,(H,13,14,15);/q;+1/p-1

InChI Key

UBLXEEBHYISRFM-UHFFFAOYSA-M

SMILES

C1=CC=C2C(=C1)C(=CC(=O)C2=O)S(=O)(=O)[O-].[Na+]

Synonyms

3,4-Dihydro-3,4-dioxo-1-naphthalenesulfonic Acid Sodium Salt; 3,4-Dihydro-3,4-dioxo- 1-naphthalenesulfonic Acid Sodium Salt; 1,2-Naphthoquinone-4-sodium Sulfonate; 1,2-Naphthoquinone-4-sulfonic Acid Sodium Salt; Sodium 1,2-Naphthoquinone-4-sulfonate;

Canonical SMILES

C1=CC=C2C(=C1)C(=CC(=O)C2=O)S(=O)(=O)[O-].[Na+]

Isomeric SMILES

C1=CC=C2C(=C1)C(=CC(=O)C2=O)S(=O)(=O)[O-].[Na+]
Mechanism of Action

The antibacterial properties of naphthoquinone derivatives have been a subject of interest in the scientific community. A study on the mechanism of antibacterial action of 2-methyl-1,4-naphthoquinone, a compound structurally related to NQS, revealed that its effectiveness against Escherichia coli could be neutralized by certain sulfur-containing reducing agents. This suggests that the antibacterial action may involve the interaction with sulfhydryl groups of essential bacterial enzymes or metabolites, potentially by blocking these groups. The study indicates that the position on the quinone ring is crucial for this interaction, as modifications to the structure can abolish or retain antibacterial activity2.

Applications in Analytical Chemistry

NQS has been utilized as a reagent for the detection of amphetamines in urine samples. A developed extractive-spectrophotometric method using NQS demonstrated the ability to detect amphetamine concentrations ranging from 1.4 to 50 mg L^-1 with a detection limit of 0.6 mg L^-1. The method's accuracy was confirmed by evaluating constant bias errors and using a placebo control. This application showcases NQS's potential in forensic and clinical toxicology for drug monitoring1.

In another application, NQS was employed as a derivatizing agent for primary and secondary aliphatic amines in aqueous solutions, followed by separation using reversed-phase high-performance liquid chromatography. The method proved generally reliable, although it faced limitations with certain amines due to steric hindrance and solubility issues during the derivatization and extraction processes. This highlights NQS's role in enhancing the detection of low levels of amines in environmental and biological samples3.

Method of Synthesis or Extraction
1,2-Naphthoquinone-4-sulfonic acid sodium salt can be synthesized by various methods, including the reaction of 1,2-naphthoquinone with sulfamic acid or sodium sulfite, or by the oxidation of 1,2-dihydro-1,2-naphthoquinone with sodium hypochlorite. The efficiency and yield of each method depend on the reaction conditions, such as temperature, pH, and reaction time. The reaction of 1,2-naphthoquinone with sulfamic acid has been reported to yield up to 90% of 1,2-Naphthoquinone-4-sulfonic acid sodium salt, while the oxidation of 1,2-dihydro-1,2-naphthoquinone with sodium hypochlorite has a lower yield of around 50%. Environmental and safety considerations should also be taken into account when synthesizing 1,2-Naphthoquinone-4-sulfonic acid sodium salt, as some of the reactants and by-products can be hazardous to human health and the environment.
Chemical Structure and Biological Activity
The chemical structure of 1,2-Naphthoquinone-4-sulfonic acid sodium salt consists of a naphthoquinone core with a sulfonic acid group and a sodium salt. 1,2-Naphthoquinone-4-sulfonic acid sodium salt has been shown to exhibit various biological activities, including antimicrobial, antitumor, and anti-inflammatory effects. The mechanism of action of 1,2-Naphthoquinone-4-sulfonic acid sodium salt involves the generation of reactive oxygen species (ROS) and the inhibition of enzymes involved in cellular respiration and DNA synthesis. 1,2-Naphthoquinone-4-sulfonic acid sodium salt has been found to target various biological molecules, such as proteins, lipids, and nucleic acids, and has shown potent bioactivity against cancer cells and pathogenic microorganisms.
Biological Effects
1,2-Naphthoquinone-4-sulfonic acid sodium salt has been shown to affect cell function and signal transduction pathways by modulating the activity of various enzymes and proteins. 1,2-Naphthoquinone-4-sulfonic acid sodium salt has been reported to induce apoptosis, cell cycle arrest, and DNA damage in cancer cells, while also inhibiting the growth of pathogenic bacteria and fungi. 1,2-Naphthoquinone-4-sulfonic acid sodium salt has also been investigated for its potential therapeutic and toxic effects in vivo, with promising results in animal models of cancer and infectious diseases. However, the toxicity of 1,2-Naphthoquinone-4-sulfonic acid sodium salt in humans is still unclear, and further studies are needed to determine its safety and efficacy.
Future Perspectives and Challenges
Despite the promising applications of 1,2-Naphthoquinone-4-sulfonic acid sodium salt, there are still several challenges that need to be addressed. The toxicity and safety of 1,2-Naphthoquinone-4-sulfonic acid sodium salt in humans need to be thoroughly evaluated, and the mechanisms of its biological activity need to be further elucidated. The synthesis of 1,2-Naphthoquinone-4-sulfonic acid sodium salt also needs to be optimized to improve its efficiency and yield, while minimizing its environmental impact. Future research should focus on developing new methods of synthesis and exploring the potential of 1,2-Naphthoquinone-4-sulfonic acid sodium salt in various fields of research, such as nanotechnology and biotechnology.
Conclusion:
In conclusion, 1,2-Naphthoquinone-4-sulfonic acid sodium salt is a versatile compound with diverse applications in medical, environmental, and industrial research. The synthesis, chemical structure, biological activity, and applications of 1,2-Naphthoquinone-4-sulfonic acid sodium salt have been extensively studied, with promising results in various fields of research. However, further studies are needed to fully understand the potential of 1,2-Naphthoquinone-4-sulfonic acid sodium salt and to address the challenges associated with its use.

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