Acide folique
Vue d'ensemble
Description
Folic acid, also known as pteroyl-L-glutamic acid, is a synthetic form of the naturally occurring B vitamin folate. It is essential for numerous bodily functions, including DNA synthesis, repair, and methylation, as well as amino acid metabolism. Folic acid is particularly important during periods of rapid cell division and growth, such as during pregnancy and infancy .
Mécanisme D'action
Target of Action
Folic acid, also known as folate or Vitamin B9, is an essential cofactor for enzymes involved in DNA and RNA synthesis . More specifically, folic acid is required by the body for the synthesis of purines, pyrimidines, and methionine before incorporation into DNA or protein . The primary targets of folic acid are the enzymes involved in these processes, including dihydrofolate reductase (DHFR) .
Mode of Action
In order to function within the body, folic acid must first be reduced by the enzyme DHFR into the cofactors dihydrofolate (DHF) and tetrahydrofolate (THF) . This is an important pathway required for de novo synthesis of nucleic acids and amino acids . Folic acid’s primary mechanisms of action are through its role as a one carbon donor . Folate helps in the transfer of a single methyl group in various metabolic reactions in the body and in the functioning of the nervous system . It is essential for DNA synthesis .
Biochemical Pathways
Folic acid participates in several biochemical pathways. It is necessary for the formation of a number of coenzymes in many metabolic systems, particularly for purine and pyrimidine synthesis . It is required for nucleoprotein synthesis and maintenance in erythropoiesis . Folic acid is also involved in the metabolism of formic acid, the toxic metabolite of methanol, to non-toxic metabolites .
Pharmacokinetics
Folic acid is absorbed in the proximal part of the small intestine . It is metabolized in the liver and excreted in the urine . The time to peak for oral administration is approximately 1 hour . As humans are unable to synthesize folic acid endogenously, diet and supplementation are necessary to prevent deficiencies .
Result of Action
Folic acid stimulates the production of red blood cells, white blood cells, and platelets in persons suffering from certain megaloblastic anemias . It is used to treat anemia caused by folate deficiency . Folic acid is also used as a supplement by women during pregnancy to reduce the risk of neural tube defects (NTDs) in the baby . Low levels in early pregnancy are believed to be the cause of more than half of babies born with NTDs .
Action Environment
The action of folic acid can be influenced by various environmental factors. For example, anti-metabolite therapies such as Methotrexate function as DHFR inhibitors to prevent DNA synthesis in rapidly dividing cells, and therefore prevent the formation of DHF and THF . When used in high doses such as for cancer therapy, or in low doses such as for Rheumatoid Arthritis or psoriasis, Methotrexate impedes the body’s ability to create folic acid . This results in a deficiency of coenzymes and a resultant buildup of toxic substances that are responsible for numerous adverse side effects . As a result, supplementation with 1-5mg of folic acid is recommended to prevent deficiency and a number of side effects associated with MTX therapy including mouth ulcers and gastrointestinal irritation .
Applications De Recherche Scientifique
Folic acid has a wide range of applications in scientific research:
Analyse Biochimique
Biochemical Properties
Folic acid is involved in several biochemical reactions as a cofactor. It is converted into its active form, tetrahydrofolic acid, which participates in one-carbon transfer reactions. These reactions are critical for the synthesis of purines and pyrimidines, which are the building blocks of DNA and RNA . Folic acid interacts with various enzymes, including dihydrofolate reductase, which reduces folic acid to dihydrofolate and then to tetrahydrofolate . It also interacts with methylenetetrahydrofolate reductase, which converts 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a key step in the remethylation of homocysteine to methionine .
Cellular Effects
Folic acid has significant effects on various types of cells and cellular processes. It is essential for the proper function of rapidly dividing cells, such as those in the bone marrow, gastrointestinal tract, and developing fetus . Folic acid influences cell function by participating in the synthesis of nucleotides, which are necessary for DNA replication and repair . It also affects cell signaling pathways and gene expression by providing methyl groups for DNA methylation, an epigenetic modification that regulates gene activity . Additionally, folic acid plays a role in cellular metabolism by facilitating the conversion of homocysteine to methionine, thereby reducing the levels of homocysteine, which is associated with cardiovascular diseases .
Molecular Mechanism
At the molecular level, folic acid exerts its effects through several mechanisms. It binds to and activates folate receptors on the cell surface, which facilitates its transport into the cell . Once inside the cell, folic acid is reduced to tetrahydrofolate by the enzyme dihydrofolate reductase . Tetrahydrofolate then participates in one-carbon transfer reactions, which are essential for the synthesis of nucleotides and amino acids . Folic acid also influences gene expression by providing methyl groups for DNA methylation, which can activate or repress specific genes . Additionally, folic acid can inhibit or activate certain enzymes, such as methylenetetrahydrofolate reductase, which plays a key role in homocysteine metabolism .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of folic acid can change over time. Folic acid is relatively stable under normal conditions, but it can degrade when exposed to high temperatures, light, or acidic environments . Long-term studies have shown that folic acid supplementation can have lasting effects on cellular function, including improved DNA synthesis and repair, reduced homocysteine levels, and enhanced cell proliferation . Excessive intake of folic acid over extended periods can lead to adverse effects, such as masking vitamin B12 deficiency and increasing the risk of certain cancers .
