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The CAS number of sapropterin dihydrochloride powder is 69056-38-8, the EINECS number is 663-669-3, the molecular formula is C9H17Cl2N5O3, and the molecular weight is 314.17. Usually presented as a white to off white powdery solid. It has a high solubility in water, especially under anaerobic conditions, with a solubility of 19.60-20.40 mg/mL. The solution is clear to slightly turbid, colorless to pale yellow. This good water solubility makes the absorption and utilization of the compound in organisms more efficient. As a cofactor of phenylalanine hydroxylase, it can increase enzyme activity, promote phenylalanine metabolism, thereby reducing serum phenylalanine levels and improving neurological symptoms in patients. Therefore, it is used to treat phenylketonuria, especially for BH4 reactive PKU patients, with significant effects. As an important biochemical reagent and drug precursor, it has a wide range of applications in drug research. It can be used for synthesizing new drug molecules, screening drug targets, evaluating drug efficacy, and more. By studying this substance, we can gain a deeper understanding of the structure and function of related enzymes, as well as their mechanisms of action in disease occurrence and development.
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Chemical Formula |
C9H15N5O3 |
|
Exact Mass |
241.12 |
|
Molecular Weight |
241.25 |
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m/z |
241.12 (100.0%), 242.12 (9.7%), 242.11 (1.8%) |
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Elemental Analysis |
C, 44.81; H, 6.27; N, 29.03; O, 19.9 |
Related information of Sapropterin dihydrochloride. Sulfasalazine and its metabolites SULFAPYRIDINE and mesalazine are inhibitors of enzymes that catalyze the last step of the biosynthesis of cofactor tetrahydrobiopterin. The interference of tetrahydrobiopterin metabolism provides an explanation for some beneficial and harmful properties of sulfasalazine, and further puts forward new and improved therapies for the drug.
Sapropterin dihydrochloride powder has multiple important functions in the field of scientific research. As a biochemical tool, it is widely used in various aspects of life sciences and medical research.
1. Treatment of phenylketonuria (PKU)
Phenylketonuria is a genetic disease caused by a deficiency of phenylalanine hydroxylase, in which phenylalanine cannot be converted to tyrosine in the patient's body, leading to the accumulation of phenylalanine and its metabolites in the body and causing neurological damage.
Sapropterin Hydrochloride, as a cofactor of phenylalanine hydroxylase, can increase enzyme activity, promote phenylalanine metabolism, thereby reducing serum phenylalanine levels and improving neurological symptoms in patients. Therefore, Sapropterin Hydrochloride is used to treat phenylketonuria, especially for BH4 reactive PKU patients, with significant efficacy.
2. Treatment of tetrahydrobiopterin deficiency (BH4D)
Tetrahydrobiopterin deficiency is a rare genetic disease caused by impaired synthesis or regeneration of tetrahydrobiopterin, resulting in decreased activity of various enzymes (including phenylalanine hydroxylase, tyrosine hydroxylase, etc.), leading to symptoms such as hyperphenylalaninemia and insufficient dopamine synthesis.
Sapropterin Hydrochloride, as an exogenous tetrahydrobiopterin supplement, can directly replace the missing tetrahydrobiopterin in the body, restore the activity of related enzymes, and improve patients' symptoms. Therefore, Sapropterin Hydrochloride is an effective drug for treating tetrahydrobiopterin deficiency.
3. Neuroprotective effect
Research has shown that Sapropterin Hydrochloride has neuroprotective effects. It can increase the synthesis and release of nitric oxide in the brain, improve the vasodilation function of cerebral blood vessels, and protect neurons from damage such as hypoxia and ischemia. In addition, Sapropterin Hydrochloride can promote the synthesis and release of neurotransmitters, regulating the function of the nervous system.
4. Antioxidant effect
Sapropterin Hydrochloride also has certain antioxidant properties. It can eliminate harmful substances such as free radicals and peroxides in the body, reducing oxidative stress damage to cells. This is of great significance for the prevention and treatment of diseases related to oxidative stress.
Pharmacological applications
1. Drug research
Sapropterin Hydrochloride, as an important biochemical reagent and drug precursor, has a wide range of applications in drug research. It can be used for synthesizing new drug molecules, screening drug targets, evaluating drug efficacy, and more. By studying Sapropterin Hydrochloride, we can gain a deeper understanding of the structure and function of related enzymes, as well as their mechanisms of action in disease occurrence and development.
2. Drug metabolism research
Sapropterin Hydrochloride can also be used for drug metabolism research. It can serve as a probe molecule for monitoring the metabolic processes, metabolites, and interactions between drugs and enzymes in the body. This is of great significance for optimizing drug structure, improving drug efficacy, and reducing drug side effects.
