S2626

Spermidine

≥99% (GC)

• Synonym(s): 1,8-Diamino-4-azaoctane, N-(3-Aminopropyl)-1,4-diaminobutane
• Linear Formula: NH₂(CH₂)₃NH(CH₂)₄NH₂
• CAS Number: 124-20-9
• Molecular Weight: 145.25
• Beilstein: 1698591
• EC Number: 204-689-0
• MDL number: MFCD00008229
• UNSPSC Code: 12352200
• PubChem Substance ID: 24899529
• NACRES: NA.32

Properties

• biological source: synthetic
• Quality Level: 200
• Assay: ≥99% (GC)
• form: solid or liquid (clear)
• impurities: DNase, none detected; RNase, none detected; protease, none detected
• refractive index: n20/D 1.479 (lit.)
• mp: 22-25 °C
• solubility: water: 50 mg/mL, clear to very slightly hazy, colorless to very faintly yellow
• density: 0.925 g/mL at 25 °C (lit.)
• storage temp.: room temp
• SMILES string: NCCCCNCCCN
• InChI: 1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2
• InChI key: ATHGHQPFGPMSJY-UHFFFAOYSA-N
• Gene Information: rat ... Ppm1a(24666)

Description

General description

Spermidine, a natural biomolecule, is known for its wide-ranging health benefits, including anti-inflammatory effects, antioxidant properties, and improvements in respiratory function. It carries a positive charge at physiological pH, allowing it to interact with oppositely charged DNA and RNA. Dietary intake of spermidine is associated with a reduced risk of neurodegeneration, metabolic diseases, heart ailments, and cancer. Spermidine-induced autophagy has been shown to slow the rate of cognitive decline by clearing amyloid-beta plaques in the brain. Spermidine supplementation improves mitochondrial metabolism and translational activity. Moreover, spermidine exhibits cell-autonomous effects on cancer cells and influences their communication with immune effectors, leading to the acceleration of tumor-associated antigen identification and cancer cell death. Spermidine-mediated autophagy inhibits the activation of apoptosis in cancer cells and is linked to tissue development and cell differentiation. This natural compound is additionally recognized for its neuroprotective, and anti-aging properties and is naturally found in semen, as well as in various plant sources.[1]

The enzyme nitric oxide synthase (nNOS) is involved in the production of nitric oxide.[2]

Application

Spermidine has been used:

• in the preparation of 5x transcription buffer[3]
• in the treatment of double-stranded RNA along with other reagents to increase the uptake of dsRNA by nematodes[4]
• as a standard in the analytical study of rat brain polyamines (185)

Biochem/physiol Actions

Inhibits neuronal nitric oxide synthase (nNOS). Binds and precipitates DNA; may be used for purification of DNA binding proteins. Stimulates T₄ polynucleotide kinase activity.

Caution

Solutions should be sterile-filtered, not autoclaved, if sterile solution is necessary. Spermidine deaminates with time; solutions should be stored frozen. Prepare new solutions frequently.

Other Notes

Store under inert gas. Air sensitive; strongly hygroscopic.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363 - P405
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 3
• Flash Point(F): 233.6 °F - closed cup
• Flash Point(C): 112 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves