fbpx
Wikipedia

Polyamine

January 01, 1970

Not to be confused with diamine.

A polyamine is an organic compound having more than two amino groups. Alkyl polyamines occur naturally, but some are synthetic. Alkylpolyamines are colorless, hygroscopic, and water soluble. Near neutral pH, they exist as the ammonium derivatives.[1] Most aromatic polyamines are crystalline solids at room temperature.

Natural polyamines edit

Low-molecular-weight linear polyamines are found in all forms of life. The principal examples are the triamine spermidine and the tetraamine 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).[2] Polyamines are found in high concentrations in the mammalian brain.[3]

Synthetic polyamines edit

See also: Ethyleneamines

Ethyleneamines are a commercially-important class of synthetic polyamines with ethylene (-CH2CH2- linkages); global production capacity was estimated at 385,000 tonnes in 2001.[4] They are chemical intermediates often used to make surfactants and as crosslinkers for epoxy resins.[5] Some interesting members of this class include:

Other synthetic polyamines include 1,3,5-triazinane (not to be confused with 1,3,5-triazine) and N-substituted analogs. The methylene (-CH2) linkages are derived from formaldehyde. The reaction product of monoethanolamine and formaldehyde is known industrially as "MEA triazine" (it is actually a triazinane), and it serves as a water-soluble hydrogen sulfide scavenger.[7] Hexamethylenetetramine (hexamine) is another product of formaldehyde and ammonia that has various uses in industry. Domestically, it is used as a solid camping fuel. In the laboratory, it reacts with alkyl halides to selectively prepare primary amines in the Delépine reaction.

Biological function edit

Although it is known that the biosynthesis of polyamines is highly regulated, the biological function of polyamines is only partly understood. In their cationic ammonium form, they bind to DNA, and, in structure, they represent compounds with cations that are found at regularly spaced intervals (in contrast to Mg2+
 or Ca2+
, which are point charges). They have also been found to act as promoters of programmed ribosomal frameshifting during translation.[8]

Inhibition of polyamine biosynthesis retards or stops cell growth. The provision of exogenous polyamines restores the growth of these cells. Most eukaryotic cells express a polyamine-transporting ATPase 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.[9]

Polyamines are also modulators of a variety of ion channels, including NMDA receptors and AMPA receptors. They block inward-rectifier potassium channels so that the currents of the channels are inwardly rectified, thereby the cellular energy, i.e. K+
 ion gradient across the cell membrane, is conserved. In addition, polyamine participate in initiating the expression of SOS response of Colicin E7 operon and down-regulate proteins that are essential for colicin E7 uptake, thus conferring a survival advantage on colicin-producing E. coli under stress conditions.[10]

Polyamines can enhance the permeability of the blood–brain barrier.[11]

They are involved in modulating senescence of organs in plants and are therefore considered as a plant hormone.[12] In addition, they are directly involved in regulation of programmed cell death.[13]

Homology-directed DNA repair edit

Polyamines promote homologous recombination (HR)-mediated double-strand break (DSB) repair.[14] Polyamines enhance the DNA strand exchange activity of RAD51 recombinase. Depletion of polyamines sensitizes cells to genotoxic substances such as ionizing radiation and ultraviolet radiation. The effect of polyamines on RAD51 arises from their ability to enhance the capture of homologous duplex DNA and promote RAD-51-mediated homologous DNA pairing and exchange activity.[14] Polyamines appear to have an evolutionarily conserved role in regulating recombinase activity.