1. Nutritional supplements
Although sapropterin dihydrochloride powder is primarily used to treat specific diseases, it can also be used as a nutritional supplement in certain situations. For example, in some patients with genetic diseases, when the synthesis or utilization of tetrahydrobiopterin in the body is insufficient, leading to a deficiency of related nutrients, Sapropterin Hydrochloride can be supplemented appropriately to meet the body's needs.
2. Research tools
It is also commonly used as a research tool in biochemistry and molecular biology research. It can be used to study the structure and function of related enzymes, the regulatory mechanisms of metabolic pathways, and the molecular mechanisms of disease occurrence and development. By using Sapropterin Hydrochloride as a probe or marker for research, the intrinsic laws and mechanisms of many biological phenomena can be revealed.
In addition to the above purposes, it has a wide range of application value as a research tool in various fields such as biochemistry, molecular biology, drug development and screening.
Biochemical Research
1. Research on Enzymatic Reactions
It is a cofactor of various key enzymes, including phenylalanine hydroxylase (PAH), tyrosine hydroxylase (TH), etc. In biochemical research, it is often used to study the catalytic mechanism, substrate specificity, and cofactor dependence of these enzymes. By changing the concentration or structure of Sapropterin Hydrochloride, changes in enzyme activity can be observed, revealing the interaction mechanism between enzymes and co factors.
2. Metabolic pathway analysis
Participate in the metabolic pathways of amino acids such as phenylalanine and tyrosine. In scientific research, it is often used to study the regulatory mechanisms of these metabolic pathways, the generation and transformation of metabolites, and the mechanisms of metabolic diseases. Through isotope labeling, metabolomics, and other methods, it is possible to track the flow and changes in metabolic pathways, providing important information for a deeper understanding of metabolic processes.
Molecular Biology Research
1. Gene expression and regulation
Lack of association with various genetic metabolic diseases, the occurrence of which is often related to mutations or abnormal expression of specific genes. In molecular biology research, sapropterin dihydrochloride powder is often used to study the expression patterns, regulatory mechanisms, and relationships between genes and phenotypes of related genes. Through techniques such as gene knockout, gene overexpression, and RNA interference, the impact on gene expression can be observed, revealing its mechanism of action in genetic metabolic diseases.
2. Protein Structure and Function
As a cofactor of enzymes, the binding with enzyme proteins is crucial for the catalytic activity of enzymes. In the study of protein structure and function, it is often used to investigate the binding mechanism between enzyme proteins and cofactors, the structural characteristics of binding sites, and the impact of binding on enzyme activity. By using structural biology techniques such as X-ray crystallography and nuclear magnetic resonance, the complex structure between enzyme proteins and Sapropterin Hydrochloride can be analyzed, providing important information for a deeper understanding of the catalytic mechanism of enzymes.
Drug Development And Screening
1. Drug target discovery
As a drug for treating genetic metabolic diseases, its target is key enzymes in related metabolic pathways. In drug development, it is often used as a model compound or probe molecule to discover new drug targets or validate the effectiveness of known targets. By constructing a complex model of target proteins and Sapropterin Hydrochloride, the binding mode and affinity between drugs and targets can be predicted, providing important basis for drug design.
2. Drug screening and evaluation
As a drug with known therapeutic effects, its pharmacological mechanism of action is clear and distinct. In drug screening and evaluation, it is often used as a positive control drug or reference drug to evaluate the efficacy and safety of newly developed drugs. By comparing the performance differences of new drugs with in vitro experiments or animal models, the potential value and application prospects of new drugs can be preliminarily judged.
It can also be used in fields such as cell culture and cell biology research. In cell culture, it can serve as one of the essential factors for cell growth and metabolism; In cell biology research, it can be used to study the process of cellular uptake and utilization of nutrients such as amino acids, as well as the regulatory mechanisms of cellular metabolic pathways.
Regarding the synthesis route of 2-amino-6- (2 '- hydroxyphenyl) -4- (2' - hydroxyethyl) -5,6,7,8-tetrahydrodipyrimidine (assuming the structure of Sapropterin or its analogues, but please note that the exact structure of Sapropterin may be slightly different and is not directly referred to as "tetrahydrodipyrimidine") and the detailed steps and chemical equations for its conversion to Sapropterin dihydrochloride powder, due to differences in laboratory conditions, raw material availability, and optimization strategies, the following is a hypothetical description based on general principles of organic synthesis.
Overview of synthetic routes
The synthesis of 2-amino-6- (2 '- hydroxyphenyl) -4- (2' - hydroxyethyl) -5,6,7,8-tetrahydrodipyrimidine (hypothetical structure) typically involves multiple steps, including the selection of starting materials, the synthesis of key intermediates, and the final cyclization reaction. Due to the impracticality of providing detailed synthesis steps and chemical equations up to 2000 words, I will outline a possible synthesis route and point out the key points of each step.
