71-44-3 Usage
Description
Spermine is an endogenous polyamine synthesized from the reaction of spermidine with decarboxylated S-adenosylmethionine in the presence of the enzyme spermine synthase and is required for eukaryotic cell growth and protein synthesis. Intracellular spermine blocks inward rectifying K+ channels, whereas extracellular spermine acts as a mixed NMDA glutamate receptor agonist/antagonist at the polyamine site. Spermine has neuroprotective and anti-inflammatory effects and functions as a free radical scavenger to prevent DNA damage by reactive oxygen species.
Chemical Properties
White to slightly off-white powder crysta
Uses
Different sources of media describe the Uses of 71-44-3 differently. You can refer to the following data:
1. immune modulator
2. Binds to the polyamine modulatory site of NMDA Spermine is essential for both normal and neoplastic tissue growth. It is involved in the modulation of calcium-dependent immune processes. It plays an important role in cellular proliferation and differentiation as well as inhibits neuronal nitric oxide synthase (nNOS).
3. Biogenic polyamine formed from spermidine and occurring in almost all tissues. Essential for both normal and neoplastic tissue growth. Involved in the modulation of calcium-dependent immune processes
Definition
ChEBI: 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.
General Description
Spermine?is a polyamine, which functions as a free radical scavenger. It modulates gene expression, chromatin stabilization and prevents DNA damage. Spermine inhibits endonuclease-mediated DNA fragmentation.
Biochem/physiol Actions
Mixed NMDA glutamate receptor 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).
references
[1] fakler b, brndle u, glowatzki e, et al. strong voltage-dependent inward rectification of inward rectifier k+ channels is caused by intracellular spermine[j]. cell, 1995, 80(1): 149-154.[2] til h p, falke h e, prinsen m k, et al. acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats[j]. food and chemical toxicology, 1997, 35(3): 337-348.
Check Digit Verification of cas no
The CAS Registry Mumber 71-44-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 1 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 71-44:
(4*7)+(3*1)+(2*4)+(1*4)=43
43 % 10 = 3
So 71-44-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2/p+4
71-44-3Relevant articles and documents
Practical synthesis of spermine, thermospermine and norspermine
Kariya, Yuka,Asanuma, Yuta,Inai, Makoto,Asakawa, Tomohiro,Ohashi-Ito, Kyoko,Fukuda, Hiroo,Egi, Masahiro,Kan, Toshiyuki
, p. 1403 - 1407 (2016/09/09)
Polyamines, such as spermine (1), thermospermine (2) and norspermine (3), are widely distributed in nature, and have multiple biological activities. In addition, many of their conjugates have potential for pharmacological use. Here, we present a solid-phase synthesis using our nitrobenzenesulfonyl (Ns) strategy, which can provide 1, 2 and 3 on a gram scale. This approach should be suitable for facile construction of a diverse library of polyamines.
Crystal structures and enzymatic properties of a triamine/agmatine aminopropyltransferase from thermus thermophilus
Ohnuma, Mio,Ganbe, Tadashi,Terui, Yusuke,Niitsu, Masaru,Sato, Takao,Tanaka, Nobuo,Tamakoshi, Masatada,Samejima, Keijiro,Kumasaka, Takashi,Oshima, Tairo
experimental part, p. 971 - 986 (2012/05/20)
To maintain functional conformations of DNA and RNA in high-temperature environments, an extremely thermophilic bacterium, Thermus thermophilus, employs a unique polyamine biosynthetic pathway and produces more than 16 types of polyamines. In the thermophile genome, only one spermidine synthase homolog (SpeE) was found and it was shown to be a key enzyme in the pathway. The catalytic assay of the purified enzyme revealed that it utilizes triamines (norspermidine and spermidine) and agmatine as acceptors in its aminopropyl transfer reaction; therefore, the enzyme was denoted as a triamine/agmatine aminopropyltransferase (TAAPT). We determined the crystal structures of the enzyme complexed with and without the aminopropyl group donor S-adenosylmethionine. Despite sequence and structural similarity with spermidine synthases from other organisms, a novel C-terminal β-sheet and differences in the catalytic site were observed. The C-terminal module interacts with the gatekeeping loop and fixes the open conformation of the loop to recognize larger polyamine substrates such as agmatine and spermidine. Additional computational docking studies suggest that the structural differences of the catalytic site also contribute to recognition of the aminopropyl/aminobutyl or guanidium moiety of the substrates of TAAPT. These results explain in part the extraordinarily diverse polyamine spectrum found in T. thermophilus.
Chemoenzymatic syntheses of polyamines and tetraazamacrocycles
Rubio, Mercedes,Astorga, Covadonga,Alfonso, Ignacio,Rebolledo, Francisca,Gotor, Vicente
, p. 2441 - 2452 (2007/10/03)
Syntheses of different open chain polyamines starting from enzymatically prepared bis(amidoesters) are described. Some of these polyamines are also used as precursors in the syntheses of tetraazamacrocycles. This methodology can also be applied to the synthesis of chiral compounds.
