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Spermidine

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Spermidine
Skeletal formula of spermidine
Ball and stick model of spermidine
Names
IUPAC name
N-(3-Aminopropyl)butane-1,4-diamine[citation needed]
Other names
1,5,10-Triazadecane[citation needed]
Identifiers
3D model (JSmol)
3DMet
1698591
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.264 Edit this at Wikidata
EC Number
  • 204-689-0
454510
KEGG
MeSH Spermidine
RTECS number
  • EJ7000000
UN number 2735
  • InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2 ☒N
    Key: ATHGHQPFGPMSJY-UHFFFAOYSA-N ☒N
  • NCCCCNCCCN
Properties
C7H19N3
Molar mass 145.250 g·mol−1
Appearance Colourless, transparent liquid
Density 925 mg mL−1
145 g L−1 (at 20 °C)
log P −0.504
1.479
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
P280, P305+P351+P338, P310
Flash point 112 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Spermidine is a polyamine involved in cellular metabolism. Its known actions include:

  1. Inhibition of neuronal nitric oxide synthase, nNOS[1]
  2. 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]
  3. 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.Cite error: The <ref> tag has too many names (see the help page).

Sources

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

Some of the uses

  • Spermidine can be used in electroporation while transferring the DNA into the cell under the electrical impulse.
  • spermidine is listed at Us Patent application 10/566,411 as causing better skin elasticity as well as hydration at .25 to .5mg/kg orally
  • although the "odds ratio" is only 9 chances per 10 spermidine is published as giving mice about double longevity (KLM512 study at plos one) It is thought to be the active chemical at a treatment that has better odds ratio than 999 per 1000 at giving mice greater longevity)
  • Stimulating autophagy. Recently Tirupathi Pichiah et.al., suggested that spermidine may be helpful for treating type 2 diabetes[12] .

See also

References

  1. ^ 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.
  2. ^ Wan, CY; Wilkins, TA (1993). "Spermidine facilitates PCR amplification of target DNA". PCR methods and applications. 3 (3): 208–10. PMID 8118404.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ Tabor, CW; Tabor, H (1984). "Polyamines". Annual review of biochemistry. 53: 749–90. doi:10.1146/annurev.bi.53.070184.003533. PMID 6206782.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ Eisenberg, Tobias; Knauer, Heide; Schauer, Alexandra; Büttner, Sabrina; Ruckenstuhl, Christoph; Carmona-Gutierrez, Didac; Ring, Julia; Schroeder, Sabrina; Magnes, Christoph (2009). "Induction of autophagy by spermidine promotes longevity". Nature Cell Biology. 11 (11): 1305–14. doi:10.1038/ncb1975. PMID 19801973.
  12. ^ Tirupathi Pichiah, PB (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. {{cite journal}}: Check date values in: |date= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
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