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S4264 Sigma-Aldrich

Spermine

suitable for cell culture, BioReagent

Synonym: N,N′-Bis(3-aminopropyl)-1,4-diaminobutane, Gerontine, Musculamine, Neuridine

  • CAS Number 71-44-3

  • Linear Formula NH2(CH2)3NH(CH2)4NH(CH2)3NH2

  • Molecular Weight 202.34

  •  Beilstein/REAXYS Number 1750791

  •  EC Number 200-754-2

  •  MDL number MFCD00008215

  •  PubChem Substance ID 24899594

  •  NACRES NA.75

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Properties

Related Categories Application Index, Biochemicals and Reagents, Cell Biology, Cell Culture, Cell Signaling Enzymes,
Quality Level   200
biological source   microbial
  synthetic
product line   BioReagent
assay   ≥96%
form   solid
application(s)   cell culture | mammalian: suitable
bp   150 °C/5 mmHg (lit.)
mp   28-30 (lit.)
solubility   H2O: 50 mg/mL
storage temp.   2-8°C
SMILES string   [H]N(CCCN)CCCCN([H])CCCN
InChI   1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
InChI key   PFNFFQXMRSDOHW-UHFFFAOYSA-N
Gene Information   human ... GRIN2B(2904)
rat ... Grin2a(24409)

Description

Application

Spermine has been used:
• in the buffer, to swap the divalent cations in the MgSO4 protocol to stabilize the integrity of the chromosomes
• in the preparation of modified mica surfaces from freshly cleaved mica surfaces
• to study its effects on survival in mice with sepsis and to estimate the role of spermine in lethal systemic inflammatory diseases

Biochem/physiol Actions

Mixed NMDA glutamate receptor agonist/antagonist at the polyamine site. Neuroprotective effects have been observed at high concentrations (1 mM), while neurotoxicity is observed at lower concentrations. It enhances agonist effectiveness at the strychnine-insensitive glycine site. Plays a role in cellular proliferation and differentiation; inhibits neuronal nitric oxide synthase (nNOS).

Spermine together with putrescine and spermidine compose a family of polyamines (polycations) that are required for the growth and survival of the vast majority of living cells. Polyamines interact with negatively charged molecules such as proteoglycans, glycated proteins and nucleic acids (DNA and RNA). Biogenic polyamines are found to modulate protein synthesis at different levels. This effect may be explained by the ability of polyamines to bind and influence the secondary structure of tRNA, mRNA, and rRNA. Spermine also helps stabilize nucleic acid helical structure and the conformation of glycated proteins such as the histones. Spermine and spermidine are components of various nucleic acid transfection protocols.

Mixed NMDA glutamate receptor agonist/antagonist at the polyamine site. Neuroprotective effects have been observed at high concentrations (1 mM), while neurotoxicity is observed at lower concentrations. It enhances agonist effectiveness at the strychnine-insensitive glycine site. Plays a role in cellular proliferation and differentiation; inhibits neuronal nitric oxide synthase (nNOS).

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3259PSN2 8 / PGII
WGK Germany 
WGK 3
RTECS 
EJ7175000
Flash Point(F) 
230.0 °F - closed cup
Flash Point(C) 
110 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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