Spermine
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| Identifiers | |
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3D model (JSmol)
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| 3DMet | |
| 1750791 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.000.686 |
| EC Number |
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| 454653 | |
| KEGG | |
| MeSH | Spermine |
PubChem CID
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| RTECS number |
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| UN number | 3259 |
CompTox Dashboard (EPA)
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| Properties | |
| C10H26N4 | |
| Molar mass | 202.346 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 labelling: | |
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| Danger | |
| H314 | |
| P280, P305+P351+P338, P310 | |
| Flash point | 110 °C (230 °F; 383 K) |
| Related compounds | |
Related compounds
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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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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
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]
References
- ^ 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.
- ^ Ladenburg A., Abel J. (1888) Über das Aethylenimin (Spermin?). Ber. Dtsch. chem. Ges. 21: 758-766
- ^ Dudley H. W., Rosenheim O., Starling W. W. (1926) The chemical constitution of spermine. III.Structure and synthesis. Biochemical Journal 20(5): 1082-1094
- ^ Wrede F. (1925) Über die aus menschlichem Sperma isolierte Base Spermin. Dtsch. Med. Wochenschr. 51: 24
- ^ Klein, David (2013). Organic Chemistry (2nd ed.).
- ^ 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.
- ^ 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.
Further reading
- 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