5-Aminolevulinic Acid Hydrochloride (CAS: 5451-09-2)

What is 5-Aminolevulinic Acid Hydrochloride (5-ALA HCl)?

5-Aminolevulinic Acid Hydrochloride (5-Aminolevulinic acid HCl) is a pharmaceutical compound that plays a crucial role in the biosynthesis of heme. As a chemical raw material, the appearance is a white powder. Its CAS registration number is 5451-09-2.

Heme is a critical molecule involved in oxygen transport, energy production, and various enzymatic processes. it is a prosthetic group found in hemoglobin, myoglobin, and cytochromes.

In addition to being used to synthesize heme, 5-aminolevulinic acid hydrochloride is also one of the very important chemicals in photodynamic therapy and tumor imaging.

5-Aminolevulinic acid HCl Biological/Chemical Reaction

1. Heme Biosynthesis:

In the first step of the heme biosynthesis pathway, 5-Aminolevulinic Acid (5-ALA) is produced from succinyl-CoA and glycine in the mitochondria. This reaction is catalyzed by the enzyme ALA synthase.

2. Conversion to Porphobilinogen:

5-ALA is further converted into porphobilinogen through a series of enzymatic reactions in the cytoplasm.

3. Photodynamic Therapy (PDT) Activation:

5-ALA HCl is administered to patients for photodynamic therapy. It is absorbed by cells and converted into protoporphyrin IX (PpIX) through a series of enzymatic reactions in the heme biosynthesis pathway.

4. Tumor Imaging and Detection:

In cancer diagnosis and surgery, 5-ALA HCl is administered to induce the production of PpIX in tumor cells. PpIX emits fluorescent light when exposed to specific wavelengths of light.

5. Enzymatic Regulation:

The conversion of 5-ALA to PpIX involves several enzymes, including ALA dehydratase and ferrochelatase. The regulation of these enzymes plays a critical role in maintaining the balance between heme synthesis and PpIX accumulation.

6. Photosensitizer Role:

5-Aminolevulinic Acid Hydrochloride acts as a photosensitizer in photodynamic therapy. Its ability to generate reactive oxygen species upon light activation makes it a valuable tool in cancer treatment.

Uses of Aminolevulinic Acid Hydrochloride

1. Photodynamic Therapy (PDT) for Cancer:

One of the primary uses of 5-Aminolevulinic Acid Hydrochloride (5-ALA HCl) is in photodynamic therapy (PDT) for various types of cancers. Patients are administered 5-ALA HCl, which is metabolized by cells into protoporphyrin IX (PpIX). When exposed to specific wavelengths of light, PpIX generates reactive oxygen species (ROS), causing oxidative damage to cancer cells and inducing their destruction.

2. Detection and Visualization of Tumors:

5-ALA HCl is used for tumor detection and visualization during surgery. When administered, it selectively accumulates in cancer cells, leading to the production of PpIX. During surgery, PpIX emits fluorescence when illuminated with specific light wavelengths, allowing surgeons to identify and remove cancerous tissues more accurately.

3. Glioma Surgery:

In neurosurgery, 5-ALA HCl is particularly useful for enhancing the resection of gliomas, which are brain tumors.

4. Actinic Keratosis Treatment:

Actinic keratosis is a precancerous skin condition caused by sun exposure. 5-ALA HCl is applied topically to the affected skin areas, where it is converted to PpIX. Exposure to light then triggers the production of ROS, leading to the destruction of the abnormal cells.

5. Bladder Cancer Diagnosis:

5-ALA HCl can be used to aid in the diagnosis of bladder cancer.

6. Agriculture and Photobiomodulation:

5-ALA HCl has important applications in agriculture and photobiomodulation. In plants, it can lead to the accumulation of chlorophyll, which might enhance photosynthesis and plant growth.

Aminolevulinic acid HCl Preparation Method

The preparation of 5-Aminolevulinic Acid Hydrochloride (5-ALA HCl) involves several steps. Usually, 5-ALA is synthesized first and then synthesized with hydrochloric acid.

Here’s a general outline of the synthesis process:

1. Starting Materials:

The primary starting materials for the synthesis of 5-ALA HCl are succinyl-CoA and glycine.

2. Biosynthesis of 5-ALA:

The biosynthesis of 5-ALA involves several enzymatic reactions in the heme biosynthesis pathway.

The key steps are as follows:

1. Condensation: Succinyl-CoA and glycine condense to form 5-aminolevulinic acid (5-ALA) in the presence of the enzyme 5-aminolevulinic acid synthase (ALAS).
2. Reaction: This reaction is carried out in the mitochondria of cells and is the first committed step in heme biosynthesis.

3. Conversion to 5-ALA Hydrochloride:

5-ALA reacts with hydrochloric acid (HCl) to form 5-aminolevulinic acid hydrochloride, which is more stable and readily soluble in water。

4. Purification and Isolation:

The resulting 5-ALA HCl solution is usually purified and isolated through processes such as filtration, crystallization, or precipitation.

5. Drying and Formulation:

The purified 5-ALA HCl is then typically dried to remove any remaining solvent or water. The final product is a white or off-white crystalline powder.

It’s important to note that the synthesis of 5-Aminolevulinic Acid Hydrochloride involves both enzymatic reactions and chemical steps. The enzymatic reactions are usually carried out using microbial cultures or plant extracts. If you need high-quality and purity aminolevulinic acid hydrochloride. Please contact us for the best quote. We provide free samples for testing and corresponding technical support.

5-ALA HCl Safety and Risk

5-Aminolevulinic acid hydrochloride (5-ALA HCl) is generally safe, but its potential hazards remain when used:

Security considerations:

1. Allergic reactions: Allergic reactions to 5-ALA HCl are rare, but should be avoided by individuals who are sensitive to this compound or its components.
2. Photosensitization: One of the main applications of 5-ALA HCl is photodynamic therapy (PDT), which is used to sensitize cells to light. After administration, patients may become more sensitive to light, especially sunlight, for a period of time. Skin reactions, including redness, burning, and blistering, may occur if the skin is exposed to the sun or certain types of artificial light.
3. SIDE EFFECTS: Some people may experience mild side effects after taking 5-ALA HCl, especially when used with photodynamic therapy.

Risk Mitigation:

1. Sun protection: Advise patients undergoing photodynamic therapy to avoid sun exposure and to use protective clothing, sunglasses, and sunscreen during periods of increased photosensitivity.
2. Dosage Control: Ensuring correct dosage and administration is critical to minimizing risks associated with 5-ALA HCl.

5-Aminolevulinic Acid Hydrochloride Research and Future Development

Research on 5-aminolevulinic acid hydrochloride (5-ALA HCl) is focused on the ongoing exploration of its potential applications, mechanism of action, and therapeutic uses.

Mainly include the following areas:

1. Advances in Photodynamic Therapy (PDT): Optimizing PDT protocols to enhance therapeutic efficacy while minimizing side effects.
2. Cancer Therapy: The use of 5-ALA HCl in cancer therapy is an active area of research.
3. Drug Delivery Systems: Researchers are exploring innovative drug delivery systems to enhance the targeted delivery of 5-ALA HCl to specific tissues or cells. This can improve treatment efficiency and reduce potential side effects.
4. Combination therapy: Researchers are studying the potential of combining 5-ALA HCl with other therapeutic drugs to enhance the effects of treatment. For example, combining 5-ALA HCl with immune checkpoint inhibitors in cancer therapy may have synergistic effects.
5. New formulations: Efforts to develop new formulations of 5-ALA HCl, such as topical creams or gels, could expand its range of applications and make treatment more accessible and convenient for patients.