Jump to content
 







Main menu
   


Navigation  



Main page
Contents
Current events
Random article
About Wikipedia
Contact us
Donate
 




Contribute  



Help
Learn to edit
Community portal
Recent changes
Upload file
 








Search  

































Create account

Log in
 









Create account
 Log in
 




Pages for logged out editors learn more  



Contributions
Talk
 



















Contents

   



(Top)
 


1 Chemistry  





2 Biological effects  





3 See also  





4 References  














myo-Inositol trispyrophosphate







Add links
 









Article
Talk
 

















Read
Edit
View history
 








Tools
   


Actions  



Read
Edit
View history
 




General  



What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Cite this page
Get shortened URL
Download QR code
Wikidata item
 




Print/export  



Download as PDF
Printable version
 
















Appearance
   

 






From Wikipedia, the free encyclopedia
 

(Redirected from Myo-inositol trispyrophosphate)

myo-Inositol trispyrophosphate
Chemical structure of ITPP
Names
Other names

  • ITPP
  • myo-Inositol cyclic 1,2:3,4:5,6-tris(dihydrogen pyrophosphate)
  • myo-Inositol cyclic 1,2:3,4:5,6-tris(P,P'-dihydrogen diphosphate)
  • Hexahydrobis[1,3,5,2,4]trioxadiphosphepino[6,7-g:6',7'-i][1,3,5,2,4]benzotrioxadiphosphepine-2,4,7,9,12,14-hexol 2,4,7,9,12,14-hexaoxide
  • Identifiers

    CAS Number

    3D model (JSmol)

    ChemSpider
    MeSH C516441

    PubChem CID

    • InChI=1S/C6H12O21P6/c7-28(8)19-1-2(20-29(9,10)25-28)4-6(24-33(17,18)27-32(15,16)23-4)5-3(1)21-30(11,12)26-31(13,14)22-5/h1-6H,(H,7,8)(H,9,10)(H,11,12)(H,13,14)(H,15,16)(H,17,18)

      Key: HEDKSUBRULAYNO-UHFFFAOYSA-N

    • InChI=1S/C6H12O21P6/c7-28(8)19-1-2(20-29(9,10)25-28)4-6(24-33(17,18)27-32(15,16)23-4)5-3(1)21-30(11,12)26-31(13,14)22-5/h1-6H,(H,7,8)(H,9,10)(H,11,12)(H,13,14)(H,15,16)(H,17,18)

      Key: HEDKSUBRULAYNO-UHFFFAOYSA-N

    • C12C(C3C(C4C1OP(=O)(OP(=O)(O4)O)O)OP(=O)(OP(=O)(O3)O)O)OP(=O)(OP(=O)(O2)O)O

    Properties

    Chemical formula

    C6H12O21P6
    Molar mass 605.984 g·mol−1

    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    Infobox references

    myo-Inositol trispyrophosphate (ITPP) is an inositol phosphate, a pyrophosphate, a drug candidate, and a putative performance-enhancing substance, which exerts its biological effects by increasing tissue oxygenation.[1]

    Chemistry

    [edit]

    ITPP is a pyrophosphate derivativeofphytic acid with the molecular formula C6H12O21P6.[1]

    Biological effects

    [edit]

    ITPP is a membrane-permeant allosteric regulatorofhemoglobin that mildly reduces its oxygen-binding affinity, which shifts the oxygen-hemoglobin dissociation curve to the right and thereby increases oxygen release from the blood into tissue.[1] Phytic acid, in contrast, is not membrane-permeant due to its charge distribution.[1]

    Rodent studies in vivo demonstrated increased tissue oxygenation and dose-dependent increases in endurance during physical exercise, in both healthy mice and transgenic mice expressing a heart failure phenotype.[1]

    The substance is believed to have a high potential for use in athletic doping, and liquid chromatography–mass spectrometry tests have been developed to detect ITPP in urine tests.[2] Its use as a performance-enhancing substance in horse racing has also been suspected and similar tests have been developed for horses[3]

    ITPP has been studied for potential adjuvant use in the treatment of cancer in conjunction with chemotherapy, due to its effects in reducing tissue hypoxia.[4] Human clinical trials were registered in 2014 under the compound number OXY111A.[5] The substance has also been examined in the context of other illnesses involving hypoxia, such as cardiovascular disease and dementia[2]

    See also

    [edit]

    References

    [edit]
    1. ^ a b c d e Biolo, A; Greferath, R; Siwik, DA; Qin, F; Valsky, E; Fylaktakidou, KC; Pothukanuri, S; Duarte, CD; Schwarz, RP; Lehn, JM; Nicolau, C; Colucci, WS (2009). "Enhanced exercise capacity in mice with severe heart failure treated with an allosteric effector of hemoglobin, myo-inositol trispyrophosphate". Proc Natl Acad Sci U S A. 106 (6): 1926–1929. Bibcode:2009PNAS..106.1926B. doi:10.1073/pnas.0812381106. PMC 2644140. PMID 19204295.
  • ^ a b Görgens, C; Guddat, S; Schänzer, W; Thevis, M (2014). "Screening and confirmation of myo-inositol trispyrophosphate (ITPP) in human urine by hydrophilic interaction liquid chromatography high resolution / high accuracy mass spectrometry for doping control purposes". Drug Test. Anal. 6 (11–12): 1102–1107. doi:10.1002/dta.1700. PMID 25070041.
  • ^ Lam, G; Zhao, S; Sandhu, J; Yi, R; Loganathan, D; Morrissey, B (2014). "Detection of myo-inositol tris pyrophosphate (ITPP) in equine following an administration of ITPP". Drug Test. Anal. 6 (3): 268–276. doi:10.1002/dta.1473. PMID 23733541.
  • ^ Limani, P; Linecker, M; Schneider, MA; Kron, P; Tschuor, C; Kachaylo, E; Ungethuem, U; Nicolau, C; Lehn, JM; Graf, R; Humar, B; Clavien, PA (2017). "The Allosteric Hemoglobin Effector ITPP Inhibits Metastatic Colon Cancer in Mice" (PDF). Ann. Surg. 266 (5): 746–753. doi:10.1097/SLA.0000000000002431. PMID 28742687. S2CID 20565432.
  • ^ Limani, P; Linecker, M; Kron, P (2016). "Development of OXY111A, a novel hypoxia-modifier as a potential antitumor agent in patients with hepato-pancreato-biliary neoplasms - Protocol of a first Ib/IIa clinical trial". BMC Cancer. 16 (1): 812. doi:10.1186/s12885-016-2855-3. PMC 5070093. PMID 27756258.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Myo-Inositol_trispyrophosphate&oldid=1202809082"

    Categories: 
    Phospholipids
    Inositol
    Signal transduction
    Hidden categories: 
    Articles without EBI source
    Articles without KEGG source
    Articles without UNII source
    Articles containing unverified chemical infoboxes
    Articles with short description
    Short description matches Wikidata
     



    This page was last edited on 3 February 2024, at 15:23 (UTC).

    Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.



    Privacy policy

    About Wikipedia

    Disclaimers

    Contact Wikipedia

    Code of Conduct

    Developers

    Statistics

    Cookie statement

    Mobile view



    Wikimedia Foundation
    Powered by MediaWiki