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S3256

Sigma-Aldrich

Spermine

≥97%

Synonym(s):

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

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About This Item

Linear Formula:
NH2(CH2)3NH(CH2)4NH(CH2)3NH2
CAS Number:
71-44-3
Molecular Weight:
202.34
Beilstein:
1750791
EC Number:
200-754-2
MDL number:
MFCD00008215
UNSPSC Code:
12352116
PubChem Substance ID:
24899550
NACRES:
NA.25

biological source

microbial
synthetic

description

form: solid or semisolid

Assay

≥97%

bp

150 °C/5 mmHg (lit.)

mp

28-30 (lit.)

solubility

water: 50 mg/mL, clear, colorless

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)

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General description

Spermine is a polyamine, which functions as a free radical scavenger. It modulates gene expression, chromatin stabilization and prevents DNA damage. Spermine inhibits endonuclease-mediated DNA fragmentation.

Application

Spermine has been used:
  • as an inositol 1,4,5-trisphosphate receptor (IP3R)/glucose-regulated protein 75 (Grp75)/voltage-dependent anion channel 1 (VDAC1)/mitochondrial calcium uniporter (MCU) agonist to activate MCU in mouse podocytes
  • in the biolistic transfection of filarial parasites
  • for the production of adeno-associated virus (AAV)

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).

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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IP 3 R-Grp75-VDAC1-MCU calcium regulation axis antagonists protect podocytes from apoptosis and decrease proteinuria in an Adriamycin nephropathy rat model
Xu H, et al.
BMC Nephrology, 19(1), 140-140 (2018)
Brugia malayi: transient transfection by microinjection and particle bombardment
Higazi TB, et al.
Experimental Parasitology, 100(2), 95-102 (2002)
Using mammalian GFP reconstitution across synaptic partners (mGRASP) to map synaptic connectivity in the mouse brain.
Feng L, et al.
Nature Protocols, 9(10), 2425-2425 (2014)
H C Ha et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(19), 11140-11145 (1998-09-16)
The polyamines are small organic cations that are absolutely required for eukaryotic cell growth. Although their growth requirements are well established, the molecular functions of the polyamines are ill-defined. Oxidative damage to DNA by reactive oxygen species is a continual
Lydia P P Liew et al.
Bioorganic & medicinal chemistry letters, 23(2), 452-454 (2012-12-26)
Screening of synthesized and isolated marine natural products for in vitro activity against four parasitic protozoa has identified the ascidian metabolite 1,14-sperminedihomovanillamide (orthidine F, 1) as being a non-toxic, moderate growth inhibitor of Plasmodium falciparum (IC(50) 0.89 μM). Preliminary structure-activity
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