Pristane, also known as 2,6,10,14-tetramethylpentadecane, is a naturally occurring branched-chain alkane hydrocarbon. It is commonly found in shark liver oil and certain microorganisms, playing roles in biological systems as a metabolic byproduct or energy reserve. Structurally, it consists of a 15-carbon backbone with four methyl branches, imparting unique chemical properties.
In research, it is notable for its use in animal models to induce autoimmune diseases like lupus and arthritis. Its hydrophobic nature triggers immune responses, mimicking human autoimmune conditions, thus aiding in therapeutic development. Additionally, it serves as a solvent in organic chemistry due to its stability and low reactivity. It is utilized in the synthesis of specialized polymers and as a reference compound in chromatographic analyses.
Environmentally, it is a component of petroleum and can persist in ecosystems, influencing microbial degradation pathways. Its presence in sediment or water may indicate hydrocarbon contamination. Despite its potential environmental impact, the biological and chemical versatility continues to drive interest in fields ranging from medicine to materials science. Its dual role as a research tool and industrial compound underscores its significance in both laboratory and applied contexts.
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Chemical Formula |
C19H40 |
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Exact Mass |
268.31 |
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Molecular Weight |
268.53 |
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m/z |
268.31 (100.0%), 269.32 (20.5%), 270.32 (2.0%) |
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Elemental Analysis |
C, 84.98; H, 15.02 |
Induction of Autoimmune Disease Models
Systemic Lupus Erythematosus (SLE) Model
Autoimmune Reaction Trigger: Pristane acts as a potent inducer of autoimmune responses by stimulating the immune system in a non-specific manner. It leads to the production of autoantibodies, particularly antinuclear antibodies (ANAs), which are hallmarks of SLE in humans. These autoantibodies can target various cellular components, leading to tissue damage and inflammation.
Interferon Signaling Abnormalities: One of the key features of pristane-induced SLE models is the dysregulation of interferon signaling pathways. Interferons are cytokines that play a crucial role in the immune response, and their overproduction or abnormal signaling can contribute to the pathogenesis of SLE. It treatment results in elevated levels of type I interferons, mimicking the interferon signature observed in many SLE patients.
Organ Damage and Antibody Characteristics: The autoimmune reactions and interferon signaling abnormalities induced by it lead to organ damage, particularly affecting the kidneys (nephritis) and joints (arthritis), which are common manifestations of SLE. The antibody profile generated in pristane-treated mice closely resembles that of human SLE patients, making it a relevant model for studying the disease.
Significance in Disease Mechanism Exploration
Understanding Pathogenesis: By inducing SLE-like symptoms in mice, it allows researchers to investigate the underlying mechanisms of the disease. This includes studying the role of genetic factors, immune cell interactions, and cytokine networks in the development and progression of SLE.
Role of Environmental Factors: As an environmental agent, highlights the potential impact of exogenous factors on the development of autoimmune diseases. This is particularly relevant given that SLE is thought to result from a combination of genetic predisposition and environmental triggers.
Therapeutic Target Identification: The pristane-induced SLE model provides a platform for testing potential therapeutic interventions. Researchers can evaluate the efficacy of new drugs or treatment strategies in ameliorating disease symptoms and preventing organ damage.
Experimental Methodology
Intraperitoneal Injection: The standard method for inducing SLE in mice involves the intraperitoneal injection. This route of administration ensures that it is distributed throughout the peritoneal cavity, where it can interact with immune cells and trigger the autoimmune response. The dose and timing of injection can be adjusted to modulate the severity and progression of the disease in the model.
Limitations and Considerations
While the pristane-induced SLE model is a valuable tool, it is important to recognize its limitations. The model does not fully replicate all aspects of human SLE, such as the gender bias (female predominance) and the chronicity of the disease. Therefore, researchers often use it in conjunction with other models to obtain a more comprehensive understanding of SLE. Additionally, the use of animal models raises ethical considerations, and efforts should be made to minimize animal suffering and ensure the humane treatment of research subjects.
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Arthritis Model
Mechanism of Action as a Non-Antigenic Adjuvant
Induction of Arthritogenic T Cells: It has the unique ability to induce MHC class II-restricted arthritogenic T cells in rats. These T cells are pivotal in the immune response that leads to arthritis. By stimulating the production of these specific T cells, it sets off a cascade of immune reactions that culminate in joint inflammation and damage, mirroring the processes observed in human arthritis.
Non-Antigenic Nature: Unlike traditional adjuvants that rely on antigen-specific responses, it acts in a non-antigenic manner. This means it can induce an immune response without the need for a specific foreign antigen. This property makes it particularly useful for studying the immune system's role in arthritis, as it allows researchers to isolate and examine the effects of the adjuvant itself on immune cell activation and inflammation.
Application in Arthritis Models
Model Induction: The administration to rats is a well-established method for inducing arthritis models. Typically, pristane is injected intraperitoneally, where it interacts with the immune system to trigger the production of arthritogenic T cells and subsequent joint inflammation. This model closely resembles the clinical features of human arthritis, including joint swelling, pain, and cartilage destruction.
Facilitating Pathogenesis Research: By providing a controlled environment for studying arthritis, the pristane-induced arthritis model allows researchers to investigate the underlying mechanisms of the disease. This includes examining the role of immune cells, cytokines, and signaling pathways in the development and progression of arthritis. Understanding these mechanisms is crucial for identifying new therapeutic targets and developing more effective treatments.
