Aminolevulinic acid

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δ-Aminolevulinic acid
Aminolevulinic acid.svg
Systematic (IUPAC) name
5-amino-4-oxo-pentanoic acid
Clinical data
Pregnancy cat.
  • C
Legal status
  • Rx only
Identifiers
CAS number 106-60-5 YesY
ATC code L01XD04
PubChem CID 137
DrugBank DB00855
ChemSpider 134 YesY
UNII 88755TAZ87 YesY
KEGG D07567 YesY
ChEBI CHEBI:356416 YesY
ChEMBL CHEMBL601 YesY
Chemical data
Formula C5H9NO3 
Mol. mass 131.13 g/mol
 YesY (what is this?)  (verify)

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 which the speed of synthesis of 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.

Biosynthesis[edit]

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 2,1-aminomutase. This pathway is known as the C5 or Beale pathway.[1][2]

Clinical significance[edit]

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.[3] 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.[4][5]

Being a precursor of photosensitizer, aminolevulinic acid is also a used as an agent for photodynamic therapy.

Cancer diagnosis[edit]

Photodynamic detection is the use of photosensitive drugs with a light source of the right wavelength for the detection of cancer, using fluorescence of the drug.[citation needed]

5-Aminolevulinic acid can be used to visualize bladder cancer.[6]

Cancer treatment[edit]

Photodynamic therapy (PDT) treatment possibilities include those for cancer of the prostate, breast, giant BCC (skin), cervix, recurrent bladder, vulvar, brain (human glioblastoma cells), HPV, lung, stomach, head and neck, penis, and colon, as well as those for leukemia, Barrett's esophagus, squamous cell carcinoma (SCC), Bowen's disease, and other types of cancer.

See also[edit]

References[edit]

  1. ^ Beale SI (August 1990). "Biosynthesis of the Tetrapyrrole Pigment Precursor, delta-Aminolevulinic Acid, from Glutamate". Plant Physiol. 93 (4): 1273–9. doi:10.1104/pp.93.4.1273. PMC 1062668. PMID 16667613. 
  2. ^ Willows, R.D. (2004). "Chlorophylls". In Goodman, Robert M. Encyclopaedia of Plant and Crop Science. Marcel Dekker. pp. 258–262. ISBN 0-8247-4268-0. 
  3. ^ Eyüpoglu, Ilker Y.; Buchfelder, Michael; Savaskan, Nic E. (2013). "Surgical resection of malignant gliomas—role in optimizing patient outcome". Nature Reviews Neurology 9 (3): 141–51. doi:10.1038/nrneurol.2012.279. PMID 23358480. 
  4. ^ 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:10.1016/S1470-2045(06)70665-9. PMID 16648043. 
  5. ^ Eyüpoglu, Ilker Y.; Hore, Nirjhar; Savaskan, Nic E.; Grummich, Peter; Roessler, Karl; Buchfelder, Michael; Ganslandt, Oliver (2012). Berger, Mitch, ed. "Improving the Extent of Malignant Glioma Resection by Dual Intraoperative Visualization Approach". PLoS ONE 7 (9): e44885. doi:10.1371/journal.pone.0044885. PMC 3458892. PMID 23049761. 
  6. ^ "Bacillus Calmette-Guérin Immunotherapy for Bladder Cancer Overview of BCG Immunotherapy".