Espermidina

Espermidina
	Skeletal formula of spermidine
	Ball and stick model of spermidine
	Nome IUPAC N-(3-aminopropil)butano-1,4-diamina.
Identificadores
Número CAS	124-20-9
PubChem	1102
ChemSpider	1071
Número CE	204-689-0
Número UN	2735
DrugBank	DB03566
KEGG	C00315
MeSH	Spermidine
ChEBI	CHEBI:16610
ChEMBL	CHEMBL19612
Ligando IUPHAR	2390
Número RTECS	EJ7000000
Referencia Beilstein	1698591
Referencia Gmelin	454510
3DMet	B01214
Imaxes 3D Jmol	Image 1
	SMILES NCCCCNCCCN ;
	InChI InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2; Key: ATHGHQPFGPMSJY-UHFFFAOYSA-N;
Propiedades
Fórmula molecular	C7H19N3
Masa molar	145,25 g mol−1
Aspecto	Líquido incoloro
Olor	a peixe, amoniacal
Densidade	925 mg mL−1
Punto de fusión	22-25 °C
Solubilidade en auga	145 g L−1 (a 20 °C)
log P	−0,504
λmax	260 nm
Absorbancia	0,1
Índice de refracción (nD)	1,479
Perigosidade
Palabra sinal GHS	DANGER
declaración de perigosidade GHS	H314
declaración de precaución GHS	P280, P305+351+338, P310
Clasificación da UE	C
Frases R	R34
Frases S	s26, s36/37/39
Punto de inflamabilidade	112 °C; 234 °F; 385 K
Compostos relacionados
aminas relacionados	Dipropilamina, Metil-n-amilnitrosamina, Norspermidina, Dibutilamina, Iproheptina
	; Se non se indica outra cousa, os datos están tomados en condicións estándar de 25 °C e 100 kPa.

A espermidina é unha poliamina implicada no metabolismo celular e atopada en case todos os tecidos asociada aos ácidos nucleicos. Trátase dunha poliamina lineal con tres grupos amínicos coa fórmula H₂N-((CH₂)₄-NH-)₂-H. A pH fisiolóxico a espermidina está ionizada en forma policatiónica. A espermidina sintetízase a partir da putrescina por reacción coa S-adenosil metionina descarboxilada en reacción catalizada pola espermidina sintase. A partir da espermidina pode sintetizarse a espermina ^[1].

Funcións e aplicacións

Entre as funcións coñecidas da espermidina están as seguintes:

Axuda a estabilizar os ácidos nucleicos.
Inhibición da óxido nítrico sintase neuronal (nNOS ou NOS1)^[2]
Axuda no proceso in vitro de transcrición do ARN por estimulación da actividade da polinucleótido quinase do bacteriófago T4 e a ARN polimerase T7 ^[3].
Únese e fai precipitar o ADN e utilízase na purificación de proteínas de unión ao ADN ^[4]
Regulación e promoción do crecemento das plantas, xa que as poliaminas reguladoras do crecemento das plantas funcionan tamén como hormonas vexetais que promoven a embrioxénese somática.^[5]^[6]^[7]^[8]^[9]^[10]^[11]
Tamén se encontrou que a espermidina reduce o envellecemento dos lévedos, moscas, vermes, e células inmunitarias humanas ao inducir a autofaxia.^[12]
A espermidina pode utilizarse en electroporación durante a transferencia de ADN ao interior da célula con impulsos eléctricos ^[13].
Estimulación da autofaxia. Recentemente Tirupathi Pichiah et.al., suxeriron que a espermina podía ser útil para tratar a diabetes tipo 2 ^[14].