Biosynthesis of spermidine, spermine, thermospermine edit

 
Biosynthesis of spermidine and spermine from putrescine. Ado = 5'-adenosyl

Spermidine is synthesized from putrescine, using an aminopropyl group from decarboxylated S-adenosyl-L-methionine (SAM), S-Adenosylmethioninamine. The reaction is catalyzed by spermidine synthase.[15]

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.[15]

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).[16]

Polyamine analogues edit

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.[17] It also decreases the expression of estrogen receptor alpha in ER-positive breast cancer.[18]

See also edit

References edit

  1. ^ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3527306732.
  2. ^ Pegg, AE; McCann, PP (1982). "Polyamine metabolism and function". American Journal of Physiology. 243 (5): 212–21. doi:10.1152/ajpcell.1982.243.5.C212. PMID 6814260. S2CID 21063248.
  3. ^ Seiler, N (1992). "Polyamines". Handbook of Neurochemistry. Vol. 1. New York, NY: Plenum Publishing Corp. pp. 223–55.
  4. ^ Srivasan Sridhar; Richard G. Carter (2001). "Diamines and Higher Amines, Aliphatic". Kirk-Othmer Encyclopedia of Chemical Technology. New York: John Wiley. doi:10.1002/0471238961.0409011303011820.a01.pub2. ISBN 9780471238966.
  5. ^ Lawrence, Stephen A. (2004). Amines: synthesis, properties and applications. Cambridge University Press. p. 64. ISBN 978-0-521-78284-5.
  6. ^ Haynes, R. K.; Vonwiller, S. C.; Luderer, M. R. (2006). "N,N,N′,N′-Tetramethylethylenediamine". In Paquette, L. (ed.). N,N,N′,N′-Tetramethylethylenediamine. Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289X.rt064.pub2. ISBN 0471936235.
  7. ^ G. N. Taylor; J. J. Wylde; T. Müller; J Murison; F. Schneider (2017). Fresh Insight into the H2S Scavenging Mechanism of MEA-Triazine vs. MMA-Triazine. SPE International Conference on Oilfield Chemistry. Montgomery, Texas. doi:10.2118/184529-MS.
  8. ^ Rato C; Amirova S.R; Bates D.G; Stansfield I; Wallace H.M (June 2011). "Translational recoding as a feedback controller: systems approaches reveal polyamine-specific effects on the antizyme ribosomal frameshift". Nucleic Acids Res. 39 (11): 4587–4597. doi:10.1093/nar/gkq1349. PMC 3113565. PMID 21303766.
  9. ^ Wang C, Delcros JG, Cannon L, et al. (November 2003). "Defining the molecular requirements for the selective delivery of polyamine conjugates into cells containing active polyamine transporters". J. Med. Chem. 46 (24): 5129–38. doi:10.1021/jm030223a. PMID 14613316.{{cite journal}}: CS1 maint: numeric names: authors list (link)
  10. ^ Yi-Hsuan Pan; Chen-Chung Liao (May 2006). "The critical roles of polyamines regulating ColE7 production and restricting ColE7 uptake of the colicin-producing Escherichia coli". J. Biol. Chem. 281 (19): 13083–13091. doi:10.1074/jbc.M511365200. PMID 16549429.
  11. ^ Zhang L, Lee HK, Pruess TH, White HS, Bulaj G (March 2009). "Synthesis and applications of polyamine amino acid residues: improving the bioactivity of an analgesic neuropeptide, neurotensin". J. Med. Chem. 52 (6): 1514–7. doi:10.1021/jm801481y. PMC 2694617. PMID 19236044.
  12. ^ Pandey S, Ranade SA, Nagar PK, Kumar N (September 2000). "Role of polyamines and ethylene as modulators of plant senescence". J. Biosci. 25 (3): 291–9. doi:10.1007/BF02703938. PMID 11022232. S2CID 21925829.
  13. ^ Moschou, PN; Roubelakis-Angelakis, KA (Nov 11, 2013). "Polyamines and programmed cell death". Journal of Experimental Botany. 65 (5): 1285–1296. doi:10.1093/jxb/ert373. PMID 24218329.
  14. ^ a b Lee CY, Su GC, Huang WY, Ko MY, Yeh HY, Chang GD, Lin SJ, Chi P. Promotion of homology-directed DNA repair by polyamines. Nat Commun. 2019 Jan 8;10(1):65. doi: 10.1038/s41467-018-08011-1. PMID 30622262; PMCID: PMC6325121
  15. ^ a b Pál M, Szalai G, Janda T (2015). "Speculation: Polyamines are important in abiotic stress signaling" (PDF). Plant Science. 237: 16–23. doi:10.1016/j.plantsci.2015.05.003. PMID 26089148.
  16. ^ Takano, A; Kakehi, J; Takahashi, T (April 2012). "Thermospermine is not a minor polyamine in the plant kingdom". Plant Cell Physiol. 53 (4): 606–16. doi:10.1093/pcp/pcs019. PMID 22366038.
  17. ^ Huang, Yi; Pledgie, Allison; Rubin, Ethel; Marton, Laurence J.; Woster, Patrick M.; Sukumar, Saraswati; Casero, Robert A.; Davidson, Nancy E. (September 2005). "Role of p53/p21(Waf1/Cip1) in the regulation of polyamine analogue-induced growth inhibition and cell death in human breast cancer cells". Cancer Biology & Therapy. 4 (9): 1006–1013. doi:10.4161/cbt.4.9.1970. PMC 3639297. PMID 16131835.
  18. ^ Huang, Y; Keen, JC; Pledgie, A; Marton, LJ; Zhu, T; Sukumar, S; Park, BH; Blair, B; Brenner, K; Casero, RA Jr; Davidson, NE (2006). "Polyamine analogues down-regulate estrogen receptor alpha expression in human breast cancer cells". J Biol Chem. 281 (28): 19055–63. doi:10.1074/jbc.M600910200. PMC 3623667. PMID 16679312.

