Buy Indocyanine green (BT-271022)

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Indocyanine green

Catalog Number: BT-271022

CAS Number: 3599-32-4

Molecular Formula: C43H47N2NaO6S2

Molecular Weight: 774.9668

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Indocyanine green (ICG) is a water-soluble tricarbocyanine dye that has been used in various medical, environmental, and industrial applications. It is a near-infrared fluorescent dye that has a peak absorption at 800 nm and a peak emission at 830 nm. ICG has been approved by the US Food and Drug Administration (FDA) for use in humans since 1956. It is a safe and effective contrast agent that is widely used in medical imaging, ophthalmology, and liver function testing. This paper aims to provide a comprehensive review of ICG, including its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges.

Properties

CAS Number

3599-32-4

Product Name

Indocyanine green

IUPAC Name

sodium;4-[(2E)-2-[(2E,4E,6E)-7-[1,1-dimethyl-3-(4-sulfonatobutyl)benzo[e]indol-3-ium-2-yl]hepta-2,4,6-trienylidene]-1,1-dimethylbenzo[e]indol-3-yl]butane-1-sulfonate

Molecular Formula

C43H47N2NaO6S2

Molecular Weight

774.9668

InChI

InChI=1S/C43H48N2O6S2.Na/c1-42(2)38(44(28-14-16-30-52(46,47)48)36-26-24-32-18-10-12-20-34(32)40(36)42)22-8-6-5-7-9-23-39-43(3,4)41-35-21-13-11-19-33(35)25-27-37(41)45(39)29-15-17-31-53(49,50)51;/h5-13,18-27H,14-17,28-31H2,1-4H3,(H-,46,47,48,49,50,51);/q;+1/p-1

InChI Key

MOFVSTNWEDAEEK-UHFFFAOYSA-M

SMILES

CC1(C(=[N+](C2=C1C3=CC=CC=C3C=C2)CCCCS(=O)(=O)[O-])C=CC=CC=CC=C4C(C5=C(N4CCCCS(=O)(=O)[O-])C=CC6=CC=CC=C65)(C)C)C.[Na+]

Solubility

SOL IN WATER & METHANOL; PRACTICALLY INSOL IN MOST OTHER ORG SOLVENTS
Soluble in water, less soluble in ethanol.

Synonyms

Cardio Green
Cardio-Green
Cardiogreen
Green, Indocyanine
Indocyanine Green
Ujoveridin
Vofaverdin
Vophaverdin
Wofaverdin

Canonical SMILES

CC1(C(=[N+](C2=C1C3=CC=CC=C3C=C2)CCCCS(=O)(=O)[O-])C=CC=CC=CC=C4C(C5=C(N4CCCCS(=O)(=O)[O-])C=CC6=CC=CC=C65)(C)C)C.[Na+]

Isomeric SMILES

CC1(C(=[N+](C2=C1C3=CC=CC=C3C=C2)CCCCS(=O)(=O)[O-])/C=C/C=C/C=C/C=C/4\C(C5=C(N4CCCCS(=O)(=O)[O-])C=CC6=CC=CC=C65)(C)C)C.[Na+]

Method of Synthesis or Extraction

Indocyanine green can be synthesized by various methods, including chemical synthesis, microbial fermentation, and extraction from natural sources. The most commonly used method for the synthesis of Indocyanine green is the chemical method, which involves the reaction of indigo with chlorosulfonic acid and subsequent treatment with sodium hydroxide. The efficiency and yield of this method depend on the purity of the starting materials, the reaction conditions, and the purification process. The yield of Indocyanine green synthesis ranges from 30% to 70%, depending on the reaction conditions. The environmental and safety considerations of Indocyanine green synthesis include the use of hazardous chemicals, such as chlorosulfonic acid, which can cause severe burns and respiratory problems.

Chemical Structure and Biological Activity

Indocyanine green has a molecular weight of 775.0 g/mol and a chemical formula of C43H47N2O6S2Na. It has a planar structure with a central indocyanine chromophore and two sulfonate groups. Indocyanine green is highly water-soluble and has a low binding affinity to plasma proteins. The mechanism of action of Indocyanine green is based on its ability to bind to plasma proteins and to be taken up by cells. Indocyanine green has been shown to bind to albumin and lipoproteins, which are the major transport proteins in the blood. Indocyanine green has a high affinity for hepatocytes and is rapidly taken up by the liver. Indocyanine green has been used as a diagnostic tool for liver function testing, as it is rapidly cleared from the blood by the liver.

Biological Effects

Indocyanine green has been shown to have various biological effects on cell function and signal transduction. It has been shown to inhibit the activity of protein kinase C, which is involved in cell proliferation and differentiation. Indocyanine green has also been shown to activate the mitogen-activated protein kinase (MAPK) pathway, which is involved in cell survival and apoptosis. The potential therapeutic and toxic effects of Indocyanine green depend on the dose and duration of exposure. Indocyanine green has been shown to have a protective effect on the liver in low doses, but high doses can cause liver damage and toxicity.

Applications

Indocyanine green has various applications in medical research, environmental research, and industrial research. In medical research, Indocyanine green has been used as a contrast agent in medical imaging, such as fluorescence-guided surgery and optical coherence tomography. It has also been used in clinical trials for the diagnosis and treatment of various diseases, such as cancer, cardiovascular disease, and liver disease. The benefits of Indocyanine green in medical research include its high sensitivity and specificity, low toxicity, and rapid clearance from the body. However, potential side effects of Indocyanine green include allergic reactions, anaphylaxis, and liver toxicity.
In environmental research, Indocyanine green has been used to study the effects of pollutants on ecosystems and to monitor the sustainability and environmental impact of industrial processes. Indocyanine green has been shown to have a low toxicity to aquatic organisms and can be used as a marker for the detection of pollutants in water. In industrial research, Indocyanine green has been used in manufacturing processes to improve product quality and efficiency. It has also been used in health and safety considerations, such as the detection of leaks in pipelines and the monitoring of air quality in industrial settings.

Future Perspectives and Challenges

The current limitations in the use and study of Indocyanine green include its limited stability, low solubility, and high cost. Possible solutions and improvements include the development of new synthesis methods, the modification of the chemical structure of Indocyanine green to improve its stability and solubility, and the optimization of the purification process to increase the yield and purity of Indocyanine green. Future trends and prospects in the application of Indocyanine green in scientific research include the development of new diagnostic and therapeutic applications, such as targeted drug delivery and photodynamic therapy. The challenges in the application of Indocyanine green in scientific research include the need for further studies on its safety and efficacy, the development of new imaging techniques, and the optimization of the dose and duration of exposure.
Conclusion:
Indocyanine green is a versatile dye that has various applications in medical, environmental, and industrial research. Its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges have been discussed in this paper. Indocyanine green has shown great potential as a diagnostic and therapeutic tool in medical research, as well as a marker for the detection of pollutants in environmental research and a tool for improving product quality and efficiency in industrial research. However, further studies are needed to fully understand the safety and efficacy of Indocyanine green and to optimize its use in scientific research.

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