Identification

Name
Spermine
Accession Number
DB00127  (NUTR00055, EXPT02947, DB02564)
Type
Small Molecule
Groups
Approved, Nutraceutical
Description

A biogenic polyamine formed from spermidine. 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 all pH values. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure. [PubChem]

Structure
Thumb
Synonyms
  • 4,9-Diaza-1,12-dodecanediamine
  • 4,9-Diazadodecane-1,12-diamine
  • N,N'-Bis(3-aminopropyl)-1,4-butanediamine
  • Spermine
External IDs
NSC-268508
Product Ingredients
IngredientUNIICASInChI Key
Spermine dihydrateNot AvailableNot AvailableNot applicable
Categories
UNII
2FZ7Y3VOQX
CAS number
71-44-3
Weight
Average: 202.3402
Monoisotopic: 202.215746852
Chemical Formula
C10H26N4
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

Pharmacology

Indication

For nutritional supplementation, also for treating dietary shortage or imbalance

Structured Indications
Not Available
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
Human
ASpermine oxidase
ligand
Human
ADNA
binder
Human
UOrnithine decarboxylase
product of
Human
UExtracellular calcium-sensing receptorNot AvailableHuman
UBeta-1 adrenergic receptorNot AvailableHuman
UBeta-2 adrenergic receptorNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Spermidine and Spermine BiosynthesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
External Links
Human Metabolome Database
HMDB01256
KEGG Compound
C00750
PubChem Compound
1103
PubChem Substance
46507215
ChemSpider
1072
BindingDB
79403
ChEBI
15746
ChEMBL
CHEMBL23194
PharmGKB
PA164781199
IUPHAR
710
Guide to Pharmacology
GtP Drug Page
HET
SPM
Wikipedia
Spermine
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
100d / 131d / 198d / 1d10 / 1d12 / 1d15 / 1d48 / 1dcr / 1dns / 1dpl
show 100 more
FDA label
Not Available
MSDS
Download (19.4 KB)

Clinical Trials

Clinical Trials
Not Available

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)11.1ChemAxon
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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-2970000000-268b93360fb5eaa19e49
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a73-9810000000-ee919f22493191f56708
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9200000000-f7cb18a7a6036554cb6b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-ea2e2f233958fa61cd8b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-3390000000-0ade7d389047531a84ee
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fu-9200000000-e760ec8b3259e54992ce
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
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Secondary aliphatic amine / Organopnictogen compound / Hydrocarbon derivative / Primary amine / Primary aliphatic amine / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
tetraamine, polyazaalkane (CHEBI:15746)

Targets

Kind
Protein
Organism
Human
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. [PubMed:11040105]
  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. [PubMed:11160858]
  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. [PubMed:14508504]
  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. [PubMed:15459188]
  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. [PubMed:21318891]
  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. [PubMed:21318872]
  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. [PubMed:11950995]
  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. [PubMed:16515550]
  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. [PubMed:16651710]
Kind
Protein
Organism
Human
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. [PubMed:11258887]
  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. [PubMed:12141946]
  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. [PubMed:12477380]
  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. [PubMed:12727196]
  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. [PubMed:15133083]
3. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Yes
Actions
Binder
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
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. [PubMed:12547793]
  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. [PubMed:21167887]
  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. [PubMed:12202757]
Kind
Protein
Organism
Human
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. [PubMed:10698696]
  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. [PubMed:10712236]
  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. [PubMed:11160858]
  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. [PubMed:11408092]
  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. [PubMed:11413269]
  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. [PubMed:21413019]
Kind
Protein
Organism
Human
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. [PubMed:17041782]
Kind
Protein
Organism
Human
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. [PubMed:20885010]
Kind
Protein
Organism
Human
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. [PubMed:20885010]

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:1663062]
Kind
Protein
Organism
Human
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. [PubMed:10978316]
  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. [PubMed:11114236]
  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. [PubMed:11166157]
  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. [PubMed:11171097]
  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. [PubMed:11709547]
  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. [PubMed:10986239]
Kind
Protein
Organism
Human
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. [PubMed:12803540]
  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. [PubMed:15283699]
  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. [PubMed:17011643]
  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. [PubMed:10986239]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:10215651]
Kind
Protein
Organism
Human
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. [PubMed:8955087]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:31