External links edit

  • 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)

January 01, 1970
polyamine, confused, with, diamine, polyamine, organic, compound, having, more, than, amino, groups, alkyl, polyamines, occur, naturally, some, synthetic, alkylpolyamines, colorless, hygroscopic, water, soluble, near, neutral, they, exist, ammonium, derivative. Not to be confused with diamine A polyamine is an organic compound having more than two amino groups Alkyl polyamines occur naturally but some are synthetic Alkylpolyamines are colorless hygroscopic and water soluble Near neutral pH they exist as the ammonium derivatives 1 Most aromatic polyamines are crystalline solids at room temperature Contents 1 Natural polyamines 2 Synthetic polyamines 3 Biological function 3 1 Homology directed DNA repair 4 Biosynthesis of spermidine spermine thermospermine 5 Polyamine analogues 6 See also 7 References 8 External linksNatural polyamines editLow molecular weight linear polyamines are found in all forms of life The principal examples are the triamine spermidine and the tetraamine 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 2 Polyamines are found in high concentrations in the mammalian brain 3 Natural polyamines nbsp spermidine nbsp spermineSynthetic polyamines editSee also Ethyleneamines Ethyleneamines are a commercially important class of synthetic polyamines with ethylene CH2CH2 linkages global production capacity was estimated at 385 000 tonnes in 2001 4 They are chemical intermediates often used to make surfactants and as crosslinkers for epoxy resins 5 Some interesting members of this class include Ethylenediamine first member of this series It is a chelating ligand by itself and it is a precursor to the popular metal sequestrant EDTA ethylenediaminetetraacetic acid Permethylated ethylenediamine yields tetramethylethylenediamine TMEDA that has a very high affinity for lithium ions 6 Macrocyclic polyamines analogous to crown ethers 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 that is a minor side product of the polyethyleneamine process A related tripodal polyamine is 1 1 1 tris aminomethyl ethane These are interesting chelating ligands Polyethylenimine is a polymer derived from aziridine Other synthetic polyamines include 1 3 5 triazinane not to be confused with 1 3 5 triazine and N substituted analogs The methylene CH2 linkages are derived from formaldehyde The reaction product of monoethanolamine and formaldehyde is known industrially as MEA triazine it is actually a triazinane and it serves as a water soluble hydrogen sulfide scavenger 7 Hexamethylenetetramine hexamine is another product of formaldehyde and ammonia that has various uses in industry Domestically it is used as a solid camping fuel In the laboratory it reacts with alkyl halides to selectively prepare primary amines in the Delepine reaction Synthetic polyamines nbsp Tris 2 aminoethyl amine nbsp Cyclen nbsp 1 4 7 Triazacyclononane nbsp 1 1 1 Tris aminomethyl ethane nbsp Subunit of polyethylenimine nbsp Hexamethylenetetramine with its adamantane type structureBiological function editAlthough it is known that the biosynthesis of polyamines is highly regulated the biological function of polyamines is only partly understood In their cationic ammonium form they bind to DNA and in structure they represent compounds with cations that