Spermine

Identification

Generic Name
Spermine
DrugBank Accession Number
DB00127
Background

Spermine is a spermidine-derived biogenic polyamine found as a polycation at all pH values. Found in various tissues and organisms, it often acts as an essential growth factor in some bacterial species. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure.

Type
Small Molecule
Groups
Experimental, Nutraceutical
Structure
Weight
Average: 202.3402
Monoisotopic: 202.215746852
Chemical Formula
C10H26N4
Synonyms
  • 4,9-diaza-1,12-dodecanediamine
  • 4,9-diazadodecane-1,12-diamine
  • Musculamine
  • N,N'-Bis(3-aminopropyl)-1,4-butanediamine
  • Spermina
  • Spermine
External IDs
  • NSC-268508

Pharmacology

Indication

For nutritional supplementation, also for treating dietary shortage or imbalance

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Pharmacodynamics

Spermine is a polyamine. It is an organic molecule that is involved in cellular metabolism.

Mechanism of action

Spermine is derived from spermidine by spermine synthase. Spermine is a polyamine, a small organic cations that is absolutely required for eukaryotic cell growth. Spermine, is normally found in millimolar concentrations in the nucleus. Spermine functions directly as a free radical scavenger, and forms a variety of adducts that prevent oxidative damage to DNA. Oxidative damage to DNA by reactive oxygen species is a continual problem that cells must guard against to survive. Hence, spermine is a major natural intracellular compound capable of protecting DNA from free radical attack. Spermine is also implicated in the regulation of gene expression, the stabilization of chromatin, and the prevention of endonuclease-mediated DNA fragmentation.

TargetActionsOrganism
ASpermine synthase
ligand
Humans
ASpermine oxidase
ligand
Humans
ADNA
binder
Humans
UOrnithine decarboxylase
product of
Humans
UExtracellular calcium-sensing receptorNot AvailableHumans
UBeta-1 adrenergic receptorNot AvailableHumans
UBeta-2 adrenergic receptorNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Spermidine and Spermine BiosynthesisMetabolic
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcyclovirThe risk or severity of adverse effects can be increased when Acyclovir is combined with Spermine.
AmantadineThe risk or severity of adverse effects can be increased when Amantadine is combined with Spermine.
ChlorpheniramineThe risk or severity of adverse effects can be increased when Chlorpheniramine is combined with Spermine.
CholineThe risk or severity of adverse effects can be increased when Choline is combined with Spermine.
Choline salicylateThe risk or severity of adverse effects can be increased when Choline salicylate is combined with Spermine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Spermine dihydrateNot Available403982-64-9MTNRSMVAYLLBAV-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Dialkylamines
Alternative Parents
Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Hydrocarbon derivative / Organopnictogen compound / Primary aliphatic amine / Primary amine / Secondary aliphatic amine
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
tetraamine, polyazaalkane (CHEBI:15746)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
2FZ7Y3VOQX
CAS number
71-44-3
InChI Key
PFNFFQXMRSDOHW-UHFFFAOYSA-N
InChI
InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2
IUPAC Name
(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine
SMILES
NCCCNCCCCNCCCN

References

Synthesis Reference

Koji Nakanishi, Amira T. Eldefrawi, Mohyee E. Eldefrawi, Peter N. R. Usherwood, "Butyryl-tyrosinyl spermine, analogs thereof and methods of preparing and using same." U.S. Patent US5770625, issued January, 1966.

