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Merck

S3256

Spermine

≥97%

Sinónimos:

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

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About This Item

Fórmula lineal:
NH2(CH2)3NH(CH2)4NH(CH2)3NH2
Número CAS:
71-44-3
Peso molecular:
202.34
UNSPSC Code:
12352116
NACRES:
NA.25
PubChem Substance ID:
24899550
EC Number:
200-754-2
Beilstein/REAXYS Number:
1750791
MDL number:
MFCD00008215

Nombre del producto

Spermine, ≥97%

InChI key

PFNFFQXMRSDOHW-UHFFFAOYSA-N

InChI

1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2

SMILES string

[H]N(CCCN)CCCCN([H])CCCN

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

Quality Level

200

Gene Information

human ... GRIN2B(2904)
rat ... Grin2a(24409)

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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 agonist/antagonist at the polyamine site. Plays a role in cellular proliferation and differentiation; inhibits neuronal nitric oxide synthase (nNOS).
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).

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.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Clase de almacenamiento

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
BCCN7109
BCCN4101
BCCN0639
BCCL3738
BCCM1182

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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
H Hosseinkhani et al.
Gene therapy, 11(2), 194-203 (2004-01-09)
Dextran-spermine cationic polysaccharide was prepared by means of reductive amination between oxidized dextran and the natural oligoamine spermine. The formed Schiff-base imine-based conjugate was reduced with borohydride to obtain the stable amine-based conjugate. The transfection efficiency of the synthetic dextran-spermine
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