Polyamine

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A polyamine is an organic compound having two or more primary amino groups -NH2.

This class of compounds includes several synthetic substances that are important feedstocks for the chemical industry, such as ethylene diamine H2N-CH2-CH2-NH2, 1,3-diaminopropane H2N-(CH2)3-NH2, and hexamethylenediamine H2N-(CH2)6-NH2. It also includes many substances that play important roles in both eukaryotic and prokaryotic cells, such as putrescine H2N-(CH2)4-NH2, cadaverine H2N-(CH2)5-NH2, spermidine H2N-((CH2)4-NH-)2-H, and spermine H2N-((CH2)4-NH-)3-H.

As of 2004, there had been no reports of any geminal diamine, a compound with two or more unsubstituted -NH2 groups on the same carbon atom. However, substituted derivatives are known, such as tetraethylmethylenediamine, (C2H5)2N-CH2-N(C2H5)2.[1]

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

Contents

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.[2]

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