Isosulfan blue
Solid powder
Materials Science
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.
566.7 g/mol
566.7 g/mol
Formulation:
566.7 g/mol
Source:
Usage:
Isosulfan blue
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-272526
CAS Number: 68238-36-8
Molecular Formula: C27H31N2NaO6S2
Molecular Weight: 566.7 g/mol
Purity: ≥ 98%
Inventory: In Stock
| Size | SKU | Price | |
|---|---|---|---|
| 5mg | bt-272526-5mg | $956.92 | |
| 10mg | bt-272526-10mg | $1,239.54 | |
| 50mg | bt-272526-50mg | $3,845.69 |
| CAS Number | 68238-36-8 |
|---|---|
| Product Name | Isosulfan blue |
| Molecular Formula | C27H31N2NaO6S2 |
| Molecular Weight | 566.7 g/mol |
| Appearance | Solid powder |
| Colorform | Blue-green liquid |
| 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 |
| IUPAC Name | 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+] |
| 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. |
| 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. |
| Other CAS Number | 68238-36-8 |
| Pictograms | Irritant |
| Shelf Life | >3 years if stored properly |
| 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) |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| 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 |
| Vapor Pressure | 1.87X10-36 mm Hg at 25 °C (est) |
| Reference | 1. Krag DN, Anderson SJ, Julian TB, Brown AM, Harlow SP, Costantino JP, Ashikaga T, Weaver DL, Mamounas EP, Jalovec LM, Frazier TG, Noyes RD, Robidoux A, Scarth HM, Wolmark N. Sentinel-lymph-node resection compared with conventional axillary-lymph-node dissection in clinically node-negative patients with breast cancer: overall survival findings from the NSABP B-32 randomised phase 3 trial. Lancet Oncol. 2010 Oct;11(10):927-33. doi: 10.1016/S1470-2045(10)70207-2. PMID: 20863759; PMCID: PMC3041644. 2. Frumovitz M, Plante M, Lee PS, Sandadi S, Lilja JF, Escobar PF, Gien LT, Urbauer DL, Abu-Rustum NR. Near-infrared fluorescence for detection of sentinel lymph nodes in women with cervical and uterine cancers (FILM): a randomised, phase 3, multicentre, non-inferiority trial. Lancet Oncol. 2018 Oct;19(10):1394-1403. doi: 10.1016/S1470-2045(18)30448-0. Epub 2018 Aug 22. PMID: 30143441; PMCID: PMC6580418. 3. Backes FJ, Cohen D, Salani R, Cohn DE, O'Malley DM, Fanning E, Suarez AA, Fowler JM. Prospective clinical trial of robotic sentinel lymph node assessment with isosulfane blue (ISB) and indocyanine green (ICG) in endometrial cancer and the impact of ultrastaging (NCT01818739). Gynecol Oncol. 2019 Jun;153(3):496-499. doi: 10.1016/j.ygyno.2019.03.252. Epub 2019 Apr 4. PMID: 31230614. 4. Bézu C, Coutant C, Salengro A, Daraï E, Rouzier R, Uzan S. Anaphylactic response to blue dye during sentinel lymph node biopsy. Surg Oncol. 2011 Mar;20(1):e55-9. doi: 10.1016/j.suronc.2010.10.002. Epub 2010 Nov 11. PMID: 21074413. 5. Alvarado MD, Mittendorf EA, Teshome M, Thompson AM, Bold RJ, Gittleman MA, Beitsch PD, Blair SL, Kivilaid K, Harmer QJ, Hunt KK. SentimagIC: A Non-inferiority Trial Comparing Superparamagnetic Iron Oxide Versus Technetium-99m and Blue Dye in the Detection of Axillary Sentinel Nodes in Patients with Early-Stage Breast Cancer. Ann Surg Oncol. 2019 Oct;26(11):3510-3516. doi: 10.1245/s10434-019-07577-4. Epub 2019 Jul 11. Erratum in: Ann Surg Oncol. 2020 Jun 8;: PMID: 31297674. |
| PubChem Compound | Isosulfan blue |
| Last Modified | May 30 2023 |