Dosage Effects in Animal Models
The effects of folic acid vary with different dosages in animal models. Low to moderate doses of folic acid have been shown to prevent neural tube defects and support normal growth and development . High doses of folic acid can lead to toxic effects, such as liver damage, impaired kidney function, and altered behavior . Studies in animal models have also demonstrated threshold effects, where a certain minimum dose of folic acid is required to achieve its beneficial effects . It is important to carefully monitor and adjust the dosage of folic acid to avoid potential adverse effects .
Metabolic Pathways
Folic acid is involved in several metabolic pathways, including the folate cycle and the methionine cycle . In the folate cycle, folic acid is converted to tetrahydrofolate, which then participates in one-carbon transfer reactions to synthesize nucleotides and amino acids . In the methionine cycle, folic acid provides methyl groups for the remethylation of homocysteine to methionine, which is essential for the synthesis of proteins and other biomolecules . Folic acid also interacts with various enzymes and cofactors, such as dihydrofolate reductase and methylenetetrahydrofolate reductase, to regulate these metabolic pathways .
Transport and Distribution
Folic acid is transported and distributed within cells and tissues through specific transporters and binding proteins . The primary transporters for folic acid are the reduced folate carrier and the proton-coupled folate transporter, which facilitate its uptake into cells . Once inside the cell, folic acid can bind to folate receptors and be transported to various cellular compartments, such as the nucleus and mitochondria . Folic acid can also accumulate in certain tissues, such as the liver and bone marrow, where it is stored and utilized as needed .
Subcellular Localization
The subcellular localization of folic acid is critical for its activity and function. Folic acid is primarily localized in the cytoplasm, where it participates in one-carbon transfer reactions and nucleotide synthesis . It can also be transported to the nucleus, where it provides methyl groups for DNA methylation and gene regulation . Additionally, folic acid can be found in the mitochondria, where it supports the synthesis of mitochondrial DNA and proteins . The localization of folic acid is regulated by specific targeting signals and post-translational modifications that direct it to the appropriate cellular compartments .
Méthodes De Préparation
Synthetic Routes and Reaction Conditions: Folic acid is synthesized through a multi-step chemical process. The synthesis begins with the condensation of p-aminobenzoic acid with glutamic acid, followed by the addition of a pteridine ring. The reaction conditions typically involve acidic or basic environments to facilitate the formation of the desired product .
Industrial Production Methods: In industrial settings, folic acid is produced using large-scale chemical synthesis. The process involves the use of high-pressure reactors and controlled temperature conditions to ensure high yield and purity. The final product is then purified through crystallization and filtration techniques .
Analyse Des Réactions Chimiques
Types of Reactions: Folic acid undergoes various chemical reactions, including oxidation, reduction, and substitution.
Common Reagents and Conditions:
Reduction: Reduction reactions typically involve the use of reducing agents such as zinc powder in acidic conditions.
Substitution: Substitution reactions may involve the replacement of functional groups on the pteridine ring or the glutamic acid moiety.
Major Products Formed: The major products formed from these reactions include dihydrofolate and tetrahydrofolate, which are crucial intermediates in various metabolic pathways .
Comparaison Avec Des Composés Similaires
Tetrahydrofolate: The active form of folic acid, involved in one-carbon metabolism.
5-Methyltetrahydrofolate: A naturally occurring form of folate with higher bioavailability
Comparison: Folic acid is more stable and has a longer shelf life compared to its naturally occurring counterparts. it requires conversion to its active form in the body, whereas 5-methyltetrahydrofolate is readily available for use .
Folic acid’s stability and ease of production make it a preferred choice for food fortification and supplements, ensuring that populations receive adequate amounts of this vital nutrient .