US5770625
General References
Not Available
Human Metabolome Database
HMDB0001256
KEGG Compound
C00750
PubChem Compound
1103
PubChem Substance
46507215
ChemSpider
1072
BindingDB
79403
RxNav
1483263
ChEBI
15746
ChEMBL
CHEMBL23194
ZINC
ZINC000001532734
PharmGKB
PA164781199
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
SPM
Wikipedia
Spermine
PDB Entries
100d / 131d / 198d / 1d10 / 1d12 / 1d15 / 1d48 / 1dcr / 1dns / 1dpl
show 189 more
MSDS
Download (19.4 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
0CompletedPreventionNEC / Premature Births1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)29 °CPhysProp
boiling point (°C)150-150 °CNot Available
water solubility> 100 mg/mLNot Available
logP-0.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.19 mg/mLALOGPS
logP-0.66ALOGPS
logP-1.5Chemaxon
logS-2ALOGPS
pKa (Strongest Basic)10.8Chemaxon
Physiological Charge4Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area76.1 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity62.56 m3·mol-1Chemaxon
Polarizability26.69 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9215
Blood Brain Barrier+0.6345
Caco-2 permeable+0.7072
P-glycoprotein substrateNon-substrate0.5094
P-glycoprotein inhibitor INon-inhibitor0.9178
P-glycoprotein inhibitor IINon-inhibitor0.6414
Renal organic cation transporterNon-inhibitor0.6066
CYP450 2C9 substrateNon-substrate0.8863
CYP450 2D6 substrateNon-substrate0.5607
CYP450 3A4 substrateNon-substrate0.8262
CYP450 1A2 substrateInhibitor0.877
CYP450 2C9 inhibitorNon-inhibitor0.9072
CYP450 2D6 inhibitorNon-inhibitor0.9502
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9703
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9386
Ames testNon AMES toxic0.8957
CarcinogenicityNon-carcinogens0.6436
BiodegradationReady biodegradable0.5525
Rat acute toxicity2.4561 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7691
hERG inhibition (predictor II)Non-inhibitor0.7739
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.5 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)GC-MSsplash10-014u-1900000000-e9620319823eaecceccc
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (x TMS)GC-MSsplash10-00s6-3900000000-d7da5cd1c0be289412ee
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00r6-1900000000-861e0541e2eb67219b93
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)GC-MSsplash10-00di-7900000000-9706a16d903df3f9e094
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)GC-MSsplash10-00di-5900000000-eb1574dc4aea2972932b
GC-MS Spectrum - GC-MS (5 TMS)GC-MSsplash10-00ei-8900000000-710d44c573ed398f7db9
GC-MS Spectrum - GC-MS (5 TMS)GC-MSsplash10-00s6-3900000000-cb82c1371fa767015cff
GC-MS Spectrum - GC-MS (6 TMS)GC-MSsplash10-00rf-1900000000-ca3a2df44acb740134cd
GC-MS Spectrum - GC-MS (6 TMS)GC-MSsplash10-00y0-1900000000-7ba8e67861945901b381
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-053r-9300000000-2ce22d19e72f10b80f34
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014u-1900000000-e9620319823eaecceccc
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00s6-3900000000-d7da5cd1c0be289412ee
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00r6-1900000000-861e0541e2eb67219b93
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-7900000000-9706a16d903df3f9e094
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-5900000000-eb1574dc4aea2972932b
GC-MS Spectrum - GC-MSGC-MSsplash10-00ei-8900000000-710d44c573ed398f7db9
GC-MS Spectrum - GC-MSGC-MSsplash10-00s6-3900000000-cb82c1371fa767015cff
GC-MS Spectrum - GC-MSGC-MSsplash10-00rf-1900000000-ca3a2df44acb740134cd
GC-MS Spectrum - GC-MSGC-MSsplash10-00y0-1900000000-7ba8e67861945901b381
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-01bl-1900000000-5a4875c4cf337f0cff9c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-7900000000-4e66988ec8e890a03e13
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00rf-2900000000-9d5a63fbbd1662e5dc43
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-01w1-4900000000-f7c07f1cee7101fc31d7
Mass Spectrum (Electron Ionization)MSsplash10-053u-9100000000-5a106273203d28e4a701
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0w29-2940000000-a8b05c7cfaea58c5d82d
