Spermidine
From Wikipedia, the free encyclopedia
| Spermidine | |
|---|---|
 |
|
 |
|
|
N-(3-Aminopropyl)butane-1,4-diamine[citation needed] |
|
|
Other names
1,5,10-Triazadecane[citation needed] |
|
| Identifiers | |
| CAS number | 124-20-9  |
| PubChem | 1102 |
| ChemSpider | 1071  |
| EC number | 204-689-0 |
| UN number | 2735 |
| DrugBank | DB03566 |
| KEGG | C00315 |
| MeSH | Spermidine |
| ChEBI | CHEBI:16610 |
| ChEMBL | CHEMBL19612 |
| IUPHAR ligand | 2390 |
| RTECS number | EJ7000000 |
| Beilstein Reference | 1698591 |
| Gmelin Reference | 454510 |
| 3DMet | B01214 |
| Jmol-3D images | Image 1 |
|
|
|
|
| Properties | |
| Molecular formula | C7H19N3 |
| Molar mass | 145.25 g mol−1 |
| Exact mass | 145.157897623 g mol−1 |
| Appearance | Colourless, transparent liquid |
| Density | 925 mg mL−1 |
| Melting point |
22-25 °C, 295-298 K, 72-77 °F |
| Solubility in water | 145 g L−1 (at 20 °C) |
| log P | −0.504 |
| Refractive index (nD) | 1.479 |
| Hazards | |
| GHS pictograms |  |
| GHS signal word | DANGER |
| GHS hazard statements | H314 |
| GHS precautionary statements | P280, P305+351+338, P310 |
| EU classification |  C |
| R-phrases | R34 |
| S-phrases | S26, S36/37/39 |
| Flash point | 112 °C |
| Related compounds | |
| Related compounds | Norspermidine |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
|
| Infobox references |
Spermidine is a polyamine involved in cellular metabolism. Its known actions include:
- Inhibition of neuronal nitric oxide synthase, nNOS[1]
- Assisting the in vitro process of transcribing RNA via stimulation of T4 polynucleotide kinase and T7 RNA polymerase activity; it binds to and precipitates DNA and is utilized in purifying DNA-binding proteins[2]
- Regulation and promotion of plant growth - as a polyamine plant growth regulator it is also a plant hormone-promoting somatic embryogenesis.[3][4][5][6][7][8][9]
Spermidine has also been found to reduce the amount of aging in yeast, flies, worms, and human immune cells by inducing autophagy.[10]
Contents |
[edit] Sources
[edit] Biochemical actions
- Inhibits neuronal nitric oxide synthase (nNOS)
- Binds and precipitates DNA
- May be used for purification of DNA-binding proteins
- Stimulates T4 polynucleotide kinase and T7 RNA polymerase activity
- Polyamine plant growth regulator
[edit] Some of the uses
- Spermidine can be used in electroporation while transferring the DNA into the cell under the electrical impulse.
- Stimulating autophagy. Recently Tirupathi Pichiah et.al., suggested that spermidine may be helpful for treating type 2 diabetes[13] .
[edit] See also
[edit] References
- ^ Hu, J; Mahmoud, MI; El-Fakahany, EE (1994). "Polyamines inhibit nitric oxide synthase in rat cerebellum". Neuroscience letters 175 (1–2): 41–5. doi:10.1016/0304-3940(94)91073-1. PMID 7526294.
- ^ Wan, CY; Wilkins, TA (1993). "Spermidine facilitates PCR amplification of target DNA". PCR methods and applications 3 (3): 208–10. PMID 8118404.
- ^ Cull, M; McHenry, CS (1990). "Preparation of extracts from prokaryotes". Methods in enzymology. Methods in Enzymology 182: 147–53. doi:10.1016/0076-6879(90)82014-S. ISBN 9780121820831. PMID 2107372.
- ^ Blethen, SL; Boeker, EA; Snell, EE (1968). "Argenine decarboxylase from Escherichia coli. I. Purification and specificity for substrates and coenzyme". The Journal of biological chemistry 243 (8): 1671–7. PMID 4870599.
- ^ Wu, WH; Morris, DR (1973). "Biosynthetic arginine decarboxylase from Escherichia coli. Subunit interactions and the role of magnesium ion". The Journal of biological chemistry 248 (5): 1696–9. PMID 4571774.
- ^ Tabor, CW; Tabor, H (1984). "Polyamines". Annual review of biochemistry 53: 749–90. doi:10.1146/annurev.bi.53.070184.003533. PMID 6206782.
- ^ Krug, MS; Berger, SL (1987). "First-strand cDNA synthesis primed with oligo(dT)". Methods in enzymology. Methods in Enzymology 152: 316–25. doi:10.1016/0076-6879(87)52036-5. ISBN 9780121820534. PMID 2443800.
- ^ Karkas, JD; Margulies, L; Chargaff, E (1975). "A DNA polymerase from embryos of Drosophila melanogaster. Purification and properties". The Journal of biological chemistry 250 (22): 8657–63. PMID 241752.
- ^ Bouché, JP (1981). "The effect of spermidine on endonuclease inhibition by agarose contaminants". Analytical biochemistry 115 (1): 42–5. doi:10.1016/0003-2697(81)90519-4. PMID 6272602.
- ^ Tobias Eisenberg, Heide Knauer, Alexandra Schauer, Sabrina Büttner, Christoph Ruckenstuhl, Didac Carmona-Gutierrez, Julia Ring, Sabrina Schroeder, Christoph Magnes, Lucia Antonacci, Heike Fussi, Luiza Deszcz, Regina Hart, Elisabeth Schraml, Alfredo Criollo, Evgenia Megalou, Daniela Weiskopf, Peter Laun, Gino Heeren, Michael Breitenbach, Beatrix Grubeck-Loebenstein, Eva Herker, Birthe Fahrenkrog, Kai-Uwe Fröhlich, Frank Sinner, Nektarios Tavernarakis, Nadege Minois, Guido Kroemer, Frank Madeo (4 October 2009). "Induction of autophagy by spermidine promotes longevity,". Nature Cell Biology 11 (11): 1305–14. doi:10.1038/ncb1975. PMID 19801973. http://www.nature.com/ncb/journal/v11/n11/abs/ncb1975.html.
- ^ Leeuwenhoek, A. van (1678) Observationes D. Anthonii Leeuwenhoek, de natis e semine genitali animalculis. Letter dated November 1677. Philos. Trans. Roy. Soc. London, 12, 1040-1043.
- ^ Eisenberg, Tobias; Knauer, Heide; Schauer, Alexandra; Büttner, Sabrina; Ruckenstuhl, Christoph; Carmona-Gutierrez, Didac; Ring, Julia; Schroeder, Sabrina et al (2009). "Induction of autophagy by spermidine promotes longevity". Nature Cell Biology 11 (11): 1305–14. doi:10.1038/ncb1975. PMID 19801973.
- ^ Tirupathi Pichiah, PB; Suriyakalaa, U, Kamalakkannan, S, Kokilavani, P, Kalaiselvi, S, SankarGanesh, D, Gowri, J, Archunan, G, Cha, YS, Achiraman, S (2011 Oct). "Spermidine may decrease ER stress in pancreatic beta cells and may reduce apoptosis via activating AMPK dependent autophagy pathway". Medical hypotheses 77 (4): 677–9. doi:10.1016/j.mehy.2011.07.014. PMID 21831529.
