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S2876 Sigma-Aldrich

Spermine tetrahydrochloride

powder or crystals

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

  • CAS Number 306-67-2

  • Empirical Formula (Hill Notation) C10H26N4 · 4HCl

  • Molecular Weight 348.18

  •  Beilstein/REAXYS Number 3911771

  •  EC Number 206-189-8

  •  MDL number MFCD00012914

  •  PubChem Substance ID 24278007

  •  NACRES NA.77

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Properties

Related Categories Amino Acid, Application Index, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents,
Quality Level   200
form   powder or crystals
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)

Description

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Preparation Note

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

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
EJ7230000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Exposure to harsh conditions, cellular damage, and other factors can cause stress on cells. Stress attributed directly and indirectly to oxygen is referred to as oxidative stress, which is imposed on...
Keywords: Antimicrobials, Bioactive small molecules, Cancer, Diseases, Neurodegenerative Diseases, Oxidations

Sensor Dyes

In 1998 R.F. Furchgott, L.J. Ignarro, and F. Murad received the Nobel Prize in Physiology and Medicine for their discoveries concerning nitric oxide as a signaling molecule in the cardiovascular syst...
Monika Baeumle
BioFiles 2011, 6.3, 23.
Keywords: Applications, Biochemistry, Biological processes, Cancer, Cardiovascular, Central Nervous System, Diseases, Extinction coefficient, Indicators, Inflammation, Methods, Microscopy, Neurotransmission, Sol-gel, Type

Peer-Reviewed Papers
15

References

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