Spermine tetrahydrochloride for molecular biology

Product No. S1141

CAS RN 306-67-2
EC 206-189-8
Synonyms: N, N’-Bis(3-aminopropyl)-1,4-butanediamine tetrahydrochloride

Product Description

This product is suitable for DNA precipitation from low salt aqueous buffers. It has been tested for the absence of proteases and nucleases.

Spermine is a naturally occuring polyamine that occurs in all eukaryotes, but is rare in prokaryotes. It is essential for cell growth in both normal and neoplastic tissue.² Spermine is formed through the addition of a aminopropyl group to spermidine by spermine synthase. Spermine is strongly basic in character, and in aqueous solution at physiological pH, all of its amino groups will be positively charged.³ A review of the role of spermine and other polyamines in affecting RNA structure and protein function has been published.⁴

Spermine is commonly used in molecular biology and biochemistry research. The polycationic character of spermine in solution allows for its use in the precipitation of DNA of >100 base pairs in length from low salt aqueous buffers, and for the isolation of DNA from pulse field gels.^5,6,7 Spermine has also been utilized in chromosome isolation and in the aggregation of chromatin.^8,9 It may be used as a building block for the preparation of gene transfer agents.^10,11 The complexation of spermine with DNA to form particles with diameter <100 nm has been studied.¹² Spermine has been used in the crystallization of DNA.^13,14

It has been reported that spermine interacts with the glycine binding site associated with the N-methyl D-aspartate receptor complex.¹⁵ Spermine has been shown to inhibit the conversion of L-arginine to L-citrulline by neuronal nitric oxide synthase in cytosolic preparations of rat cerebellum and cultured cerebellar granule neurons.¹⁶ In acute hippocampal slices, 1 mM spermine exerts a neuroprotective effect by blocking the NMDA receptor and voltage-activated Ca²⁺ channels.¹⁷ The effect of spermine on MK-801 binding to recombinant N-methyl-D-aspartate receptors has been investigated.¹⁸ Proteins and protein complexes have been crystallized using spermine.^18,19 Other applications of spermine include its use as a matrix in MALDI-MS for analysis of glycoconjugates and oligonucleotides.^19,20

Precautions and Disclaimer

This product is for R&D use only, not for drug, household, or other uses. Please consult the Safety Data Sheet for information regarding hazards and safe handling practices.

Preparation Instructions

This product is soluble in water (100 mg/mL), yielding a clear, colorless to light yellow solution.

Storage/Stability

Solutions of spermine free base are readily oxidized.

Solutions are most stable if prepared in degassed water and stored in frozen aliquots, under argon or nitrogen gas.

Product Profile

Molecular Formula: C₁₀H₂₆N₄ · 4HCl
Molecular Weight: 348.18
Melting Point: 312 - 314.5 °C²¹

References

1. Morgan, D. M. L.. Methods in Molecular Biology, , ed., Humana Press (Totowa, NJ: 1998), pp. 3-30.. Volume 79: Polyamine Protocols

2. Igarashi K, Kashiwagi K. 2000. Polyamines: Mysterious Modulators of Cellular Functions. Biochemical and Biophysical Research Communications. 271(3):559-564. https://doi.org/10.1006/bbrc.2000.2601

3. Davis, et al. LG. , Appleton & Lang (Norwalk, CT: 1994).. Basic Methods in Molecular Biology, 2nd ed.,.

4. Wallace DM. 1987. [5] Precipitation of nucleic acids.41-48. https://doi.org/10.1016/0076-6879(87)52008-0

5. Sambrook J, Russell DW. Molecular Cloning: A Laboratory Manual, 3rd ed., CSHL Press (Cold Spring Harbor, NY: 2001), ..pp. .5.86-5.88.

