5-Aminolevulinic Acid Phosphate (CAS: 868074-65-1)

What is 5-Aminolevulinic Acid Phosphate

5-Aminolevulinic acid phosphate (5-ALP or 5-ALA phosphate) is an intermediate in heme biosynthesis, Its chemical appearance is white powder, and its CAS registration number is 868074-65-1.

Heme is a key component of hemoglobin, myoglobin, and cytochrome enzymes.

5-aminolevulinic acid phosphate is mainly used in the synthesis of heme, photodynamic therapy (PDT), and other fields.

5-Aminolevulinic Acid Phosphate Biological/Chemical Reaction

1. Biosynthesis of porphyrin ring:

The major biological reaction of 5-aminolevulinic acid phosphate (5-ALP) is its conversion to porphobilinogen, a key intermediate in heme biosynthesis. The principle is that two 5-aminolevulinic acid phosphate molecules condense to form a pyrrole ring.

2. Photodynamic therapy (PDT):

In photodynamic therapy (PDT), patients are administered 5-aminolevulinic acid (ALA) or a derivative thereof. These compounds are first taken up by rapidly dividing cells such as cancer cells. ALA or its derivatives are converted in cells to protoporphyrin IX (PpIX) when exposed to specific wavelengths of light, usually laser light. PpIX is a photosensitizer that generates reactive oxygen species when activated by light.

3. Heme biosynthesis pathway:

The conversion of 5-aminolevulinic acid phosphate to porphobilinogen is a key step in the heme biosynthetic pathway. The pathway continues with the addition of an additional pyrrole ring, leading to the formation of protoporphyrin IX (PpIX). PpIX further combines with iron to form heme.

4. Enzyme regulation:

5-aminolevulinic acid synthase (ALAS) catalyzes the conversion of 5-aminolevulinic acid phosphate to porpholinogen. This enzyme is regulated by a feedback mechanism based on the levels of heme and other intermediates in the pathway.

5. Potential metabolic disorders:

Imbalances in the heme biosynthetic pathway, including the production of 5-aminolevulinic acid phosphate, a metabolic disorder known as porphyria.

Uses of 5-Aminolevulinic Acid Phosphate

The uses of 5-aminolevulinic acid phosphate go beyond its role as a precursor for heme biosynthesis.

The following are its main applications:

1. Photodynamic Therapy (PDT): 5-aminolevulinic acid phosphate (5-ALP) is primarily used in photodynamic therapy (PDT). 5-ALP is used in PDT to treat certain types of skin cancer and precancerous lesions. When administered, these compounds are selectively taken up by cancer cells. When exposed to light of a specific wavelength, they are converted into protoporphyrin IX (PpIX) to generate reactive oxygen species. Reactive oxygen species can cause cell damage and induce apoptosis.
2. Research and Diagnostics: 5-ALP is widely used as a research tool in various biological studies and diagnostics. Can be used to study heme biosynthetic pathways, enzyme regulation, and metabolic disturbances associated with porphyrin metabolism. Researchers can manipulate levels of 5-ALP and its derivatives to study their effects on cellular processes and disease conditions.
3. Heme Biosynthesis Studies: 5-ALP is used to study the enzymatic steps involved in heme biosynthesis. Researchers can study the effect of modulating 5-ALP levels on the production of heme and related compounds.
4. Agricultural and horticultural applications: 5-ALP and its derivatives have been explored for their potential use in enhancing plant growth and stress resistance. Research is ongoing to determine their effectiveness in improving crop yield and quality.
5. Porphyrin production: 5-ALP is used in the synthesis of various porphyrin compounds. Porphyrins have a variety of applications in medicine, agriculture, and industry.
6. Drug delivery systems: Combined with conversion to PpIX upon illumination, 5-ALP has been explored as a potential component of drug delivery systems. The use of light-activated targeted release of therapeutic agents can provide localized therapy and reduce systemic side effects.

5-Aminolevulinic Acid Phosphate Preparation Method

The synthesis of 5-Aminolevulinic Acid Phosphate (5-ALP) involves several steps, typically starting from simple starting materials.

One common method for its preparation is through a series of enzymatic reactions that mimic the natural biosynthetic pathway.

Here is an outline of the general preparation method:

1. Starting Materials:

1. Succinyl-CoA: Provides the succinyl group needed for the synthesis of 5-ALP.
2. Glycine: Another starting material that contributes the amino group to the final molecule.

2. Enzymatic Reaction Steps:

The synthesis of 5-ALP involves several enzymatic steps that occur within cells. Here is a simplified overview of the key enzymatic reactions:

1. Condensation Reaction: Glycine and succinyl-CoA undergo a condensation reaction catalyzed by the enzyme 5-Aminolevulinic Acid Synthase (ALAS). This reaction results in the formation of 5-Aminolevulinic Acid (ALA).
2. Conversion to 5-Aminolevulinic Acid Phosphate: The generated 5-ALA is then converted into 5-Aminolevulinic Acid Phosphate (5-ALP) through a phosphorylation reaction. This step typically involves the addition of a phosphate group to the 5-ALA molecule.

