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MedKoo Cat#: 555424 | Name: Spermine HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Spermine, a polycationic biogenic polyamine derived from spermidine, may be used in a wide variety of biological applications as a supplement or regulatory agent.Used as co-matrix with DHB for MALDI-MS of sialylated glycans in negative ion mode.

Chemical Structure

Spermine HCl
Spermine HCl
CAS#306-67-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 555424

Name: Spermine HCl

CAS#: 306-67-2 (HCl)

Chemical Formula: C10H30Cl4N4

Exact Mass: 0.0000

Molecular Weight: 348.18

Elemental Analysis: C, 34.50; H, 8.69; Cl, 40.73; N, 16.09

Price and Availability

Size Price Availability Quantity
1g USD 240.00 2 weeks
5g USD 500.00 2 weeks
25g USD 1,000.00 2 Weeks
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Related CAS #
71-44-3 (free base) 403982-64-9 (hydrate) 306-67-2 (HCl)
Synonym
Spermine HCl
IUPAC/Chemical Name
N,N′-Bis(3-aminopropyl)-1,4-butanediamine tetrahydrochloride
InChi Key
XLDKUDAXZWHPFH-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H26N4.4ClH/c11-5-3-9-13-7-1-2-8-14-10-4-6-12;;;;/h13-14H,1-12H2;4*1H
SMILES Code
NCCCNCCCCNCCCN.[H]Cl.[H]Cl.[H]Cl.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in water
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Spermine is an endogenous polyamine synthesized from the reaction of spermidine and is required for eukaryotic cell growth and protein synthesis.
In vitro activity:
Spermine could be a promising treatment for multiple sclerosis (MS). In vitro, spermine alleviated experimental autoimmune encephalomyelitis progression by inhibiting CD4+ T cells activation and T effector cell differentiation in a MAPK/ERK-dependent manner. Reference: Int Immunopharmacol. 2022 Jun;107:108702. https://pubmed.ncbi.nlm.nih.gov/35305382/
In vivo activity:
Spermine may have therapeutic potential in the treatment of diabetic cardiomyopathy-associated cardiac function deterioration. In a murine type II diabetic (T2D) model, there were 169 differentially expressed proteins in T2D mice compared to controls, and 16 proteins associated with various cellular and metabolic processes were differentially expressed in spermine-treated T2D mice compared to untreated T2D mice. Spermine treatment also affected the production of 51 metabolites. Reference: Front Cardiovasc Med. 2022 Oct 14;9:1022861. https://pubmed.ncbi.nlm.nih.gov/36312255/
Solvent mg/mL mM comments
Solubility
Water 50.0 143.60
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 348.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Zheng R, Kong M, Wang S, He B, Xie X. Spermine alleviates experimental autoimmune encephalomyelitis via regulating T cell activation and differentiation. Int Immunopharmacol. 2022 Jun;107:108702. doi: 10.1016/j.intimp.2022.108702. Epub 2022 Mar 16. PMID: 35305382. 2. Ha HC, Sirisoma NS, Kuppusamy P, Zweier JL, Woster PM, Casero RA Jr. The natural polyamine spermine functions directly as a free radical scavenger. Proc Natl Acad Sci U S A. 1998 Sep 15;95(19):11140-5. doi: 10.1073/pnas.95.19.11140. PMID: 9736703; PMCID: PMC21609. 3. Inamdar S, Tylek T, Thumsi A, Suresh AP, Jaggarapu MMCS, Halim M, Mantri S, Esrafili A, Ng ND, Schmitzer E, Lintecum K, de Ávila C, Fryer JD, Xu Y, Spiller KL, Acharya AP. Biomaterial mediated simultaneous delivery of spermine and alpha ketoglutarate modulate metabolism and innate immune cell phenotype in sepsis mouse models. Biomaterials. 