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-03di-1900000000-75ac3953e5378c465a62
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-001i-9000000000-e3b84db5723912be8a4f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0930000000-4bb02118dea11e2101f8
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-9000000000-468357ae06dea8985d85
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-00b9-6900000000-cf244bbfdbb5b7889d7a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-004i-0900000000-c5af077deeab934c36b7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0udi-0940000000-098121f449eb29dd74be
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0006-9000000000-167ef7503b0827eb212f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-03di-0900000000-feb04e188e675948f795
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-004i-0900000000-93e15f4592fe9bbeb367
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0udi-0090000000-c22e98adb3dc62b1eb77
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-01t9-0900000000-76aa5e4bf523c2027cba
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-03di-4900000000-b762c20d8a09a78cf931
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-001i-9300000000-0428cb6df2b593ded567
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-001i-9000000000-c319f927047d78e2b69b
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-004i-0900000000-b4f106f6fe26766fbf73
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-03di-0900000000-29d4a223bb44ded927b5
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-01q9-9500000000-d1b7e914e9ccee2d0f66
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a7r-0900000000-fac270438b8fcf4ab6e1
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a5i-0900000000-e37646be91d9c9ee86aa
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0569-0900000000-4d527955962f0242405e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ufr-0890000000-6c642f7409e64c7af826
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-1900000000-c54f5dadf66cbeb35a5f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01q9-9700000000-23a9dff5cfa7893bf88a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-9100000000-94edccd3f0c29b1d1550
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0090000000-c22e98adb3dc62b1eb77
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01t9-0900000000-76aa5e4bf523c2027cba
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-4900000000-b762c20d8a09a78cf931
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9300000000-0428cb6df2b593ded567
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-1df19a69c6a0bfd8952c
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-004i-0900000000-85dd13e7835fce38f035
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-468357ae06dea8985d85
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00b9-6900000000-cf244bbfdbb5b7889d7a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-c5af077deeab934c36b7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9000000000-167ef7503b0827eb212f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0900000000-feb04e188e675948f795
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-93e15f4592fe9bbeb367
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0ufr-0980000000-04ba3a80661fa28e4e84
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0ufr-0890000000-273c1447b41e06cc123c
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0ufr-0890000000-a520d943c6a95760eb51
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0900000000-09de27ed48a14b4412cf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-641a457dafd3f5d9d798
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0590000000-5756842e1e9673557329
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-ccfb30322bb4349aecbe
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-3900000000-490d1327c68e4b7e7ae2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-007c-9100000000-bc80c0905fd5628717a1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a59-9200000000-94e6e36555021db62642
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.0870987
