Spermine

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Spermine
Skeletal formula of spermine
Ball and stick model of spermine
Spacefill model of spermine
Identifiers
3D model (JSmol)
3DMet B01325
1750791
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.000.686
EC Number 200-754-2
454653
KEGG
MeSH Spermine
RTECS number EJ7175000
UN number 3259
Properties
C10H26N4
Molar mass 202.35 g·mol−1
Appearance Colourless crystals
Odor Ichtyal, ammoniacal
Density 937 mg mL−1
Melting point 28 to 30 °C (82 to 86 °F; 301 to 303 K)
Boiling point 150.1 °C; 302.1 °F; 423.2 K at 700 Pa
log P −0.543
Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H314
P280, P305+351+338, P310
Flash point 110 °C (230 °F; 383 K)
Related compounds
Related compounds
Spermidine, Putrescine, Cadaverine, Diethylenetriamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. It is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, particularly in viruses.

Crystals of spermine phosphate were first described in 1678, in human semen, by Antonie van Leeuwenhoek.[1] The name spermin was first used by the German chemists Ladenburg and Abel in 1888,[2] and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling)[3] and Germany (by Wrede et al.).[4] Spermine is the chemical primarily responsible for the characteristic odor of semen.[5]

Derivative[edit]

A derivative of spermine, N1, N12-bis(ethyl)spermine (also known as BESm) was investigated in the late 1980s along with similar polyamine analogues for its potential as a cancer therapy.[6][7]

Biosynthesis[edit]

Spermine biosynthesis from animals starts from the conversion of L-Ornithine to putrescine by PLP and through two consecutive action of N-alkylation with decarboxylated SAM, spermine is synthesized. Plants have different routes to biosynthesize spermine. One of the route converts L-Glutamine to L-Ornithine and then L-Ornithine follows the same pathway as in animals to spermine.

biosynthetic mechanism for spermine in animals

Another pathway in plants starts from L-Arginine. It is first decarboxylated, followed by hydrolysis of the imine functional group in a guanidine system to produce N-carbamoylputrescine. Then N-carbamoylputrescine is hydrolyzed to produce putrescine with urea as a byproduct.

alternative biosynthetic mechanism for spermine in plants

[8]

References[edit]

  1. ^ Leeuwenhoek, A. van (1678) Observationes D. Anthonii Leeuwenhoek, de natis e semine genitali animalculis. Letter dated November 1677. Philos. Trans. Roy. Soc. London, 12,1040-1043.
  2. ^ Ladenburg A., Abel J. (1888) Über das Aethylenimin (Spermin?). Ber. Dtsch. chem. Ges. 21: 758-766
  3. ^ Dudley H. W., Rosenheim O., Starling W. W. (1926) The chemical constitution of spermine. III.Structure and synthesis. Biochemical Journal 20(5): 1082-1094
  4. ^ Wrede F. (1925) Über die aus menschlichem Sperma isolierte Base Spermin. Dtsch. Med. Wochenschr. 51: 24
  5. ^ Klein, David (2013). Organic Chemistry (2nd ed.). 
  6. ^ Porter, Carl W.; McManis, Jim; Casero, Robert A.; Bergeron, Raymond J. (1987). "Relative Abilities of Bis(ethyl) Derivatives of Putrescine, Spermidine, and Spermine to Regulate Polyamine Biosynthesis and Inhibit L1210 Leukemia Cell Growth" (PDF). Cancer Research. 47: 2821–2825. 
  7. ^ Pegg, Anthony E.; Wechter, Rita; Pakala, Rajbabu; Bergeron, Raymond J. (1989). "Effect of N1, N12-Bis(ethyl)spermine and Related Compounds on Growth and Polyamine Acetylation, Content, and Excretion in Human Colon Tumor Cells" (PDF). Journal of Biological Chemistry. 264 (20): 11744–11749. 
  8. ^ Dewick, Paul M (2009). Medicinal Natural Products: a biosynthetic approach (3rd ed.). Chichester U.K.: Wiley. p. 312. ISBN 9780470742761. 

Further reading[edit]

  • Slocum, R. D., Flores, H. E., "Biochemistry and Physiology of Polyamines in Plants", CRC Press, 1991, USA, ISBN 0-8493-6865-0
  • Uriel Bachrach, "The Physiology of Polyamines", CRC Press, 1989, USA, ISBN 0-8493-6808-1