| Revision as of 21:48, 7 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit |
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{{Short description| Polyamine involved in cellular metabolism}} |
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{{Redirect|BESm||BESM (disambiguation)}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 412139417 |
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| verifiedrevid = 459523063 |
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|ImageFile=Spermine.svg |
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| ImageFile = Spermine.svg |
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|ImageSize=300px |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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|ImageFileL2=Spermine_spacefill.png |
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| ImageName = Skeletal formula of spermine |
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|ImageSizeL2=150px |
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|ImageFileR2=Spermine2.png |
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| ImageFile1 = Spermine2.png |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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|ImageSizeR2=150px |
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| ImageName1 = Ball and stick model of spermine |
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|IUPACName=N,N'-bis(3-aminopropyl)butane-1,4-diamine |
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| ImageFile2 = Spermine_spacefill.png |
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|OtherNames=Gerontine<br/>Musculamine<br/>Neuridine |
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| ImageFile2_Ref = {{chemboximage|correct|??}} |
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|Section1= {{Chembox Identifiers |
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| ImageName2 = Spacefill model of spermine |
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| CASNo=71-44-3 |
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| PIN = ''N''<sup>1</sup>,''N''<sup>4</sup>-Bis(3-aminopropyl)butane-1,4-diamine |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|Section1={{Chembox Identifiers |
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| PubChem=1103 |
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| CASNo = 71-44-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Comment = (free base) |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASNo2 = 306-67-2 |
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| CASNo2_Comment = (tetrahydrochloride) <!--also verified against the Chemical Abstracts Service list --> |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 2FZ7Y3VOQX |
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| UNII_Comment = (free base) |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = 9CI1570O48 |
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| UNII2_Comment = (tetrahydrochloride) |
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| PubChem = 1103 |
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| ChemSpiderID = 1072 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| EINECS = 200-754-2 |
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| UNNumber = 3259 |
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| DrugBank = DB00127 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| KEGG = C00750 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| MeSHName = Spermine |
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| ChEBI = 15746 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 23194 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 23194 --> |
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| IUPHAR_ligand = 710 |
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| IUPHAR_ligand = 710 |
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| RTECS = EJ7175000 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = DB00127 |
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| Beilstein = 1750791 |
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| Gmelin = 454653 |
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| SMILES=C(CCNCCCN)CNCCCN |
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| 3DMet = B01325 |
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| MeSHName=Spermine |
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| SMILES = NCCCNCCCCNCCCN |
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}} |
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| StdInChI = 1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2 |
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|Section2= {{Chembox Properties |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| Formula=C<sub>10</sub>H<sub>26</sub>N<sub>4</sub> |
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| StdInChIKey = PFNFFQXMRSDOHW-UHFFFAOYSA-N |
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| MolarMass=202.34 g/mol |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| Appearance= |
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}} |
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| Density=0.937 g/cm<sup>3</sup> |
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|Section2={{Chembox Properties |