2023 Feb;293:121973. doi: 10.1016/j.biomaterials.2022.121973. Epub 2022 Dec 17. PMID: 36549041; PMCID: PMC9868086. 4. Sun J, Xu J, Liu Y, Xu X, Zhang S, Hao Y, Lin Y, Han Y, Li F, Yuan H. Proteomic and metabolomic analyses reveal the novel targets of spermine for alleviating diabetic cardiomyopathy in type II diabetic mice. Front Cardiovasc Med. 2022 Oct 14;9:1022861. doi: 10.3389/fcvm.2022.1022861. PMID: 36312255; PMCID: PMC9614018.
In vitro protocol:
1. Zheng R, Kong M, Wang S, He B, Xie X. Spermine alleviates experimental autoimmune encephalomyelitis via regulating T cell activation and differentiation. Int Immunopharmacol. 2022 Jun;107:108702. doi: 10.1016/j.intimp.2022.108702. Epub 2022 Mar 16. PMID: 35305382. 2. Ha HC, Sirisoma NS, Kuppusamy P, Zweier JL, Woster PM, Casero RA Jr. The natural polyamine spermine functions directly as a free radical scavenger. Proc Natl Acad Sci U S A. 1998 Sep 15;95(19):11140-5. doi: 10.1073/pnas.95.19.11140. PMID: 9736703; PMCID: PMC21609.
In vivo protocol:
1. Inamdar S, Tylek T, Thumsi A, Suresh AP, Jaggarapu MMCS, Halim M, Mantri S, Esrafili A, Ng ND, Schmitzer E, Lintecum K, de Ávila C, Fryer JD, Xu Y, Spiller KL, Acharya AP. Biomaterial mediated simultaneous delivery of spermine and alpha ketoglutarate modulate metabolism and innate immune cell phenotype in sepsis mouse models. Biomaterials. 2023 Feb;293:121973. doi: 10.1016/j.biomaterials.2022.121973. Epub 2022 Dec 17. PMID: 36549041; PMCID: PMC9868086. 2. Sun J, Xu J, Liu Y, Xu X, Zhang S, Hao Y, Lin Y, Han Y, Li F, Yuan H. Proteomic and metabolomic analyses reveal the novel targets of spermine for alleviating diabetic cardiomyopathy in type II diabetic mice. Front Cardiovasc Med. 2022 Oct 14;9:1022861. doi: 10.3389/fcvm.2022.1022861. PMID: 36312255; PMCID: PMC9614018.
1: Cervelli M, Leonetti A, Duranti G, Sabatini S, Ceci R, Mariottini P. Skeletal Muscle Pathophysiology: The Emerging Role of Spermine Oxidase and Spermidine. Med Sci (Basel). 2018 Feb 14;6(1). pii: E14. doi: 10.3390/medsci6010014. Review. PubMed PMID: 29443878; PubMed Central PMCID: PMC5872171. 2: Sindhu KK. Uremic toxins: some thoughts on acrolein and spermine. Ren Fail. 2016 Nov;38(10):1755-1758. doi: 10.1080/0886022X.2016.1229990. Epub 2016 Oct 19. Review. PubMed PMID: 27758122. 3: Khomutov MA, Weisell J, Hyvönen M, Keinänen TA, Vepsäläinen J, Alhonen L, Khomutov AR, Kochetkov SN. Hydroxylamine derivatives for regulation of spermine and spermidine metabolism. Biochemistry (Mosc). 2013 Dec;78(13):1431-46. doi: 10.1134/S0006297913130051. Review. PubMed PMID: 24490733. 4: Pegg AE. The function of spermine. IUBMB Life. 2014 Jan;66(1):8-18. doi: 10.1002/iub.1237. Epub 2014 Jan 6. Review. PubMed PMID: 24395705. 5: Grancara S, Martinis P, Manente S, García-Argáez AN, Tempera G, Bragadin M, Dalla Via L, Agostinelli E, Toninello A. Bidirectional fluxes of spermine across the mitochondrial membrane. Amino Acids. 2014 Mar;46(3):671-9. doi: 10.1007/s00726-013-1591-0. Epub 2013 Sep 17. Review. PubMed PMID: 24043461. 6: Amendola R, Cervelli M, Tempera G, Fratini E, Varesio L, Mariottini P, Agostinelli E. Spermine metabolism and radiation-derived reactive oxygen species for future therapeutic implications in cancer: an additive or adaptive response. Amino Acids. 