Amines spermidine

Species of Pseudomonas can utilize the a,(i)-diamines putrescine, spermidine, and spermine as sources of carbon and nitrogen, and putrescine can be produced from the secondary amine spermidine together with 1,3-diaminopropane (Dasu et al. 2006). Putrescine (1,4-diaminobutane) is an intermediate in the arginine decarboxylase (ADC) pathway of L-arginine degradation, which is described later, and can be degraded, by two pathways ... 

The amines spermidine, spermine, and putrescine, which are all hydro-philes, act synergistically with malathion, a lipophile, to inhibit cholinesterase activity in toads. 

An accurate and very sensitive method was developed for the simultaneous determination of the diamines (1,3-diaminopropane (DAP), putrescine (Pu), and try amine), poly amines (spermidine and spermine), and of the aromatic amines ( 3-phenylethylamine and tyramine) found in pool wines and grape juices.This method combines a simple ion-pair extraction... 

Biologically active polyamines putrescine, spermidine and spermine, differ from the traditional group of biogenic amines. Spermidine and spermine arise under specific conditions and they also have different biological effects in comparison with the classical biogenic amines, which are mainly histamine, tyramine, 2-phenylethylamine, putrescine, cadaverine, tryptamine and agmatine. 

Mandal S, Mandal A, Johansson HE et al (2013) Depletion of cellular poly amines, spermidine and spermine, causes a total arrest in translation and growth in mammalian cells. Proc Natl Acad... 

Ac2NOMe selectively acylates a primary amine of a spermidine. ... 

The polyamines putrescine, cadaverine, spermidine, and spermine, which are seen at elevated levels in some victims of cancer, were separated on a Technicon (The Technicon Company Chauncey, NY) TSM Amino Acid Analyzer packed with an 8% divinylbenzene-co-polystyrene sulfonated resin with post-column ninhydrin detection.111 Amines such as ethanolamine, noradrenaline, hexamethylene diamine, methoxytryptamine, spermine, and spermidine were separated from amino acids on a DC-4A cation exchange resin.112 A similar approach, using a Beckman Model 121M amino acid analyzer equipped with an AA-20 column, was also successful.113 A Polyamin-pak strong cation exchange column (JASCO) was eluted with a citrate buffer for the detection of putrescene, spermine, cadaverine, and 1,5-diaminohex-ane from rat thymus.114 A post-column o-phthaldehyde detection system was used. 

IEC was applied to determine biogenic polyamines such as putrescine (4a), cadaverine (4b), tyramine (5), histamine (6), spermidine (38), agmatine (39) and tryptamine (40), contained in aqueous trichloroacetic extracts of leafy vegetables, such as cabbage and lettuce. A cation exchange column loaded with potassium ions and a special buffer were used. Spermidine (38) was the major amine detected in this group (7-15 Xg/g fresh weight)144. 

At physiological pH, polyamines are fully protonated and polycationic. It is possible that the amino group of amines prevents SAM from reacting with ACS by interfering with the prosthetic groups of the enzyme. Polyamines such as putrescine, spermidine, and spermine, and methionine cycle intermediates such as MTA and KMB have been shown to have an inhibitory effect on ACS activity. ... 

Later, Chu and Bjeldanes (53) showed that the binding histamine to mucin could be inhibited in vitro by spermine, spermidine, putrescine, cadaverine, and a basic extract of tuna. The inhibition required relatively high amine concentrations, and the concentrated tuna extract exerted only a 23% inhibition of binding ( ). Each mole of intestinal mucin can bind 2.5 moles of histamine (53). 

The venoms of many kinds of bees, wasps, and hornets (the genera Vespa, Polistes, Vespula, Ropalidia, etc.) contain biogenic amines such as histamine (136), serotonin (141), and catecholamines in addition to polyamines such as putrescine (111), spermidine (110), and spermine (112) (Table VIII). The biogenic amines in the venoms act as the main pain-producing principles 46). The contents of these amines in the venom may affect the severity of pain production, edematous reaction of the skin, or increase in skin permeability by stings of these insects. Consequently these amines act as toxins for their defense, together with acetylcholine, enzymes, and peptides 47). 

Three acyclic amines, dimethylamine (109), putrescine (111), and spermidine (110), have been isolated from the accessary sexual glands of the mature male desert locust, Schistocerca gregaria (Table VIII). In addition, A -pyrroline (12i) has been identified as a volatile emanating from the mature male locust colony (Table II). It is an oxidation product of putrescine and probably could be responsible for the maturation-accelerating effect observed to be specific to the mature male insect 106). 

Polyamine oxidase (amine oxygen oxidoreductase, deaminating, flavin-containing), is also a FAD-dependent enzyme and has many similarities to MAO. It is responsible for the oxidation of the secondary amino group in such substrates as A/-acetyl spermine and spermidine in the biosynthesis of spermidine and putrescine [1,12], This enzyme will not be covered in this chapter. 

The aminopropylation of spermidine into spermine by spermine synthase (SPM synthase) is favored by a higher basicity (ease of protonation) of the nitrogens N-1 and N-4, but also by a lower basicity of N-8 of the butylamino terminal group (more difficult protonation). This last factor enhances the affinity of the substrate for the enzyme. Fluorospermidines could then appear as potential inhibitors of SPM synthase. Indeed, the presence of fluorine atoms in P of an amino group lowers the basicity of the amine the pK value of N-4 is lowered by 2.70 units for... 

Figure 4.5 Reductive amination of 1 with Boc protected spermidine and spermine. Reprinted from reference [2], with permission from Elsevier.

Subsequently, the phthalylglutamic acid (Fig. 7.75), a dicarboxylic acid, was shown to be teratogenic in mice when given on days 7 to 9 of pregnancy. However, other work has indicated that the phthalimide ring is of importance in the teratogenicity. Other studies have indicated that thalidomide acylates aliphatic amines such as putrescine and spermidine, histones, RNA, and DNA and that it may also affect ribosomal integrity. 

Other BAs, such as putrescine (Put), cadaverine (Cad), tryptamine (Try), /3-phenylethyl-amine (Phe), spermine (Spm), and spermidine (Spd), have been described as potentiators that enhance the toxicity of His (21,22) likewise, Tyr and Phe are thought to precipitate migraine attacks in susceptible subjects (23). 

Polyamines like spermidine and spermine, which bind tightly to nucleic acids and are abundant in rapidly proliferating cells, are present in parasitic helminths in amounts comparable to those in vertebrate cells. As the enzymes necessary for their synthesis are lacking in adult parasitic flatworms, it is assumed that these compounds are obtained from the host (Bacchi and Yarlett, 1 995). In F. hepatica a polyamine N-acetyltransferase has been characterized, that is thought to play a major role in the polyamine metabolism of this parasite by inactivating excess amines (Aisien and Walter, 1993). 

Draisci et al. [7] Biogenic amines putrescine, cadaverine, histamine, tyramine, spermidine, spermine, tryptamine Anchovies Diamine oxidase (DAO)/on a nylon-net membrane, using glutaraldehyde Platinum electrode/ +0.650V vs. Ag/AgCl ... 

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