Notas

↑ PubChem Compound Spermidine
↑ Hu J., Mahmoud M.I., el-Fakahany E.E., Polyamines inhibit nitric oxide synthase in rat cerebellum. Neurosci. Lett. 1994, 175, 41-5.
↑ Lillehaug J. R., Kleppe K. Effect of salts and polyamines on T4 polynucleotide kinase. [1]
↑ Wan C.Y., Wilkins T.A., Spermidine facilitates PCR amplification of target DNA. PCR Methods Appl. 1993, 3, 208-10.
↑ Cull M., McHenry C.S., Preparation of extracts from prokaryotes. Methods Enzymol. 1990, 182, 147-53.
↑ Blethen S.L., Boeker E.A., Snell E.E., Arginine decarboxylase from Escherichia coli. I. Purification and specificity for substrates and coenzyme. J. Biol. Chem. 1968, 243, 1671-7.
↑ Wu W.H., Morris D.R., Biosynthetic arginine decarboxylase from Escherichia coli. Subunit interactions and the role of magnesium ion. J. Biol. Chem. 1973, 248, 1696-9.
↑ Tabor C.W., Tabor H., Polyamines. Annu. Rev. Biochem. 1984, 53, 749-90.
↑ Krug M.S., Berger S.L., First-strand cDNA synthesis primed with oligo(dT). Methods Enzymol. 1987, 152, 321-25.
↑ Karkas J.D., Margulies L., Chargaff E., A DNA polymerase from embryos of Drosophila melanogaster. Purification and properties. J. Biol. Chem. 1975, 250, 8657-63.
↑ Bouché J.P., The effects of spermidine on endonuclease inhibition by agarose contaminants. Anal. Biochem. 1981, 115, 42-5.
↑ name=Nature Cell Biology>Tobias Eisenberg, Heide Knauer, Alexandra Schauer, Sabrina Büttner, Christoph Ruckenstuhl, Didac Carmona-Gutierrez, Julia Ring, Sabrina Schroeder, Christoph Magnes, Lucia Antonacci, Heike Fussi, Luiza Deszcz, Regina Hart, Elisabeth Schraml, Alfredo Criollo, Evgenia Megalou, Daniela Weiskopf, Peter Laun, Gino Heeren, Michael Breitenbach, Beatrix Grubeck-Loebenstein, Eva Herker, Birthe Fahrenkrog, Kai-Uwe Fröhlich, Frank Sinner, Nektarios Tavernarakis, Nadege Minois, Guido Kroemer, Frank Madeo (4 October 2009). "Induction of autophagy by spermidine promotes longevity,". Nature Cell Biology 11 (11). doi:10.1038/ncb1975.
↑ Maren Bell and Robert Mortimer, Human Genome Center, Division of Cell and Molecular Biology, Lawrence Berkeley Laboratory, Berkeley, California 94720 Electroporation Of Yeast Artificial Chromosomes [2]
↑ Tirupathi Pichiah, PB; Suriyakalaa, U, Kamalakkannan, S, Kokilavani, P, Kalaiselvi, S, SankarGanesh, D, Gowri, J, Archunan, G, Cha, YS, Achiraman, S (2011 Oct). "Spermidine may decrease ER stress in pancreatic beta cells and may reduce apoptosis via activating AMPK dependent autophagy pathway.". Medical hypotheses 77 (4): 677–9. PMID 21831529.

Véxase tamén

Outros artigos

Ligazóns externas

Safety Data Sheet Arquivado 28 de setembro de 2011 en Wayback Machine.

[1] PubChem Compound Spermidine

[2] Hu J., Mahmoud M.I., el-Fakahany E.E., Polyamines inhibit nitric oxide synthase in rat cerebellum. Neurosci. Lett. 1994, 175, 41-5.

[3] Lillehaug J. R., Kleppe K. Effect of salts and polyamines on T4 polynucleotide kinase. [1]

[4] Wan C.Y., Wilkins T.A., Spermidine facilitates PCR amplification of target DNA. PCR Methods Appl. 1993, 3, 208-10.

[5] Cull M., McHenry C.S., Preparation of extracts from prokaryotes. Methods Enzymol. 1990, 182, 147-53.

[6] Blethen S.L., Boeker E.A., Snell E.E., Arginine decarboxylase from Escherichia coli. I. Purification and specificity for substrates and coenzyme. J. Biol. Chem. 1968, 243, 1671-7.

[7] Wu W.H., Morris D.R., Biosynthetic arginine decarboxylase from Escherichia coli. Subunit interactions and the role of magnesium ion. J. Biol. Chem. 1973, 248, 1696-9.

[8] Tabor C.W., Tabor H., Polyamines. Annu. Rev. Biochem. 1984, 53, 749-90.

[9] Krug M.S., Berger S.L., First-strand cDNA synthesis primed with oligo(dT). Methods Enzymol. 1987, 152, 321-25.

[10] Karkas J.D., Margulies L., Chargaff E., A DNA polymerase from embryos of Drosophila melanogaster. Purification and properties. J. Biol. Chem. 1975, 250, 8657-63.

[11] Bouché J.P., The effects of spermidine on endonuclease inhibition by agarose contaminants. Anal. Biochem. 1981, 115, 42-5.

[12] =Nature Cell Biology>Tobias Eisenberg, Heide Knauer, Alexandra Schauer, Sabrina Büttner, Christoph Ruckenstuhl, Didac Carmona-Gutierrez, Julia Ring, Sabrina Schroeder, Christoph Magnes, Lucia Antonacci, Heike Fussi, Luiza Deszcz, Regina Hart, Elisabeth Schraml, Alfredo Criollo, Evgenia Megalou, Daniela Weiskopf, Peter Laun, Gino Heeren, Michael Breitenbach, Beatrix Grubeck-Loebenstein, Eva Herker, Birthe Fahrenkrog, Kai-Uwe Fröhlich, Frank Sinner, Nektarios Tavernarakis, Nadege Minois, Guido Kroemer, Frank Madeo (4 October 2009). "Induction of autophagy by spermidine promotes longevity,". Nature Cell Biology 11 (11). doi:10.1038/ncb1975.

[13] Maren Bell and Robert Mortimer, Human Genome Center, Division of Cell and Molecular Biology, Lawrence Berkeley Laboratory, Berkeley, California 94720 Electroporation Of Yeast Artificial Chromosomes [2]

[14] Tirupathi Pichiah, PB; Suriyakalaa, U, Kamalakkannan, S, Kokilavani, P, Kalaiselvi, S, SankarGanesh, D, Gowri, J, Archunan, G, Cha, YS, Achiraman, S (2011 Oct). "Spermidine may decrease ER stress in pancreatic beta cells and may reduce apoptosis via activating AMPK dependent autophagy pathway.". Medical hypotheses 77 (4): 677–9. PMID 21831529.

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