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δ-Aminolevulinic acid
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| Systematic (IUPAC) name | |
| 5-amino-4-oxo-pentanoic acid | |
| Identifiers | |
| CAS number | 106-60-5 |
| ATC code | L01XD04 |
| PubChem | 137 |
| DrugBank | APRD00793 |
| Chemical data | |
| Formula | C5H9NO3 |
| Mol. mass | 131.13 g/mol |
| SMILES | eMolecules & PubChem |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status | |
| Routes | ? |
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δ-Aminolevulinic acid (dALA or δ-ALA or 5ala or 5-aminolevulinic acid ) is the first compound in the porphyrin synthesis pathway, the pathway that leads to heme in mammals and chlorophyll in plants.
In plants, production of δ-ALA is the step on that the speed of synthesis chlorophyll is regulated. Plants that are fed by external δ-ALA accumulate toxic amounts of chlorophyll precursor, protochlorophyllide, indicating that the synthesis of this intermediate is not suppressed anywhere downwards in the chain of reaction. Protochlorophyllide is a strong photosensitizer in plants.
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Production
In non-photosynthetic eukaryotes such as animals, insects, fungi, and protozoa, as well as the α-proteobacteria group of bacteria, it is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway.
In plants, algae, bacteria (except for the α-proteobacteria group) and archaea, it is produced from glutamic acid via glutamyl-tRNA and glutamate-1-semialdehyde. The enzymes involved in this pathway are glutamyl-tRNA synthetase, glutamyl-tRNA reductase, and glutamate-1-semialdehyde aminotransferase. This pathway is known as the C5 or Beale pathway.[1][2]
Clinical significance
It elicits synthesis and accumulation of fluorescent porphyrins (protoporphyrin IX) in epithelia and neoplastic tissues, among them malignant gliomas. It is used to visualise tumorous tissue in neurosurgical procedures. Studies have shown that the intraoperative use of this guiding method may reduce the tumour residual volume and prolong progression-free survival in patients suffering from this disease.[3]
dALA or 5ala is also a photosensitizer for photodynamic therapy.
Cancer Treatment
Photodynamic therapy is a non conventional light therapy for treatment of cancer. Photodynamic Therapy also known as PDT, uses photosensitive drugs (5-ALA, Foscan, Metvix, Tookad, WST09, WST11, Photofrin and Visudyne) which are trigged by light from a specific wavelength usually red or infrared on the light spectrum chart. The drugs are administered in different ways depending on the type of cancer being treated. When the light is applied to the drug it causes a singlet oxygen molecule to form which attacks the tumor and destroys it from the inside out. Photodynamic Therapy is a proven alternative treatment for many cancers. Clinical trials have taken place world wide and several hospitals do offer PDT as a primary cancer treatment. Website devoted to Photodynamic therapy - 5ala.net
Photodynamic Detection is the use of photosensitive drugs with a light source of the right wavelength for the detection of cancer using fluoresence of the drug. PDT treatment possibilities - Prostate, Breast, Giant BCC (Skin), Cervix, recurrent Bladder, Vulvar, Brain (human glioblastoma cells), HPV , Colon, Leukemia, Barretts Oesophagus, Lung, Stomach, Head and Neck, squamous cell carcinoma (SCC) , Bowen's disease, Penile, and other types of cancer
References
- ^ Beale, Samuel I. (1990) Biosynthesis of the tetrapyrrole pigment precursor, d-aminolevulinic acid, from glutamate. Plant Physiology, 93(4), 1273-1279
- ^ Willows R.D. (2004) Chlorophylls In: Encylopaedia of Plant and Crop Science. pp 258-262, Ed: Robert M. Goodman. Marcel Dekker Inc, ISBN 0-8247-4268-0
- ^ Stummer W, Pichlmeier U, Meinel T, Wiestler OD, Zanella F, Reulen HJ (2006). "Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial". Lancet Oncol. 7 (5): 392–401. doi:. PMID 16648043.
See also
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