Polyamine

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The polyamines are organic compounds having two or more primary amino groups - such as putrescine, cadaverine, spermidine, and spermine - that are growth factors in both eucaryotic and procaryotic cells.

Cyclen is the main representative of a class of cyclic polyamines. Polyethylene amine is a polymer based on aziridine monomer.

Contents 1 Functions 2 Synthesis of linear polyamines 2.1 Putrescine 2.2 Cadaverine 2.3 Spermidine and spermine 3 References 4 External links

Functions

Though it is known that polyamines are synthesized in cells via highly-regulated pathways, their actual function is not entirely clear. As cations, they bind to DNA, and, in structure, they represent compounds with cations that are found at regularly-spaced intervals (unlike, say, Mg⁺⁺ or Ca⁺⁺, which are point charges).

If cellular polyamine synthesis is inhibited, cell growth is stopped or severely retarded. The provision of exogenous polyamines restores the growth of these cells. Most eukaryotic cells have a polyamine transporter system on their cell membrane that facilitates the internalization of exogenous polyamines. This system is highly active in rapidly proliferating cells and is the target of some chemotherapeutics currently under development.^[1]

Polyamines are also important modulators of a variety of ion channels, including NMDA receptors, AMPA receptors, and Inward-rectifier potassium ion channels.

Synthesis of linear polyamines

Putrescine

Putrescine is synthesized biologically via two different pathways, both starting from arginine.

• In one pathway, arginine is converted into agmatine, with a reaction catalyzed by the enzyme arginine decarboxylase (ADC); then agmatine is transformed into carbamilputrescine by agmatine imino hydroxylase (AIH). Finally, carbamilputrescine is converted into putrescine.
• In the second pathway, arginine is converted into ornithine and then ornithine is converted into putrescine by ornithine decarboxylase (ODC).

Cadaverine

Cadaverine is synthesized from lysine in a one-step reaction with lysine decarboxylase (LDC).

Spermidine and spermine

Spermidine is synthesized from putrescine, using an aminopropylic group from decarboxylated S-adenosyl-L-methionine (SAM). The reaction is catalyzed by spermidine synthase.

Spermine is synthesized from the reaction of spermidine with SAM in the presence of the enzyme spermine synthase .

Image:SPD SPM synthesis.jpg

References

1. ↑ Wang, C.; Delcros, J.-G.; Cannon, L.; Konate, F.; Carias, H.; Biggerstaff, J.; Gardner, R.; Phanstiel, O. Defining the molecular requirements for the selective delivery of polyamine-conjugates into cells containing active polyamine transporters. J. Med. Chem. 2003, 46, 5129-5138.

External links

• Polyamines in cell cycle proliferation and cell death

• Ornithine Decarboxylase: Expression and regulation in rat brain and in transgenic mice, 2002, Pekka Kilpelainen, Department of Biochemistry, University of Oulu. Extensive review of literature through 2001 on polyamine structure, properties, metabolism in mammals, and physiological and pathophysiological roles (See article Table of Contents)

Template:Plant hormonesde:Polyamine it:Poliammine he:פוליאמין