Propriétés
IUPAC Name |
(2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
OVBPIULPVIDEAO-LBPRGKRZSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1=CC(=CC=C1C(=O)NC(CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=O)NC(=N3)N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
C1=CC(=CC=C1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=O)NC(=N3)N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C19H19N7O6 |
Source
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| Record name | FOLIC ACID | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20419 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
36653-55-1 (mono-potassium salt), 6484-89-5 (mono-hydrochloride salt) |
Source
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| Record name | Folic acid [USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000059303 | |
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DSSTOX Substance ID |
DTXSID0022519 |
Source
|
| Record name | Folic acid | |
| Source | EPA DSSTox | |
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Molecular Weight |
441.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Folic acid appears as odorless orange-yellow needles or platelets. Darkens and chars from approximately 482 °F., Yellowish-orange solid; [Merck Index] Yellow solid; [Sigma-Aldrich MSDS], Solid |
Source
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| Record name | FOLIC ACID | |
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| Record name | Folic acid | |
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| Record name | Folic acid | |
| Source | Human Metabolome Database (HMDB) | |
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Solubility |
Almost insoluble (NTP, 1992), Slightly sol in methanol, less in ethanol and butanol; insol in acetone, chloroform, ether, benzene; relatively sol in acetic acid, phenol, pyridine, and in soln of alkali hydroxides and carbonates. Soluble in hot dil HCl and H2SO4., In water, 1.6 mg/L at 25 °C; soluble up to about 1% in boiling water, 0.0016 mg/mL |
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| Record name | FOLIC ACID | |
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| Record name | Folic acid | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0000121 | |
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Vapor Pressure |
6.2X10-20 mm Hg at 25 °C /Estimated/ |
Source
|
| Record name | FOLIC ACID | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/2002 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Mechanism of Action |
Folic acid, as it is biochemically inactive, is converted to tetrahydrofolic acid and methyltetrahydrofolate by dihydrofolate reductase (DHFR). These folic acid congeners are transported across cells by receptor-mediated endocytosis where they are needed to maintain normal erythropoiesis, synthesize purine and thymidylate nucleic acids, interconvert amino acids, methylate tRNA, and generate and use formate. Using vitamin B12 as a cofactor, folic acid can normalize high homocysteine levels by remethylation of homocysteine to methionine via methionine synthetase., Folic acid, after conversion to tetrahydrofolic acid, is necessary for normal erythropoiesis, synthesis of purine and thymidylates, metabolism of amino acids such as glycine and methionine, and the metabolism of histidine., The principal biochemical function of folates is the mediation of one-carbon transfer reactions. 5-Methyltetrahydrofolate donates a methyl group to homocystine, in the conversion of homocystine to L-methionine. ... 5,10-Methyltetrahydrofolate is regenerated from tetrahydrofolate via the enzyme serine hydroxymethyltransferase, a reaction, which in addition to producing 5,10-methyltetrahydrofolate, yields glycine. ... 5,10-methyltetrahydrofolate, supplies the one carbon group for the methylation of deoxyuridylic acid to form the DNA precursor thymidylic acid. This reaction is catalyzed by thymidylate synthase and the folate product of the reaction is dihydrofolate. Dihydrofolate is converted to tetrahydrofolate via the enzyme dihydrofolate reductase ... |
Source
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| Record name | Folic acid | |
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Color/Form |
Yellowish-orange crystals; extremely thin platelets (elongated @ 2 ends) from hot water | |
CAS No. |
59-30-3 |
Source
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| Record name | FOLIC ACID | |
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| Record name | Folic acid [USP:INN:BAN:JAN] | |
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| Record name | L-Glutamic acid, N-[4-[[(2-amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]- | |
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Melting Point |
482 °F (decomposes) (NTP, 1992), 250 °C |
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| Record name | FOLIC ACID | |
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| Record name | Folic acid | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0000121 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
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Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Q1: How does folic acid contribute to preventing neural tube defects (NTDs)?
A: Folic acid plays a crucial role in the synthesis of purines and pyrimidines, which are essential building blocks for DNA and RNA. [] This is particularly critical during periods of rapid cell division and growth, such as during fetal development. Insufficient folic acid during the periconceptional period (the time just before and after conception) can disrupt the closure of the neural tube, leading to NTDs like spina bifida and anencephaly. []
Q2: What is the molecular formula and weight of folic acid?
A: Folic acid has the molecular formula C19H19N7O6 and a molecular weight of 441.40 g/mol. [, ]
Q3: Is there a link between folic acid levels and preeclampsia?
A: Research suggests that lower folic acid levels in placental tissue are associated with preeclampsia development. [] In vitro studies have shown that folic acid supplementation can enhance the invasive potential of placental trophoblasts, potentially offering a protective effect against preeclampsia. []
Q4: Can folic acid supplementation affect cognitive function?
A: While folic acid is crucial for central nervous system development, research on its cognitive benefits in elderly individuals with or without dementia has yielded mixed results. [] Some studies found no significant improvement in cognitive function with folic acid supplementation, while others reported potential negative effects with high doses. []
Q5: Are there concerns regarding the safety of folic acid supplementation?
A: While generally considered safe, excessive folic acid intake, particularly from supplements, can lead to high levels of unmetabolized folic acid in the blood. [] The long-term effects of this are not fully understood, and some studies suggest potential associations with adverse health outcomes. [, ] One concern is the potential for masking vitamin B12 deficiency, which can have serious neurological consequences. [, , ]
Q6: How do anticonvulsant drugs affect folic acid levels?
A: Studies have shown an association between anticonvulsant drug therapy and lower serum folate levels, sometimes leading to megaloblastic anemia. [] The mechanism is thought to involve interference with folate metabolism, potentially through a weak antagonistic effect. []
Q7: How are folic acid levels measured in biological samples?
A: Various analytical methods are used to measure folic acid levels, including microbiological assays using Lactobacillus casei and chemiluminescence methods. [, ] Researchers have also developed methods to measure folic acid absorption using radiolabeled folic acid (3H-folic acid). []
Q8: What are the challenges in studying folic acid deficiency?
A: Studying chronic folic acid deficiency can be challenging due to the ethical considerations of inducing deficiency in humans. [] Animal models, such as rats fed specific diets, have been used to study the effects of folic acid deficiency. []
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