are found at regularly spaced intervals in contrast to Mg2 or Ca2 which are point charges They have also been found to act as promoters of programmed ribosomal frameshifting during translation 8 Inhibition of polyamine biosynthesis retards or stops cell growth The provision of exogenous polyamines restores the growth of these cells Most eukaryotic cells express a polyamine transporting ATPase 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 9 Polyamines are also modulators of a variety of ion channels including NMDA receptors and AMPA receptors They block inward rectifier potassium channels so that the currents of the channels are inwardly rectified thereby the cellular energy i e K ion gradient across the cell membrane is conserved In addition polyamine participate in initiating the expression of SOS response of Colicin E7 operon and down regulate proteins that are essential for colicin E7 uptake thus conferring a survival advantage on colicin producing E coli under stress conditions 10 Polyamines can enhance the permeability of the blood brain barrier 11 They are involved in modulating senescence of organs in plants and are therefore considered as a plant hormone 12 In addition they are directly involved in regulation of programmed cell death 13 Homology directed DNA repair edit Polyamines promote homologous recombination HR mediated double strand break DSB repair 14 Polyamines enhance the DNA strand exchange activity of RAD51 recombinase Depletion of polyamines sensitizes cells to genotoxic substances such as ionizing radiation and ultraviolet radiation The effect of polyamines on RAD51 arises from their ability to enhance the capture of homologous duplex DNA and promote RAD 51 mediated homologous DNA pairing and exchange activity 14 Polyamines appear to have an evolutionarily conserved role in regulating recombinase activity Biosynthesis of spermidine spermine thermospermine edit nbsp Biosynthesis of spermidine and spermine from putrescine Ado 5 adenosyl Spermidine is synthesized from putrescine using an aminopropyl group from decarboxylated S adenosyl L methionine SAM S Adenosylmethioninamine The reaction is catalyzed by spermidine synthase 15 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 15 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 16 Polyamine analogues editThe 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 17 It also decreases the expression of estrogen receptor alpha in ER positive breast cancer 18 See also editPolyamine oxidase Polyamines in plant stress Polyamine modulated factor 1References edit Eller Karsten Henkes Erhard Rossbacher Roland Hoke Hartmut 2005 Amines Aliphatic Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a02 001 ISBN 978 3527306732 Pegg AE McCann PP 1982 Polyamine metabolism and function American Journal of Physiology 243 5 212 21 doi 10 1152 ajpcell 1982 243 5 C212 PMID 6814260 S2CID 21063248 Seiler N 1992 Polyamines Handbook of Neurochemistry Vol 1 New York NY Plenum Publishing Corp pp 223 55 Srivasan Sridhar Richard G Carter 2001 Diamines and Higher Amines Aliphatic Kirk Othmer Encyclopedia of Chemical Technology New York John Wiley doi 10 1002 0471238961 0409011303011820 a01 pub2 ISBN 9780471238966 Lawrence Stephen A 2004 Amines synthesis properties and applications Cambridge University Press p 64 ISBN 978 0 521 78284 5 Haynes R K