predicted
DarkChem Lite v0.1.0
[M-H]-157.2835987
predicted
DarkChem Lite v0.1.0
[M-H]-145.28842
predicted
DeepCCS 1.0 (2019)
[M+H]+157.5024987
predicted
DarkChem Lite v0.1.0
[M+H]+156.9285987
predicted
DarkChem Lite v0.1.0
[M+H]+148.63876
predicted
DeepCCS 1.0 (2019)
[M+Na]+157.2674987
predicted
DarkChem Lite v0.1.0
[M+Na]+157.6892987
predicted
DarkChem Lite v0.1.0
[M+Na]+158.01805
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Ligand
General Function
Spermine synthase activity
Specific Function
Catalyzes the production of spermine from spermidine and decarboxylated S-adenosylmethionine (dcSAM).
Gene Name
SMS
Uniprot ID
P52788
Uniprot Name
Spermine synthase
Molecular Weight
41267.855 Da
References
  1. Lopatin AN, Shantz LM, Mackintosh CA, Nichols CG, Pegg AE: Modulation of potassium channels in the hearts of transgenic and mutant mice with altered polyamine biosynthesis. J Mol Cell Cardiol. 2000 Nov;32(11):2007-24. [Article]
  2. Korhonen VP, Niiranen K, Halmekyto M, Pietila M, Diegelman P, Parkkinen JJ, Eloranta T, Porter CW, Alhonen L, Janne J: Spermine deficiency resulting from targeted disruption of the spermine synthase gene in embryonic stem cells leads to enhanced sensitivity to antiproliferative drugs. Mol Pharmacol. 2001 Feb;59(2):231-8. [Article]
  3. Cason AL, Ikeguchi Y, Skinner C, Wood TC, Holden KR, Lubs HA, Martinez F, Simensen RJ, Stevenson RE, Pegg AE, Schwartz CE: X-linked spermine synthase gene (SMS) defect: the first polyamine deficiency syndrome. Eur J Hum Genet. 2003 Dec;11(12):937-44. [Article]
  4. Wang X, Ikeguchi Y, McCloskey DE, Nelson P, Pegg AE: Spermine synthesis is required for normal viability, growth, and fertility in the mouse. J Biol Chem. 2004 Dec 3;279(49):51370-5. Epub 2004 Sep 30. [Article]
  5. Schwartz CE, Wang X, Stevenson RE, Pegg AE: Spermine synthase deficiency resulting in X-linked intellectual disability (Snyder-Robinson syndrome). Methods Mol Biol. 2011;720:437-45. doi: 10.1007/978-1-61779-034-8_28. [Article]
  6. Wang X, Pegg AE: Use of (Gyro) Gy and spermine synthase transgenic mice to study functions of spermine. Methods Mol Biol. 2011;720:159-70. doi: 10.1007/978-1-61779-034-8_9. [Article]
  7. Theiss C, Bohley P, Voigt J: Regulation by polyamines of ornithine decarboxylase activity and cell division in the unicellular green alga Chlamydomonas reinhardtii. Plant Physiol. 2002 Apr;128(4):1470-9. [Article]
  8. Krauss M, Langnaese K, Richter K, Brunk I, Wieske M, Ahnert-Hilger G, Veh RW, Laube G: Spermidine synthase is prominently expressed in the striatal patch compartment and in putative interneurones of the matrix compartment. J Neurochem. 2006 Apr;97(1):174-89. Epub 2006 Mar 3. [Article]
  9. Kobayashi M, Takao K, Shiota Y, Sugita Y, Takahashi M, Nakae D, Samejima K: Inhibition of putrescine aminopropyltransferase influences rat liver regeneration. Biol Pharm Bull. 2006 May;29(5):863-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Ligand
General Function
Spermine:oxygen oxidoreductase (spermidine-forming) activity
Specific Function
Flavoenzyme which catalyzes the oxidation of spermine to spermidine. Can also use N(1)-acetylspermine and spermidine as substrates, with different affinity depending on the isoform (isozyme) and on...
Gene Name
SMOX
Uniprot ID
Q9NWM0
Uniprot Name
Spermine oxidase
Molecular Weight
61818.76 Da
References
  1. Binda C, Angelini R, Federico R, Ascenzi P, Mattevi A: Structural bases for inhibitor binding and catalysis in polyamine oxidase. Biochemistry. 2001 Mar 6;40(9):2766-76. [Article]
  2. Vujcic S, Diegelman P, Bacchi CJ, Kramer DL, Porter CW: Identification and characterization of a novel flavin-containing spermine oxidase of mammalian cell origin. Biochem J. 2002 Nov 1;367(Pt 3):665-75. [Article]
  3. Vujcic S, Liang P, Diegelman P, Kramer DL, Porter CW: Genomic identification and biochemical characterization of the mammalian polyamine oxidase involved in polyamine back-conversion. Biochem J. 2003 Feb 15;370(Pt 1):19-28. [Article]
  4. Wang Y, Murray-Stewart T, Devereux W, Hacker A, Frydman B, Woster PM, Casero RA Jr: Properties of purified recombinant human polyamine oxidase, PAOh1/SMO. Biochem Biophys Res Commun. 2003 May 16;304(4):605-11. [Article]