2014 Mar;46(3):487-98. doi: 10.1007/s00726-013-1579-9. Epub 2013 Sep 3. Review. PubMed PMID: 23999645. 7: Cervelli M, Salvi D, Polticelli F, Amendola R, Mariottini P. Structure-function relationships in the evolutionary framework of spermine oxidase. J Mol Evol. 2013 Jun;76(6):365-70. doi: 10.1007/s00239-013-9570-3. Epub 2013 Jul 5. Review. PubMed PMID: 23828398. 8: Alarcon RA. Anticancer system created by acrolein and hydroxyl radical generated in enzymatic oxidation of spermine and other biochemical reactions. Med Hypotheses. 2012 Oct;79(4):522-30. doi: 10.1016/j.mehy.2012.07.010. Epub 2012 Aug 6. Review. PubMed PMID: 22874453. 9: Chaturvedi R, de Sablet T, Peek RM, Wilson KT. Spermine oxidase, a polyamine catabolic enzyme that links Helicobacter pylori CagA and gastric cancer risk. Gut Microbes. 2012 Jan-Feb;3(1):48-56. doi: 10.4161/gmic.19345. Review. PubMed PMID: 22555547; PubMed Central PMCID: PMC3337125. 10: Cervelli M, Amendola R, Polticelli F, Mariottini P. Spermine oxidase: ten years after. Amino Acids. 2012 Feb;42(2-3):441-50. doi: 10.1007/s00726-011-1014-z. Epub 2011 Aug 2. Review. PubMed PMID: 21809080. 11: Mattoo AK, Minocha SC, Minocha R, Handa AK. Polyamines and cellular metabolism in plants: transgenic approaches reveal different responses to diamine putrescine versus higher polyamines spermidine and spermine. Amino Acids. 2010 Feb;38(2):405-13. doi: 10.1007/s00726-009-0399-4. Epub 2009 Dec 3. Review. PubMed PMID: 19956999. 12: Pegg AE, Michael AJ. Spermine synthase. Cell Mol Life Sci. 2010 Jan;67(1):113-21. doi: 10.1007/s00018-009-0165-5. Epub 2009 Oct 27. Review. PubMed PMID: 19859664; PubMed Central PMCID: PMC2822986. 13: Amendola R, Cervelli M, Fratini E, Polticelli F, Sallustio DE, Mariottini P. Spermine metabolism and anticancer therapy. Curr Cancer Drug Targets. 2009 Mar;9(2):118-30. Review. PubMed PMID: 19275753. 14: Pegg AE. Spermidine/spermine-N(1)-acetyltransferase: a key metabolic regulator. Am J Physiol Endocrinol Metab. 2008 Jun;294(6):E995-1010. doi: 10.1152/ajpendo.90217.2008. Epub 2008 Mar 18. Review. PubMed PMID: 18349109. 15: Agostinelli E, Seiler N. Lysosomotropic compounds and spermine enzymatic oxidation products in cancer therapy (review). Int J Oncol. 2007 Sep;31(3):473-84. Review. PubMed PMID: 17671672. 16: Kawakita M, Hiramatsu K. Diacetylated derivatives of spermine and spermidine as novel promising tumor markers. J Biochem. 2006 Mar;139(3):315-22. Review. PubMed PMID: 16567395. 17: Seiler N. How important is the oxidative degradation of spermine?: minireview article. Amino Acids. 2004 Jul;26(4):317-9. Epub 2004 Jun 11. Review. PubMed PMID: 15290336. 18: Stanfield PR, Sutcliffe MJ. Spermine is fit to block inward rectifier (Kir) channels. J Gen Physiol. 2003 Nov;122(5):481-4. Review. PubMed PMID: 14581580; PubMed Central PMCID: PMC2229586. 19: Bienz S, Detterbeck R, Ensch C, Guggisberg A, Häusermann U, Meisterhans C, Wendt B, Werner C, Hesse M. Putrescine, spermidine, spermine, and related polyamine alkaloids. Alkaloids Chem Biol. 2002;58:83-338. Review. PubMed PMID: 12534249. 20: Pellegrini-Giampietro DE. An activity-dependent spermine-mediated mechanism that modulates glutamate transmission. Trends Neurosci. 2003 Jan;26(1):9-11. Review. PubMed PMID: 12495855.