6. Cram LS, Campbell M, Fawcett JJ, Deaven LL. 1990. Chapter 36 Polyamine Buffer for Bivariate Human Flow Cytogenetic Analysis and Sorting.377-382. https://doi.org/10.1016/s0091-679x(08)60541-5

7. Marquet, et al. R. The condensation of chromatin and histone H1-depleted chromatin by spermine..

8. Ronsin G, Perrin C, Guédat P, Kremer A, Camilleri P, Kirby AJ. 2001. Novel spermine-based cationic gemini surfactants for gene delivery. Chem. Commun..(21):2234. https://doi.org/10.1039/b105936j

9. Azzam T, Eliyahu H, Shapira L, Linial M, Barenholz Y, Domb AJ. 2002. Polysaccharide?Oligoamine Based Conjugates for Gene Delivery. J. Med. Chem.. 45(9):1817-1824. https://doi.org/10.1021/jm0105528

10. Trubetskoy VS, Wolff JA, Budker VG. 2003. The Role of a Microscopic Colloidally Stabilized Phase in Solubilizing Oligoamine-Condensed DNA Complexes. Biophysical Journal. 84(2):1124-1130. https://doi.org/10.1016/s0006-3495(03)74928-5

11. Shui X, McFail-Isom L, Hu GG, Williams LD. 1998. The B-DNA Dodecamer at High Resolution Reveals a Spine of Water on Sodium?,?. Biochemistry. 37(23):8341-8355. https://doi.org/10.1021/bi973073c

12. Sacaan AI, Johnson KM. Spermine enhances binding to the glycine site associated with the N-methyl-D-aspartate receptor complex. Mol. Pharmacol., 36(6), 836-839 (1989)..

13. Hu J, Mahmoud MI, El-Fakahany EE. 1994. Polyamines inhibit nitric oxide synthase in rat cerebellum. Neuroscience Letters. 175(1-2):41-45. https://doi.org/10.1016/0304-3940(94)91073-1

14. Ferchmin P, Pérez D, Biello M. 2000. Spermine is neuroprotective against anoxia and N-methyl-d-aspartate in hippocampal slices. Brain Research. 859(2):273-279. https://doi.org/10.1016/s0006-8993(00)01973-9

15. Sharma TA, Reynolds IJ. Characterization of the effects of polyamines on [125I]MK-801 binding to recombinant N-methyl D-aspartate receptors. J. Pharmacol. Exp. Ther., 289(2), 1041-1047 (1999)..

16. Xie X, Rao S, Walian P, Hatch V, Phillips GN, Cohen C. 1994. Coiled-coil packing in spermine-induced tropomyosin crystals a comparative study of three forms. Journal of Molecular Biology. 236(4):1212-1226. https://doi.org/10.1016/0022-2836(94)90022-1

17. Qian C, Lagacé L, Massariol M, Chabot C, Yoakim C, Déziel R, Tong L. 2000. A rational approach towards successful crystallization and crystal treatment of human cytomegalovirus protease and its inhibitor complex. Acta Crystallogr D Biol Cryst. 56(2):175-180. https://doi.org/10.1107/s0907444999015103

18. Mechref Y, Novotny MV. 1998. Matrix-assisted laser desorption/ionization mass spectrometry of acidic glycoconjugates facilitated by the use of spermine as a co-matrix. J Am Soc Mass Spectrom. 9(12):1293-1302. https://doi.org/10.1016/s1044-0305(98)00106-8

19. Asara JM, Allison J. 1999. Enhanced Detection of Oligonucleotides in UV MALDI MS Using the Tetraamine Spermine as a Matrix Additive. Anal. Chem.. 71(14):2866-2870. https://doi.org/10.1021/ac981406l

20. Greenstein GR. 2007. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14th edition)2007287Edited by Maryadele J. O'Neil. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14th edition). Whitehouse Station, NJ: Merck & Co. 2006. , ISBN: 978 0 911910 00 1 $125 £59.99 Includes a CD?ROM; distributed in the UK by John Wiley. Reference Reviews. 21(6):40-40. https://doi.org/10.1108/09504120710775534