S4264

Sigma-Aldrich

Spermine

BioReagent, suitable for cell culture

Synonym(s):
N,N′-Bis(3-aminopropyl)-1,4-diaminobutane, Neuridine, Gerontine, Musculamine
Linear Formula:
NH2(CH2)3NH(CH2)4NH(CH2)3NH2
CAS Number:
Molecular Weight:
202.34
Beilstein/REAXYS Number:
1750791
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.75
Pricing and availability is not currently available.

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

HN(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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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

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).
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).

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

C

Risk Statement

34

Safety Statement

26-36/37/39-45

RIDADR

UN 3259PSN2 8 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Fractionation of chromosome 15 with an affinity-based approach using magnetic beads
Vitharana S N and Wilson G S
Genomics, 87(1), 158-164 (2006)
Dong M, et al.
Journal of Immunology, 178(5), 3016-3022 (2007)
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...
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...
Navasona Krishnan et al.
Nature chemical biology, 10(7), 558-566 (2014-05-23)
PTP1B, a validated therapeutic target for diabetes and obesity, has a critical positive role in HER2 signaling in breast tumorigenesis. Efforts to develop therapeutic inhibitors of PTP1B have been frustrated by the chemical properties of the active site. We define...

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