Synthesis steps and chemical equations (hypothetical)
Step 1: Select appropriate starting materials, such as compounds containing phenol rings and amino groups as one part, and compounds containing hydroxyl and carbonyl groups as the other part. These raw materials may need to be obtained through commercial purchase or pre synthesis.
Step 2: Combine compounds containing phenol rings with compounds containing hydroxyl and carbonyl groups through condensation reactions (such as Mannich reaction or similar reactions) to form intermediates containing the target moiety structure. This step may require a catalyst and appropriate solvent.
Example of chemical equation (hypothetical):
Phenolic compounds+hydroxycarbonyl compounds → intermediates
Step 3: Perform further functional group conversion on the intermediate, such as reduction, oxidation, acylation, etc., to introduce or modify the desired functional groups. These steps may involve multiple reactions, each requiring precise control of reaction conditions and reagent dosage.
Step 4: Transform the intermediate into the target compound through cyclization reaction. This is usually a critical step that requires selecting appropriate cyclization reagents and conditions. The cyclization reaction may involve heating, catalysts, or strong acid/base conditions.
Example of chemical equation (hypothetical):
Intermediate → 2-amino-6- (2 '- hydroxyphenyl) -4- (2' - hydroxyethyl) -5,6,7,8-tetrahydrodipyrimidine
Step 5: Purify the target compound through column chromatography, recrystallization, or other purification techniques to remove impurities. The purified compound needs to undergo structural characterization, such as NMR, IR, MS, etc., to confirm its structure.
Step 6 (hypothetical): If the target compound is not Sapropterin itself, but its analog, further transformation steps are required. However, for the direct synthesis of Sapropterin Hydrochloride, it is usually not necessary to start from the assumed compounds mentioned above. But for the completeness of the answer, we can assume that there is a step to convert the target compound into Sapropterin, followed by acidification to obtain its hydrochloride salt.
Chemical equation example (highly hypothetical):
Target compound → Sapropterin+HCl → Sapropterin Hydrochloride
It should be noted that the above conversion steps and chemical equations are highly hypothetical, as the specific synthesis route of Sapropterin may involve complex organic synthesis strategies and usually do not directly start from the assumed 2-amino-6- (2 '- hydroxyphenyl) -4- (2' - hydroxyethyl) -5,6,7,8-tetrahydrodipyrimidine structure.
In addition, due to the important physiological functions of Sapropterin in living organisms, and its synthesis often closely linked to in-depth research in biochemistry and medicinal chemistry, its synthesis route is usually carefully designed and optimized. The following is a more realistic overview of its synthesis route, although it still cannot go into detail for each chemical equation, it will provide more specific steps and ideas.
Overview of synthetic routes
1. Preparation of precursor compounds
The synthesis of Sapropterin typically begins with one or more relatively simple compounds, which are referred to as precursor compounds. These precursor compounds may include molecules containing functional groups such as benzene rings, amino groups, hydroxyl groups, and carbonyl groups. Through a series of organic reactions such as acylation, alkylation, reduction, oxidation, etc., the skeleton structure of Sapropterin is gradually constructed.
2. Formation of key intermediates
During the synthesis process, a series of key intermediates are formed, which serve as bridges between the starting materials and the target product. The selection and design of these intermediates are crucial for the success of the entire synthetic route. For example, it may be necessary to form the unique tetrahydropyridine or pyridine ring structure of Sapropterin through Diels Alder reaction, Pictet Spengler reaction, or other cyclization reactions.
3. Stereochemical control
Sapropterin is a compound with a specific stereoconfiguration, so strict control of reaction conditions is required during the synthesis process to ensure the generation of intermediates and target products with the correct stereoconfiguration. This typically involves the use of chiral catalysts, chiral reagents, or asymmetric synthesis reactions.
4. Post processing and purification
The synthesized crude Sapropterin needs to undergo post-processing and purification steps to remove impurities and improve the purity of the product. These steps may include extraction, washing, drying, crystallization, column chromatography, etc. The purified Sapropterin needs further structural characterization to confirm its chemical structure and purity.
5. Convert to Sapropterin Hydrochloride
The purified Sapropterin can be converted into its hydrochloride form by reacting with hydrochloric acid. This step typically involves dissolving Sapropterin in a suitable solvent, then slowly adding hydrochloric acid, while controlling the reaction temperature and stirring speed to ensure the formation of stable Sapropterin Hydrochloride salt.
6. Quality control and stability testing
Finally, the synthesis of e requires quality control and stability testing to ensure that sapropterin dihydrochloride powder meets pharmacopoeial standards and can maintain stability during storage and use. These tests may include content determination, impurity inspection, microbial limit inspection, stability testing, etc.
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