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S2876

Sigma-Aldrich

Spermine tetrahydrochloride

powder or crystals, NMDA agonist/antagonist

Synonym(s):

N,N′-Bis(3-aminopropyl)-1,4-butanediamine tetrahydrochloride

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About This Item

Empirical Formula (Hill Notation):
C10H26N4 · 4HCl
CAS Number:
306-67-2
Molecular Weight:
348.18
Beilstein:
3911771
EC Number:
206-189-8
MDL number:
MFCD00012914
UNSPSC Code:
12352200
PubChem Substance ID:
24278007
NACRES:
NA.77

Product Name

Spermine tetrahydrochloride, powder or crystals

form

powder or crystals

Quality Level

200

mp

310-311 °C (dec.) (lit.)

solubility

water, high purity: 100 mg/ml

storage temp.

room temp

SMILES string

Cl.Cl.Cl.Cl.NCCCNCCCCNCCCN

InChI

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

InChI key

XLDKUDAXZWHPFH-UHFFFAOYSA-N

Gene Information

human ... GRIN1(2902)

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Application

Spermine tetrahydrochloride was used to precipitate DNA for flow cytometric analysis from fresh frozen breast cancer tissue, archival tissue of salivary gland, renal and thyroid tumors and red blood cells of chicken.
Used to precipitate DNA from low salt aqueous buffers.

Biochem/physiol Actions

Mixed NMDA 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 agonist/antagonist at the polyamine site. Plays a role in cellular proliferation and differentiation; inhibits neuronal nitric oxide synthase (nNOS).
Spermine, a polyamine, is derived from spermidine and is required for cell growth in eukaryotes. It acts as regulator of gene expression, inhibits DNA damage and protects the cells from damage by acting as free radical scavenger. In proteomics studies, spermine mediates rapid crystallization of DNA-binding proteins.

Preparation Note

Spermine tetrahydrochloride yields clear, colorless to light yellow solution in water at 100 mg/ml.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH9611
BCCH9612
BCCH1975
BCCH2312
BCCH1976

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E Bergers et al.
Journal of clinical pathology, 49(11), 931-937 (1996-11-01)
Conflicting results have been reported concerning the prognostic value of DNA flow cytometric variables (DNA ploidy, DNA index, %S phase fraction) in breast cancer. Selection bias and differences in treatment may have contributed to these conflicting prognostic results. Differences in
A S Jackson et al.
The British journal of nutrition, 40(3), 497-504 (1978-11-01)
1. Skinfold thickness, body circumferences and body density were measured in samples of 308 and ninety-five adult men ranging in age from 18 to 61 years. 2. Using the sample of 308 men, multiple regression equations were calculated to estimate
J Griffith et al.
Biochemistry, 24(1), 158-162 (1985-01-01)
The RecA protein of Escherichia coli, whether pure or in a crude cell lysate, will rapidly form small crystals (microcrystals) in the presence of low concentrations of spermidine. We describe the conditions of time, pH, and polyamine concentration over which
L L Vindeløv et al.
Cytometry, 3(5), 323-327 (1983-03-01)
A new modification of our detergent technique for the preparation of nuclei for flow cytometric DNA analysis is described. The attainment of low coefficients of variation of the peaks and of quantitative staining of nuclei from different tissues was a
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
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