5-Aminolevulinic acid phosphate
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5-Aminolevulinic acid phosphate

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Category
Other Unnatural Amino Acids
Catalog number
BAT-015994
CAS number
868074-65-1
Molecular Formula
C5H12NO7P
Molecular Weight
229.12
IUPAC Name
5-amino-4-oxopentanoic acid;phosphoric acid
Synonyms
Aminolevulinic acid phosphate; Pentanoic acid, 5-amino-4-oxo-, phosphate (1:1); delta-Aminolevulinic acid phosphate; 5-ALA phosphate
Related CAS
106-60-5 (free base) 5451-09-2 (hydrochloride)
Appearance
Solid Powder
Purity
≥95%
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Solubility
Soluble in DMSO
InChI
InChI=1S/C5H9NO3.H3O4P/c6-3-4(7)1-2-5(8)9;1-5(2,3)4/h1-3,6H2,(H,8,9);(H3,1,2,3,4)
InChI Key
XWNWBYZHOAIHTK-UHFFFAOYSA-N
Canonical SMILES
C(CC(=O)O)C(=O)CN.OP(=O)(O)O
1. 5-Aminolevulinic acid and sodium ferrous citrate ameliorate muscle aging and extend healthspan in Drosophila
Naoko Nozawa, et al. FEBS Open Bio. 2022 Jan;12(1):295-305. doi: 10.1002/2211-5463.13338. Epub 2021 Dec 12.
Declines in mitochondrial functions are associated with aging. The combination of 5-aminolevulinic acid (5-ALA) and sodium ferrous citrate (SFC) improves mitochondrial functions in cultured cells. In this study, we investigated the effects of dietary supplementation with 5-ALA and SFC (5-ALA/SFC) on the healthspan and life span of Drosophila melanogaster. Adult Drosophila fruit flies were fed cornmeal food containing various concentrations of 5-ALA/SFC. Locomotor functions, life span, muscle architecture, and age-associated changes in mitochondrial function were analyzed. We found that feeding 5-ALA/SFC mitigated age-associated declines in locomotor functions and extended organismal life span. Moreover, 5-ALA/SFC preserved muscle architecture and maintained the mitochondrial membrane potential in aged animals. Since 5-ALA phosphate/SFC is used as a human dietary supplement, our results suggest that it could be used to slow the age-related declines in muscle functions, prevent age-associated clinical conditions such as frailty, and extend healthspan and life span.
2. Antiviral Effects of 5-Aminolevulinic Acid Phosphate against Classical Swine Fever Virus: In Vitro and In Vivo Evaluation
Shizuka Hirose, Norikazu Isoda, Loc Tan Huynh, Taksoo Kim, Keiichiro Yoshimoto, Tohru Tanaka, Kenjiro Inui, Takahiro Hiono, Yoshihiro Sakoda Pathogens. 2022 Jan 27;11(2):164. doi: 10.3390/pathogens11020164.
The inhibitory effects of 5-aminolevulinic acid phosphate (5-ALA), an important amino acid for energy production in the host, against viral infections were previously reported. Here, the antiviral effects of 5-ALA against classical swine fever virus (CSFV) belonging to the genus Pestivirus in the Flaviviridae family and its possible mechanisms were investigated. CSFV replication was suppressed in swine cells supplemented with 5-ALA or its metabolite, protoporphyrin IX (PPIX). The infectivity titer of CSFV was decreased after mixing with PPIX extracellularly. In addition, the activities of the replication cycle were decreased in the presence of PPIX based on the CSFV replicon assay. These results showed that PPIX exerted antiviral effects by inactivating virus particles and inhibiting the replication cycle. To evaluate the in vivo efficacy of 5-ALA, pigs were supplemented daily with 5-ALA for 1 week before virus inoculation and then inoculated with a virulent CSFV strain at the 107.0 50% tissue culture infectious dose. The clinical scores of the supplemented group were significantly lower than those of the nonsupplemented group, whereas the virus growth was not. Taken together, 5-ALA showed antiviral effects against CSFV in vitro, and PPIX played a key role by inactivating virus particles extracellularly and inhibiting the replication cycle intracellularly.
3. 5-Aminolevulinic acid improves chicken sperm motility
Shin Taniguchi, Zhendong Zhu, Mei Matsuzaki, Masaoki Tsudzuki, Teruo Maeda Anim Biosci. 2021 Dec;34(12):1912-1920. doi: 10.5713/ab.21.0021. Epub 2021 Apr 23.
Objective: This study investigated the effects of 5-aminolevulinic acid (5-ALA) on the motility parameters, mitochondrial membrane depolarization, and ATP levels in chicken sperm. Methods: The pooled semen from Barred Plymouth Rock males was used. In the first experiment, the semen was diluted 4-times with phosphate-buffered saline (PBS (-)) containing various concentrations (0, 0.01, 0.05, and 0.1 mM) of 5-ALA, and then the sperm motility parameters after incubation were evaluated by computer-assisted sperm analysis (CASA). In the second experiment, the semen was diluted 4-times with PBS (-) containing 0.05 mM 5-ALA, and then sperm mitochondrial membrane depolarization and ATP levels after 1.5 h of incubation were analyzed with the MitoPT® JC-1 Assay and ATP Assay kits, respectively. In the third experiment, the semen was removed from the seminal plasma and resuspended with the mediums of PBS (-), PBS (-) supplemented with CaCl2 and MgCl2 (PBS (+)) + 5-ALA, PBS (+) + caffeine, and PBS (+) + caffeine + 5-ALA. Then, the sperm motility parameters after incubation were evaluated by CASA. In the last experiment, the semen was treated with the mediums of PBS (-), PBS (-) + 5-ALA, 5.7% glucose, 5.7% glucose + 5-ALA after removing the seminal plasma, and then the sperm motility parameters were evaluated by CASA. Results: The addition of 0.05 mM 5-ALA significantly increased the chicken sperm motility, progressive motility, linearity, average path velocity, curvilinear velocity, straight-line velocity, and the wobble. The sperm mitochondrial membrane depolarization was also increased by the 5-ALA treatment. The 5-ALA treatment decreased the sperm ATP levels. Both the caffeine treatment and glucose treatment decreased the sperm motility during incubation period. Conclusion: 5-ALA might increase sperm mitochondrial membrane depolarization to utilize the ATP for enhancing sperm movement.
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