3. Isolation and Purification:

Once the 5-ALP is synthesized, it can be isolated and purified through various techniques, including chromatography and crystallization.

It’s important to note that the actual synthesis of 5-ALP is more complex and involves specific enzymes, coenzymes, and cellular machinery. Therefore, it is not a simple matter to artificially synthesize 5-aminolevulinic acid phosphate. Natural Micron has many years of experience in manufacturing 5-aminolevulinic acid phosphate and can provide you with high-quality and pure 5-ALP. Contact us for free 5-ALP samples and technical support.

5-Aminolevulinic Acid Phosphate Safety and Risk

When considering the safety and risks of 5-aminolevulinic acid phosphate, it is important to consider its natural occurrence and its potential use as a therapeutic or diagnostic agent.

The following are the main contents about the safety and risks of 5-aminolevulinic acid phosphate

Safety:

1. Endogenous compounds: 5-ALP is a natural intermediate in the heme biosynthetic pathway.
2. Low Toxicity: 5-ALP is generally considered to have low toxicity in its natural environment in the body.

Risk:

1. Phototoxicity: When administered in the form of 5-ALA, especially when used in photodynamic therapy, patients may become photosensitized due to the accumulation of photosensitive molecules in tissues. This may cause the skin to react to light.
2. Local Irritation: In some cases, local skin irritation or reaction may occur at the site of administration of 5-ALA or its derivatives. This is usually mild and short-lived.
3. Individual Sensitivity: As with any compound, individual sensitivities and responses may vary. Some people may be more sensitive to the effects of 5-ALP or its derivatives.
4. INTERACTIONS: 5-ALA and its derivatives may interact with certain medications or medical conditions. It is important to disclose all medications and medical history to your healthcare provider before using 5-ALP-based products.

5-Aminolevulinic Acid Phosphate Research and Future Development

Research into 5-Aminolevulinic Acid Phosphate (5-ALP) continues to explore its various applications and potential future developments. Here are some areas of research and potential future directions for 5-ALP:

1. Photodynamic Therapy (PDT):

5-ALA, a derivative of 5-ALP, is currently used in PDT, a medical treatment that uses light-sensitive compounds to target and destroy cancer cells and other abnormal tissues. Research may focus on optimizing PDT protocols, enhancing its effectiveness, and expanding its use to treat different types of cancers and medical conditions.

2. Diagnosis and Imaging:

5-ALA is also used in fluorescence-guided surgery and diagnostics. Future research could explore the development of improved imaging techniques and diagnostic tools using 5-ALP or its derivatives. This could lead to more accurate and minimally invasive detection of various diseases.

3. Neurological Disorders:

5-ALP has shown potential in preclinical studies for the treatment of neurodegenerative disorders, such as Alzheimer’s disease and Parkinson’s disease. Further research may aim to understand its mechanisms of action, optimize dosing, and explore its neuroprotective effects.

4. Drug Delivery and Targeting:

Researchers are investigating the use of 5-ALP or its derivatives as carriers for drug delivery systems. This could include targeted drug delivery to specific tissues or cells, enhancing the therapeutic effect while minimizing side effects.

5. Agriculture and Plant Science:

5-ALP has been studied for its role in plant growth and stress responses. Future research might delve into its potential applications in agriculture, such as enhancing crop yields, improving stress tolerance, and promoting plant health.

6. Biotechnology and Synthetic Biology:

The biosynthesis of heme, in which 5-ALP is an intermediate, has relevance in biotechnology and synthetic biology. Researchers may explore the engineering of microbial systems to produce heme and related compounds for industrial and medical applications.

7. Therapeutic Agents:

Beyond PDT, 5-ALP or its derivatives might have broader therapeutic applications. Research may uncover novel uses, such as in anti-inflammatory treatments, antioxidants, or other therapeutic strategies.

8. Combination Therapies:

Future studies could investigate the potential synergistic effects of combining 5-ALP-based therapies with other treatments, such as chemotherapy, immunotherapy, or other targeted therapies.

9. Clinical Trials and Validation:

As research progresses, there may be more clinical trials evaluating the safety and efficacy of 5-ALP-based treatments for various medical conditions. These trials are essential for validating the potential benefits of 5-ALP in real-world medical settings.

It’s important to note that while these areas show promise, further research is needed to fully understand the potential of 5-ALP and its derivatives. As research progresses, the insights gained will contribute to the advancement of medical science and the development of innovative treatments and technologies.