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| MeltingPt=29 °C |
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| C=10 | N=4 | H=26 |
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| BoilingPt=130 °C |
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| Appearance = Colourless crystals |
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| Solubility= |
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| Odor = Fishy or like that of semen |
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}} |
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| Density = 917 mg mL<sup>−1</sup> |
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|Section3= {{Chembox Hazards |
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| MeltingPtC = 28 to 30 |
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| MainHazards= |
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| BoilingPtK = 423.2 |
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| FlashPt= |
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| BoilingPt_notes = at 700 Pa |
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| Autoignition= |
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| LogP = −0.543 |
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}} |
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|Section3={{Chembox Hazards |
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| GHSPictograms = {{gHS corrosion}} |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{h-phrases|314}} |
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| PPhrases = {{p-phrases|280|305+351+338|310}} |
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| FlashPtC = 110 |
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| MainHazards = corrosive |
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}} |
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|Section4={{Chembox Related |
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| OtherCompounds = ], ], ], ], ], ] |
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}} |
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'''Spermine''' is a ] involved in ] found in all ]. Formed from ], it is found in a wide variety of organisms and tissues and is an essential ] in some ]. It is found as a polycation at physiological pH. Spermine is associated with ]s and is thought to stabilize helical structure, in particular, in ]es. |
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'''Spermine''' is a ] involved in ] that is found in all ]. The precursor for synthesis of spermine is the amino acid ]. It is an essential ] in some ] as well. It is found as a ] at physiological pH. Spermine is associated with ]s and is thought to stabilize helical structure, particularly in ]es. It functions as an intracellular ] to protect DNA from free radical attack.<ref name="Ha 1998">{{cite journal | last1=Ha | first1=Hyo Chol | last2=Sirisoma | first2=Nilantha S. | last3=Kuppusamy | first3=Periannan | last4=Zweier | first4=Jay L. | last5=Woster | first5=Patrick M. | last6=Casero | first6=Robert A. | title=The natural polyamine spermine functions directly as a free radical scavenger | journal=PNAS | volume=95 | issue=19 | date=1998-09-15 | pages=11140–11145 | issn=0027-8424 | doi=10.1073/pnas.95.19.11140 | doi-access=free | pmid=9736703 | pmc=21609 }}</ref> Spermine is the chemical primarily responsible for the characteristic odor of semen.<ref> |
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Crystals of spermine phosphate were first described in 1678, in human ], by ]<ref>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.</ref>. The name ''spermin'' was first used by the German chemists ] and Abel in 1888<ref>Ladenburg A., Abel J. (1888) Über das Aethylenimin (Spermin?). ''Ber. Dtsch. chem. Ges.'' 21: 758-766</ref>, and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling)<ref></ref> and Germany (by Wrede et al.)<ref>Wrede F. (1925) Über die aus menschlichem Sperma isolierte Base Spermin. ''Dtsch. Med. Wochenschr.'' 51: 24</ref>. |
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{{Cite book | author = Klein, David | date = 2013 | title = Organic Chemistry | edition = 2nd }} |
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</ref> |
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] first described crystals of spermine ] in human ] in 1678.<ref>{{cite journal | doi = 10.1098/rstl.1677.0068 | title = Observationes D. Anthonii Lewenhoeck, De Natis E Semine Genitali Animalculis | journal = Philosophical Transactions of the Royal Society of London | volume = 12 | issue = 133–142 | pages = 1040–1046 | year = 1677 | last1 = Lewenhoeck | first1 = D. A | bibcode = 1677RSPT...12.1040A | url = https://zenodo.org/record/1432128 | doi-access = free }}</ref> The name ''spermin'' was first used by the German chemists ] and Abel in 1888,<ref>{{cite journal | doi = 10.1002/cber.188802101139| title = Ueber das Aethylenimin (Spermin?)