The principal examples are the triamine and tetraamine spermidine and spermine. They are structurally and biosynthetically related to the diamines putrescine and cadaverine. Polyamine metabolism is regulated by the activity of the enzyme ornithine decarboxylase (ODC).Polyamine is an organic compound having more than two amino groups. Alkyl polyamines occur naturally but are also synthetic. Alkylpolyamines are colorless, hygroscopic, and water soluble. Near neutral pH, they exist as the ammonium derivatives. Most aromatic polyamines are crystalline solids at room temperature.
Low-molecular-weight linear polyamines are found in all forms of life. The principal examples are the triamine and tetraamine spermidine and spermine. They are structurally and biosynthetically related to the diamines putrescine and cadaverine. Polyamine metabolism is regulated by the activity of the enzyme ornithine decarboxylase (ODC). Polyamines are found in high concentrations in the mammalian brain.
Several synthetic polyamines are used in chemical industry and the research laboratory. They are mainly of interest as additives to motor oil and as co-reactants (hardeners) with epoxy resins. Many synthetic polyamines feature NCH2CH2N linkages:
Diethylenetriamine, abbreviated dien or DETA, (H2N-CH2CH2-NH-CH2CH2-NH2. The related permethylated derivative pentamethyldiethylenetriamine is used as a chelating agent in organolithium chemistry.
Triethylenetetramine (trien or TETA, H2N-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH2), tetraethylenepentamine (TEPA, H2N-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH2), pentaethylenehexamine (PEHA, H2N-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH2).
Macrocyclic polyamines: 1,4,7-triazacyclononane ((NHCH2CH2)3) and cyclen ((NHCH2CH2)4). A related tetraaza macrocycle is cyclam.
Tris(2-aminoethyl)amine (N(CH2CH2NH2)3) is a branched polyamine. A related tripodal polyamine is 1,1,1-tris(aminomethyl)ethane.
Biosynthesis of spermidine, spermine, thermospermine
Spermidine is synthesized from putrescine, using an aminopropyl 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.
The polyamines undergo rapid interconversion in the polyamine cycle, in which putrescine leads to synthesis of spermidine and spermine, with degradation of these polyamines to form putrescine, which can begin the cycle again.
Thermospermine (NH2-(CH2)3-NH-(CH2)3-NH-(CH2)4-NH2) is a structural isomer of spermine and a novel type of plant growth regulator. It is produced from spermidine by the action of thermospermine synthase, which is encoded by a gene named ACAULIS5 (ACL5).
The critical role of polyamines in cell growth has led to the development of a number of agents that interfere with polyamine metabolism. These agents are used in cancer therapy. Polyamine analogues upregulate p53 in a cell leading to restriction of proliferation and apoptosis. It also decreases the expression of estrogen receptor alpha in ER-positive breast cancer.
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