Vonwiller S C Luderer M R 2006 N N N N Tetramethylethylenediamine In Paquette L ed N N N N Tetramethylethylenediamine Encyclopedia of Reagents for Organic Synthesis New York J Wiley amp Sons doi 10 1002 047084289X rt064 pub2 ISBN 0471936235 G N Taylor J J Wylde T Muller J Murison F Schneider 2017 Fresh Insight into the H2S Scavenging Mechanism of MEA Triazine vs MMA Triazine SPE International Conference on Oilfield Chemistry Montgomery Texas doi 10 2118 184529 MS Rato C Amirova S R Bates D G Stansfield I Wallace H M June 2011 Translational recoding as a feedback controller systems approaches reveal polyamine specific effects on the antizyme ribosomal frameshift Nucleic Acids Res 39 11 4587 4597 doi 10 1093 nar gkq1349 PMC 3113565 PMID 21303766 Wang C Delcros JG Cannon L et al November 2003 Defining the molecular requirements for the selective delivery of polyamine conjugates into cells containing active polyamine transporters J Med Chem 46 24 5129 38 doi 10 1021 jm030223a PMID 14613316 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint numeric names authors list link Yi Hsuan Pan Chen Chung Liao May 2006 The critical roles of polyamines regulating ColE7 production and restricting ColE7 uptake of the colicin producing Escherichia coli J Biol Chem 281 19 13083 13091 doi 10 1074 jbc M511365200 PMID 16549429 Zhang L Lee HK Pruess TH White HS Bulaj G March 2009 Synthesis and applications of polyamine amino acid residues improving the bioactivity of an analgesic neuropeptide neurotensin J Med Chem 52 6 1514 7 doi 10 1021 jm801481y PMC 2694617 PMID 19236044 Pandey S Ranade SA Nagar PK Kumar N September 2000 Role of polyamines and ethylene as modulators of plant senescence J Biosci 25 3 291 9 doi 10 1007 BF02703938 PMID 11022232 S2CID 21925829 Moschou PN Roubelakis Angelakis KA Nov 11 2013 Polyamines and programmed cell death Journal of Experimental Botany 65 5 1285 1296 doi 10 1093 jxb ert373 PMID 24218329 a b Lee CY Su GC Huang WY Ko MY Yeh HY Chang GD Lin SJ Chi P Promotion of homology directed DNA repair by polyamines Nat Commun 2019 Jan 8 10 1 65 doi 10 1038 s41467 018 08011 1 PMID 30622262 PMCID PMC6325121 a b Pal M Szalai G Janda T 2015 Speculation Polyamines are important in abiotic stress signaling PDF Plant Science 237 16 23 doi 10 1016 j plantsci 2015 05 003 PMID 26089148 Takano A Kakehi J Takahashi T April 2012 Thermospermine is not a minor polyamine in the plant kingdom Plant Cell Physiol 53 4 606 16 doi 10 1093 pcp pcs019 PMID 22366038 Huang Yi Pledgie Allison Rubin Ethel Marton Laurence J Woster Patrick M Sukumar Saraswati Casero Robert A Davidson Nancy E September 2005 Role of p53 p21 Waf1 Cip1 in the regulation of polyamine analogue induced growth inhibition and cell death in human breast cancer cells Cancer Biology amp Therapy 4 9 1006 1013 doi 10 4161 cbt 4 9 1970 PMC 3639297 PMID 16131835 Huang Y Keen JC Pledgie A Marton LJ Zhu T Sukumar S Park BH Blair B Brenner K Casero RA Jr Davidson NE 2006 Polyamine analogues down regulate estrogen receptor alpha expression in human breast cancer cells J Biol Chem 281 28 19055 63 doi 10 1074 jbc M600910200 PMC 3623667 PMID 16679312 External links editPolyamines 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 Retrieved from https en wikipedia org w index php title Polyamine amp oldid 1218062251, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.