| journal = Berichte der Deutschen Chemischen Gesellschaft| volume = 21| pages = 758–766| year = 1888| last1 = Ladenburg| first1 = A| last2 = Abel| first2 = J| url = https://zenodo.org/record/1425507}}</ref><ref>{{cite journal | doi = 10.1002/cber.18880210293 | title = Nachtrag zu der Mittheilung über das Aethylenimin | journal = Berichte der Deutschen Chemischen Gesellschaft| volume = 21| issue = 2| pages = 2706| year =1888| last1 =Ladenburg| first1 =A| last2 =Abel| first2 =J| url = https://zenodo.org/record/1425549}}</ref> and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling)<ref>{{cite journal | pmc = 1251823 |year = 1926|last1 = Dudley|first1 = H. W|title = The Chemical Constitution of Spermine: Structure and Synthesis|journal = Biochemical Journal|volume = 20|issue = 5|pages = 1082–1094|last2 = Rosenheim|first2 = O|last3 = Starling |first3 = W. W|pmid= 16743746|doi= 10.1042/bj0201082}}</ref><ref>{{cite journal | doi = 10.1042/bj0181263| pmid =16743399| title =The Chemical Constitution of Spermine. I. The Isolation of Spermine from Animal Tissues, and the Preparation of its Salts| journal = Biochemical Journal| volume = 18| issue = 6| pages = 1263–72| year = 1924| last1 = Dudley| first1 =Harold Ward| last2 =Rosenheim| first2 =Mary Christine| last3 =Rosenheim| first3 = Otto| pmc=1259516}}</ref> and Germany (by Wrede et al.).<ref>{{cite journal | doi = 10.1055/s-0028-1136345 | title =Ueber die aus dem menschlichen Sperma isolierte Base Spermin | journal =Deutsche Medizinische Wochenschrift| volume =51| pages =24| year =2009| last1 = Wrede| first1 =F}}</ref> |
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==See also== |
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* ] |
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* ] |
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* ] |
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==References== |
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==Derivative== |
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A ] of spermine, N<sup>1</sup>, N<sup>12</sup>-bis(ethyl)spermine (also known as BESm) was investigated in the late 1980s along with similar ] for its potential as a ].<ref>{{cite journal |last1=Porter |first1=Carl W. |last2=McManis |first2=Jim |last3=Casero |first3=Robert A. |last4=Bergeron |first4=Raymond J. |title=Relative Abilities of Bis(ethyl) Derivatives of Putrescine, Spermidine, and Spermine to Regulate Polyamine Biosynthesis and Inhibit L1210 Leukemia Cell Growth |journal=Cancer Research |volume=47 |year=1987 |issue=11 |pages=2821–5 |pmid=3567905 |url=http://cancerres.aacrjournals.org/content/canres/47/11/2821.full.pdf}}</ref><ref>{{cite journal |last1=Pegg |first1=Anthony E. |last2=Wechter |first2=Rita |last3=Pakala |first3=Rajbabu |last4=Bergeron |first4=Raymond J. |title=Effect of N<sup>1</sup>, N<sup>12</sup>-Bis(ethyl)spermine and Related Compounds on Growth and Polyamine Acetylation, Content, and Excretion in Human Colon Tumor Cells |journal=Journal of Biological Chemistry |volume=264 |issue=20 |year=1989 |pages=11744–11749 |doi=10.1016/S0021-9258(18)80128-4 |pmid=2745415 |url=http://www.jbc.org/content/264/20/11744.full.pdf|doi-access=free }}</ref> |
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{{reflist}} |
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==Further reading== |
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==Biosynthesis== |
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*Slocum, R. D., Flores, H. E., "Biochemistry and Physiology of Polyamines in Plants", CRC Press, 1991, USA, ISBN 0-8493-6865-0 |
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Spermine biosynthesis in animals starts with ] of ] by the enzyme ] in the presence of ]. This decarboxylation gives ]. Thereafter the ] ] effects two ] by ]. The intermediate is ]. |
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*Uriel Bachrach, "The Physiology of Polyamines", CRC Press, 1989, USA, ISBN 0-8493-6808-1 |
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Plants employ additional routes to spermine. In one pathway L-glutamine is the precursor to L-ornithine, after which the synthesis of spermine from L-ornithine follows the same pathway as in animals. |
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Another pathway in plants starts with decarboxylation of L-arginine to produce ]. The imine functional group in agmatine then is hydrolysed by ], releasing ], converting the ] group into a urea. The resulting ] is acted on by a ] to split off the urea group, leaving ]. After that the putrescine follows the same pathway to completing the synthesis of spermine.<ref>{{cite book|last1=Dewick|first1=Paul M|title=Medicinal Natural Products: a biosynthetic approach|date=2009|publisher=Wiley|location=Chichester U.K.|isbn=9780470742761|page=312|edition=3rd}}</ref> |
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==References== |
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{{biochem-stub}} |
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{{Reflist}} |
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==Further reading== |
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] |
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* Slocum, R. D., Flores, H. E., "Biochemistry and Physiology of Polyamines in Plants", CRC Press, 1991, USA, {{ISBN|0-8493-6865-0}} |
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* Uriel Bachrach, "The Physiology of Polyamines", CRC Press, 1989, USA, {{ISBN|0-8493-6808-1}} |
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