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S2626

Spermidine

synthetic, ≥99% (GC), neuronal nitric oxide synthase (nNOS) inhibitor, solid or liquid (clear)

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
NACRES:
NA.32
PubChem Substance ID:
24899529
UNSPSC Code:
12352200
EC Number:
204-689-0
MDL number:
MFCD00008229
Beilstein/REAXYS Number:
1698591
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Product Name

Spermidine, ≥99% (GC)

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)

General description

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

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

Other Notes

Store under inert gas. Air sensitive; strongly hygroscopic.

Disclaimer

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.

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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

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP0835
BCCN1353
BCCL8426
BCCJ7187
BCCH2800

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Spermidine as a promising anticancer agent: Recent advances and newer insights on its molecular mechanisms
Parteek P, et al.
Frontiers in Chemistry, 11, 1164477-1164477 (2023)
In vitro Reconstitution Assay of miRNA Biogenesis by Arabidopsis DCL1.
Wang T
Bio-protocol, 5(8), e1454-e1454 (2015)
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)
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