Isosulfan blue
Catalog Number: BT-272526
CAS Number: 68238-36-8
Molecular Formula: C27H31N2NaO6S2
Molecular Weight: 566.7 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Isosulfan blue is a synthetic dye that has been used for various purposes, including medical, environmental, and industrial applications. It is a water-soluble compound that belongs to the family of sulfonated phthalocyanine dyes. Isosulfan blue is also known as Lymphazurin, Patent Blue V, or Sulpho Cyanine 10.
Properties
CAS Number
68238-36-8
Product Name
Isosulfan blue
IUPAC Name
sodium;2-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]benzene-1,4-disulfonate
Molecular Formula
C27H31N2NaO6S2
Molecular Weight
566.7 g/mol
InChI
InChI=1S/C27H32N2O6S2.Na/c1-5-28(6-2)22-13-9-20(10-14-22)27(21-11-15-23(16-12-21)29(7-3)8-4)25-19-24(36(30,31)32)17-18-26(25)37(33,34)35;/h9-19H,5-8H2,1-4H3,(H-,30,31,32,33,34,35);/q;+1/p-1
InChI Key
NLUFDZBOHMOBOE-UHFFFAOYSA-M
SMILES
CCN(CC)C1=CC=C(C=C1)C(=C2C=CC(=[N+](CC)CC)C=C2)C3=C(C=CC(=C3)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+]
Solubility
In water, 9.45X10+4 mg/L at 25 °C (est)
Synonyms
P-4125;P-1888;Lymphazurin;Isosulfan Blue;Disulphin blau;2,5-Disulfophenyl isomer;PATENT BLUE VIOLET F & D VERSION;PATENT BLUE V (V F) (C.I. no 42045 );2-{[4-(Diethylamino)phenyl][4-(diethyliminio)-2,5-cyclohexadien-1-ylidene]methyl}-1,4-benzenedisulfonate;sodium,2-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]benzene-1,4-disulfonate
Canonical SMILES
CCN(CC)C1=CC=C(C=C1)C(=C2C=CC(=[N+](CC)CC)C=C2)C3=C(C=CC(=C3)S(=O)(=O)[O-])S(=O)(=O)[O-].[Na+]
Method of Synthesis or Extraction
Isosulfan blue can be synthesized by several methods, including the reaction of phthalic anhydride with urea and sulfuric acid, the reaction of phthalic acid with urea and sulfuric acid, and the reaction of phthalic acid with urea and sodium bisulfite. The efficiency and yield of each method vary depending on the reaction conditions, such as temperature, pressure, and reaction time. The most commonly used method is the reaction of phthalic anhydride with urea and sulfuric acid, which yields isosulfan blue with a purity of over 95%. However, this method requires high temperature and pressure, which can be hazardous and energy-intensive. Environmental and safety considerations should be taken into account when synthesizing isosulfan blue, as the reaction byproducts can be toxic and harmful to the environment.
Chemical Structure and Biological Activity
The chemical structure of isosulfan blue consists of a phthalocyanine core with four sulfonate groups attached to the peripheral positions. Isosulfan blue has a molecular weight of 961.06 g/mol and a molecular formula of C37H27N3Na2O9S3. Isosulfan blue has been shown to have biological activity, particularly in the field of medical research. It is used as a diagnostic tool for lymphatic mapping and sentinel lymph node biopsy in breast cancer and melanoma patients. Isosulfan blue binds to albumin and is transported through the lymphatic system, allowing for the identification of the sentinel lymph node. Isosulfan blue has also been investigated for its potential use in photodynamic therapy, which involves the activation of a photosensitizer by light to induce cell death.
Biological Effects
Isosulfan blue has been shown to have effects on cell function and signal transduction. It has been reported to inhibit the activity of protein kinase C, which is involved in cell proliferation and differentiation. Isosulfan blue has also been shown to induce apoptosis, or programmed cell death, in cancer cells. However, isosulfan blue can have potential therapeutic and toxic effects, depending on the dose and route of administration. In clinical trials, isosulfan blue has been shown to be safe and effective for lymphatic mapping and sentinel lymph node biopsy. However, rare cases of anaphylaxis and allergic reactions have been reported.
Applications
Isosulfan blue has various applications in medical, environmental, and industrial research. In medical research, isosulfan blue is used for lymphatic mapping and sentinel lymph node biopsy in breast cancer and melanoma patients. It is also being investigated for its potential use in photodynamic therapy for cancer treatment. In environmental research, isosulfan blue is used as a tracer dye to study water flow and pollution in rivers and lakes. It can also be used to monitor the effectiveness of wastewater treatment plants. In industrial research, isosulfan blue is used in the manufacturing of textiles, paper, and plastics. It can also be used to improve product quality and efficiency in various industries. Health and safety considerations should be taken into account when using isosulfan blue, as it can be toxic and harmful to the environment.
Future Perspectives and Challenges
The use and study of isosulfan blue face several limitations and challenges. One of the main challenges is the potential for toxicity and adverse effects, particularly in high doses or prolonged exposure. Another challenge is the limited availability and high cost of isosulfan blue, which can limit its use in research and clinical settings. Future research should focus on developing safer and more efficient methods of synthesis or extraction, as well as investigating the potential therapeutic and toxic effects of isosulfan blue. Possible solutions and improvements include the development of new formulations and delivery methods, as well as the use of alternative dyes with similar properties. Future trends and prospects in the application of isosulfan blue in scientific research include the development of new diagnostic and therapeutic tools for cancer treatment, as well as the use of isosulfan blue as a tracer dye for environmental monitoring and pollution management.
Conclusion:
Isosulfan blue is a synthetic dye that has various applications in medical, environmental, and industrial research. It has a complex chemical structure and biological activity, which make it a valuable tool for lymphatic mapping, sentinel lymph node biopsy, and photodynamic therapy. However, isosulfan blue can have potential therapeutic and toxic effects, depending on the dose and route of administration. Health and safety considerations should be taken into account when using isosulfan blue, as it can be toxic and harmful to the environment. Future research should focus on developing safer and more efficient methods of synthesis or extraction, as well as investigating the potential therapeutic and toxic effects of isosulfan blue.
Conclusion:
Isosulfan blue is a synthetic dye that has various applications in medical, environmental, and industrial research. It has a complex chemical structure and biological activity, which make it a valuable tool for lymphatic mapping, sentinel lymph node biopsy, and photodynamic therapy. However, isosulfan blue can have potential therapeutic and toxic effects, depending on the dose and route of administration. Health and safety considerations should be taken into account when using isosulfan blue, as it can be toxic and harmful to the environment. Future research should focus on developing safer and more efficient methods of synthesis or extraction, as well as investigating the potential therapeutic and toxic effects of isosulfan blue.
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