Spermine (formerly known as NSC 268508), a potent polycationic biogenic polyamine derived from spermidine, functions directly as a free radical scavenger to protect DNA from free radical attack. Spermine can be used in a wide variety of biological applications as a supplement or regulatory agent.Used as co-matrix with DHB for MALDI-MS of sialylated glycans in negative ion mode.

Physicochemical Properties

Molecular Formula	C10H26N4
Molecular Weight	202.3402
Exact Mass	202.215
CAS #	71-44-3
Related CAS #	Spermine tetrahydrochloride;306-67-2
PubChem CID	1103
Appearance	Colorless to off-white <29°C powder,>29°C liquid
Density	0.9±0.1 g/cm3
Boiling Point	308.4±0.0 °C at 760 mmHg
Melting Point	310-311 °C (dec.)(lit.)
Flash Point	175.6±22.6 °C
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.485
LogP	-0.96
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	11
Heavy Atom Count	14
Complexity	86.1
Defined Atom Stereocenter Count	0
SMILES	N([H])(C([H])([H])C([H])([H])C([H])([H])N([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H]
InChi Key	PFNFFQXMRSDOHW-UHFFFAOYSA-N
InChi Code	InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
Chemical Name	N,N′-Bis(3-aminopropyl)-1,4-diaminobutane
Synonyms	Spermine free base, Gerontine, Musculamine, Neuridine
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	ROS-induced DNA damage is inhibited by spermine (NSC 268508) at physiologically relevant doses; peak suppression is shown at 1 to 2 mM. These concentrations fall comfortably within the range of physiological spermine concentrations that have been estimated [1].
ADME/Pharmacokinetics	Metabolism / Metabolites Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
Toxicity/Toxicokinetics	Toxicity Summary Uremic toxins such as spermine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869). Spermine is derived from spermidine by spermine synthase. Spermine is a polyamine, a small organic cations that is absolutely required for eukaryotic cell growth. Spermine, is normally found in millimolar concentrations in the nucleus. Spermine functions directly as a free radical scavenger, and forms a variety of adducts that prevent oxidative damage to DNA. Oxidative damage to DNA by reactive oxygen species is a continual problem that cells must guard against to survive. Hence, spermine is a major natural intracellular compound capable of protecting DNA from free radical attack. Spermine is also implicated in the regulation of gene expression, the stabilization of chromatin, and the prevention of endonuclease-mediated DNA fragmentation.
References	[1]. The natural polyamine spermine functions directly as a free radical scavenger. Proc Natl Acad Sci U S A. 1998 Sep 15;95(19):11140-5. [2]. Polyamines and Their Role in Virus Infection. Microbiol Mol Biol Rev. 2017 Sep 13;81(4). pii: e00029-17.
Additional Infomation	Spermine is a polyazaalkane that is tetradecane in which the carbons at positions 1, 5, 10 and 14 are replaced by nitrogens. Spermine has broad actions on cellular metabolism. It has a role as an antioxidant, an immunosuppressive agent and a fundamental metabolite. It is a polyazaalkane and a tetramine. It is a conjugate base of a spermine(4+). Spermine is a spermidine-derived biogenic polyamine found as a polycation at all pH values. Found in various tissues and organisms, it often acts as an essential growth factor in some bacterial species. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure. Spermine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Spermine has been reported in Cyanidium caldarium, Brasenia schreberi, and other organisms with data available. Spermine is a polyamine that has a similar structure to tetradecane but the carbons at positions 1, 5, 10 and 14 are replaced by nitrogens. Spermine plays a broad role in cellular metabolic processes. Spermine is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure. [PubChem] Spermine is a metabolite found in or produced by Saccharomyces cerevisiae. A biogenic polyamine formed from spermidine. It is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at all pH values. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure. See also: Hydrocarbons, terpene processing by-products (annotation moved to). Drug Indication For nutritional supplementation, also for treating dietary shortage or imbalance Mechanism of Action Spermine is derived from spermidine by spermine synthase. Spermine is a polyamine, a small organic cations that is absolutely required for eukaryotic cell growth. Spermine, is normally found in millimolar concentrations in the nucleus. Spermine functions directly as a free radical scavenger, and forms a variety of adducts that prevent oxidative damage to DNA. Oxidative damage to DNA by reactive oxygen species is a continual problem that cells must guard against to survive. Hence, spermine is a major natural intracellular compound capable of protecting DNA from free radical attack. Spermine is also implicated in the regulation of gene expression, the stabilization of chromatin, and the prevention of endonuclease-mediated DNA fragmentation. Pharmacodynamics Spermine is a polyamine. It is an organic molecule that is involved in cellular metabolism.

Solubility Data

Solubility (In Vitro)	H2O : ~125 mg/mL (~617.77 mM)
Solubility (In Vivo)	Solubility in Formulation 1: 100 mg/mL (494.22 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.9422 mL	24.7109 mL	49.4218 mL
	5 mM	0.9884 mL	4.9422 mL	9.8844 mL
	10 mM	0.4942 mL	2.4711 mL	4.9422 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.