  5. Bacchi CJ, Rattendi D, Faciane E, Yarlett N, Weiss LM, Frydman B, Woster P, Wei B, Marton LJ, Wittner M: Polyamine metabolism in a member of the phylum Microspora (Encephalitozoon cuniculi): effects of polyamine analogues. Microbiology. 2004 May;150(Pt 5):1215-24. [Article]
Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Binder
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Trubetskoy VS, Wolff JA, Budker VG: The role of a microscopic colloidally stabilized phase in solubilizing oligoamine-condensed DNA complexes. Biophys J. 2003 Feb;84(2 Pt 1):1124-30. [Article]
  2. Cho SK, Kwon YJ: Polyamine/DNA polyplexes with acid-degradable polymeric shell as structurally and functionally virus-mimicking nonviral vectors. J Control Release. 2011 Mar 30;150(3):287-97. doi: 10.1016/j.jconrel.2010.12.004. Epub 2010 Dec 16. [Article]
  3. Saminathan M, Thomas T, Shirahata A, Pillai CK, Thomas TJ: Polyamine structural effects on the induction and stabilization of liquid crystalline DNA: potential applications to DNA packaging, gene therapy and polyamine therapeutics. Nucleic Acids Res. 2002 Sep 1;30(17):3722-31. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Product of
General Function
Protein homodimerization activity
Specific Function
Key enzyme of polyamine biosynthesis that converts ornithine into putrescine, which is the precursor for the polyamines, spermidine and spermine.
Gene Name
ODC1
Uniprot ID
P11926
Uniprot Name
Ornithine decarboxylase
Molecular Weight
51147.73 Da
References
  1. Nilsson J, Grahn B, Heby O: Antizyme inhibitor is rapidly induced in growth-stimulated mouse fibroblasts and releases ornithine decarboxylase from antizyme suppression. Biochem J. 2000 Mar 15;346 Pt 3:699-704. [Article]
  2. Ray RM, Viar MJ, Yuan Q, Johnson LR: Polyamine depletion delays apoptosis of rat intestinal epithelial cells. Am J Physiol Cell Physiol. 2000 Mar;278(3):C480-9. [Article]
  3. Korhonen VP, Niiranen K, Halmekyto M, Pietila M, Diegelman P, Parkkinen JJ, Eloranta T, Porter CW, Alhonen L, Janne J: Spermine deficiency resulting from targeted disruption of the spermine synthase gene in embryonic stem cells leads to enhanced sensitivity to antiproliferative drugs. Mol Pharmacol. 2001 Feb;59(2):231-8. [Article]
  4. Rohn G, Els T, Hell K, Ernestus RI: Regional distribution of ornithine decarboxylase activity and polyamine levels in experimental cat brain tumors. Neurochem Int. 2001 Aug;39(2):135-40. [Article]
  5. Ernestus RI, Rohn G, Schroder R, Els T, Klekner A, Paschen W, Klug N: Polyamine metabolism in brain tumours: diagnostic relevance of quantitative biochemistry. J Neurol Neurosurg Psychiatry. 2001 Jul;71(1):88-92. [Article]
  6. Lee NK, MacLean HE: Polyamines, androgens, and skeletal muscle hypertrophy. J Cell Physiol. 2011 Jun;226(6):1453-60. doi: 10.1002/jcp.22569. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
Senses changes in the extracellular concentration of calcium ions. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol-calcium second messenger system.
Gene Name
CASR
Uniprot ID
P41180
Uniprot Name
Extracellular calcium-sensing receptor
Molecular Weight
120672.385 Da
References
  1. El Hiani Y, Ahidouch A, Roudbaraki M, Guenin S, Brule G, Ouadid-Ahidouch H: Calcium-sensing receptor stimulation induces nonselective cation channel activation in breast cancer cells. J Membr Biol. 2006;211(2):127-37. Epub 2006 Oct 14. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Meana C, Bordallo J, Bordallo C, Suarez L, Cantabrana B, Sanchez M: Functional effects of polyamines via activation of human beta1- and beta2-adrenoceptors stably expressed in CHO cells. Pharmacol Rep. 2010 Jul-Aug;62(4):696-706. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Meana C, Bordallo J, Bordallo C, Suarez L, Cantabrana B, Sanchez M: Functional effects of polyamines via activation of human beta1- and beta2-adrenoceptors stably expressed in CHO cells. Pharmacol Rep. 2010 Jul-Aug;62(4):696-706. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Diamine n-acetyltransferase activity
Specific Function
