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S2626

Sigma-Aldrich

Spermidine

≥99% (GC)

Synonym(s):

1,8-Diamino-4-azaoctane, N-(3-Aminopropyl)-1,4-diaminobutane

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About This Item

Linear Formula:
NH2(CH2)3NH(CH2)4NH2
CAS Number:
124-20-9
Molecular Weight:
145.25
Beilstein/REAXYS Number:
1698591
EC Number:
204-689-0
MDL number:
MFCD00008229
UNSPSC Code:
12352200
PubChem Substance ID:
24899529
NACRES:
NA.32

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)

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

Application

Spermidine has been used:
  • in the preparation of 5x transcription buffer
  • in the treatment of double-stranded RNA along with other reagents to increase the uptake of dsRNA by nematodes
  • 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.

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pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

233.6 °F - closed cup

flash_point_c

112 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Quantitative Detection of Double-Stranded RNA-Mediated Gene Silencing of Parasitism Genes in Heterodera glycines.
Sukno SA
Journal of Nematology, 39(2), 145-152 (2007)
In vitro Reconstitution Assay of miRNA Biogenesis by Arabidopsis DCL1.
Wang T
Bio-protocol, 5(8), e1454-e1454 (2015)
Evidence for the contribution of NOS1 gene polymorphism (rs3782206) to prefrontal function in schizophrenia patients and healthy controls.
Zhang Z
Neuropsychopharmacology, 40(6), 1383-1394 (2015)
Michi Miura et al.
Chromosome research : an international journal on the molecular, supramolecular and evolutionary aspects of chromosome biology, 28(3-4), 381-393 (2020-10-19)
CUT&RUN is a powerful tool to study protein-DNA interactions in vivo. DNA fragments cleaved by the targeted micrococcal nuclease identify the footprints of DNA-binding proteins on the chromatin. We performed CUT&RUN on human lung carcinoma cell line A549 maintained in
Varun K Gupta et al.
Nature neuroscience, 16(10), 1453-1460 (2013-09-03)
Age-dependent memory impairment is known to occur in several organisms, including Drosophila, mouse and human. However, the fundamental cellular mechanisms that underlie these impairments are still poorly understood, effectively hampering the development of pharmacological strategies to treat the condition. Polyamines
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