Evaluation of Potential Therapies: The pristane-induced arthritis model also serves as a valuable tool for evaluating the efficacy of potential therapies. Researchers can test new drugs or treatment strategies in the model to assess their ability to reduce joint inflammation, prevent cartilage destruction, and improve overall joint function. This preclinical testing is essential for determining the safety and effectiveness of new therapies before they are tested in human clinical trials.
Significance and Implications
- Advancing Arthritis Research: The use in arthritis models has significantly advanced our understanding of the disease. It has helped identify key immune cells and signaling pathways involved in arthritis pathogenesis, leading to the development of new therapeutic strategies.
- Translational Research: The insights gained from pristane-induced arthritis models can be translated into clinical practice. By understanding the mechanisms of arthritis in the model, researchers can develop more targeted and effective therapies for human patients.
- Ethical Considerations: While the use of animal models is essential for arthritis research, it is important to consider ethical implications. Researchers must ensure that animals are treated humanely and that experiments are conducted in accordance with ethical guidelines. Efforts should also be made to minimize animal suffering and reduce the number of animals used in experiments.
Pristane, also known as 2,6,10,14-tetramethylpentadecane or Norphytane, is a naturally occurring saturated terpenoid alkane. Its research history is closely tied to its diverse applications in scientific and medical fields.
Initially, it was recognized for its presence in shark liver oil and certain marine organisms. Its unique chemical structure and properties led researchers to explore its potential uses. One of the earliest and most significant applications was in the induction of autoimmune diseases in animal models. In the late 20th century, it emerged as a powerful tool for studying the pathogenesis of systemic lupus erythematosus (SLE) and rheumatoid arthritis (RA). By triggering immune responses in mice and rats, it mimics the organ damage and antibody profiles observed in human SLE, providing valuable insights into the disease mechanisms and the role of environmental factors.
Over the years, it has been extensively studied for its role in immune modulation. It has been shown to activate innate immune cells, such as dendritic cells and macrophages, leading to the overproduction of type I interferons, which is a hallmark of SLE. This discovery has further solidified the position as a key research reagent in autoimmune disease studies.
In addition to its use in autoimmune disease models, pristane has also been investigated for its potential as an adjuvant in vaccine development and as a solvent in organic chemistry. Its versatility and stability have made it a valuable compound in various research settings.
As research continues, the role in understanding and treating autoimmune diseases remains crucial. Its ability to induce disease-like symptoms in animal models provides a controlled environment for testing new therapies and exploring the complex interplay between genetics and the environment in disease development.
Pristane (2,6,10,14-tetramethylpentadecane, C19H40), as a typical isoprenoid alkane, has been discovered across multiple fields including organic chemistry, marine biology, petroleum geology, and immunomedicine. This compound, originally isolated from shark liver, has now become a key indicator molecule in biogeochemical cycling research.
In 1875, German chemist Heinrich Hlasiwetz first noticed a high boiling neutral component that could not be saponified while analyzing the liver oil of deep-sea sharks (Centrophorus squamosus). Early literature referred to it as' Selacyl alcohol ', but later it was confirmed to be an oxidized derivative of Pristane.
In 1926, Leopold Ruzicka's team at the Swiss Federal Institute of Technology in Zurich determined through ozone decomposition experiments that its carbon skeleton was composed of regular methyl branched alkanes. Its name comes from the Latin word "pristis" (shark) and was officially named by French chemist Marcel Guerbet.
In 1953, American chemist John D. Roberts utilized the isoprene rule to achieve the total synthesis of Pristane for the first time through hydrogenation/coupling of Farnesol.
In 1967, NMR technology confirmed that natural Pristane was in an all trans configuration.
In 1969, a British team discovered that chlorophyll side chains (Phytol) were degraded by anaerobic bacteria to produce Pristane. The Pristane/Phytone ratio in sedimentary rocks has become a paleoenvironmental indicator.
In 1974, the National Institutes of Health (NIH) in the United States discovered that Pristane could induce mouse plasma cell tumors while screening mineral oil substitutes, becoming a key reagent for autoimmune disease models.
In 1991, it was confirmed that it stimulates B cell proliferation by activating the TLR4/MyD88 pathway.
In the 1980s, the Pristane/n-C17 ratio was widely used to evaluate the degree of thermal evolution of crude oil. The ratio to phytane indicates the type of original producer.
In 2016, the JBEI Institute in the United States achieved microbial synthesis of Pristane by modifying Escherichia coli. Its high cetane number (>80) has sparked a research boom in bio aviation coal.
In 2021, the European Union's ECHA classified Pristane as a Class 2 carcinogen and restricted its use as an adjuvant.
Frequently Asked Questions
What is pristane used for?
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Pristane and phytane are used in the fields of geology and environmental science as biomarkers to characterize origins and evolution of petroleum hydrocarbons and coal. Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
How does pristane induce lupus?
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Pristane, known as a membrane-activating compound, can induce apoptosis in peripheral tissues and produce sufficient autoantigen substrates for immune intolerance, which can lead to overproduction of cytokines and the development of lupus-like autoimmunity.
What is pristane and phytane?
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Pristane and phytane are common constituents in petroleum and have been used as proxies for depositional redox conditions, as well as for correlating oil and its source rock (i.e. elucidating where oil formed). In environmental studies, pristane and phytane are target compounds for investigating oil spills.
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