Enzyme which catalyzes the acetylation of polyamines. Substrate specificity: norspermidine = spermidine >> spermine > N(1)-acetylspermine > putrescine. This highly regulated enzyme allows a fine at...
Gene Name
SAT1
Uniprot ID
P21673
Uniprot Name
Diamine acetyltransferase 1
Molecular Weight
20023.8 Da
References
  1. Vujcic S, Halmekyto M, Diegelman P, Gan G, Kramer DL, Janne J, Porter CW: Effects of conditional overexpression of spermidine/spermine N1-acetyltransferase on polyamine pool dynamics, cell growth, and sensitivity to polyamine analogs. J Biol Chem. 2000 Dec 8;275(49):38319-28. [Article]
  2. Hegardt C, Andersson G, Oredsson SM: Changes in polyamine metabolism during glucocorticoid-induced programmed cell death in mouse thymus. Cell Biol Int. 2000;24(12):871-80. [Article]
  3. Marverti G, Bettuzzi S, Astancolle S, Pinna C, Monti MG, Moruzzi MS: Differential induction of spermidine/spermine N1-acetyltransferase activity in cisplatin-sensitive and -resistant ovarian cancer cells in response to N1,N12-bis(ethyl)spermine involves transcriptional and post-transcriptional regulation. Eur J Cancer. 2001 Jan;37(2):281-9. [Article]
  4. Scorcioni F, Corti A, Davalli P, Astancolle S, Bettuzzi S: Manipulation of the expression of regulatory genes of polyamine metabolism results in specific alterations of the cell-cycle progression. Biochem J. 2001 Feb 15;354(Pt 1):217-23. [Article]
  5. Min SH, Simmen RC, Alhonen L, Halmekyto M, Porter CW, Janne J, Simmen FA: Altered levels of growth-related and novel gene transcripts in reproductive and other tissues of female mice overexpressing spermidine/spermine N1-acetyltransferase (SSAT). J Biol Chem. 2002 Feb 1;277(5):3647-57. Epub 2001 Nov 14. [Article]
  6. Limsuwun K, Jones PG: Spermidine acetyltransferase is required to prevent spermidine toxicity at low temperatures in Escherichia coli. J Bacteriol. 2000 Oct;182(19):5373-80. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Diamine n-acetyltransferase activity
Specific Function
Enzyme which catalyzes the acetylation of polyamines. Substrate specificity: norspermidine > spermidine = spermine >> N(1)acetylspermine = putrescine.
Gene Name
SAT2
Uniprot ID
Q96F10
Uniprot Name
Diamine acetyltransferase 2
Molecular Weight
19154.905 Da
References
  1. Chen Y, Vujcic S, Liang P, Diegelman P, Kramer DL, Porter CW: Genomic identification and biochemical characterization of a second spermidine/spermine N1-acetyltransferase. Biochem J. 2003 Aug 1;373(Pt 3):661-7. [Article]
  2. Coleman CS, Stanley BA, Jones AD, Pegg AE: Spermidine/spermine-N1-acetyltransferase-2 (SSAT2) acetylates thialysine and is not involved in polyamine metabolism. Biochem J. 2004 Nov 15;384(Pt 1):139-48. [Article]
  3. Vogel NL, Boeke M, Ashburner BP: Spermidine/Spermine N1-Acetyltransferase 2 (SSAT2) functions as a coactivator for NF-kappaB and cooperates with CBP and P/CAF to enhance NF-kappaB-dependent transcription. Biochim Biophys Acta. 2006 Oct;1759(10):470-7. Epub 2006 Aug 30. [Article]
  4. Limsuwun K, Jones PG: Spermidine acetyltransferase is required to prevent spermidine toxicity at low temperatures in Escherichia coli. J Bacteriol. 2000 Oct;182(19):5373-80. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xanthine oxidase activity
Specific Function
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Ha...
Gene Name
XDH
Uniprot ID
P47989
Uniprot Name
Xanthine dehydrogenase/oxidase
Molecular Weight
146422.99 Da
References
  1. Lovaas E, Carlin G: Spermine: an anti-oxidant and anti-inflammatory agent. Free Radic Biol Med. 1991;11(5):455-61. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Busch AE, Quester S, Ulzheimer JC, Waldegger S, Gorboulev V, Arndt P, Lang F, Koepsell H: Electrogenic properties and substrate specificity of the polyspecific rat cation transporter rOCT1. J Biol Chem. 1996 Dec 20;271(51):32599-604. [Article]
  2. Li DC, Nichols CG, Sala-Rabanal M: Role of a Hydrophobic Pocket in Polyamine Interactions with the Polyspecific Organic Cation Transporter OCT3. J Biol Chem. 2015 Nov 13;290(46):27633-43. doi: 10.1074/jbc.M115.668913. Epub 2015 Sep 24. [Article]

Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:42