Chemistry:Myo-inositol trispyrophosphate
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3D model (JSmol)
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| MeSH | C516441 |
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| 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). | |
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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
ITPP is a pyrophosphate derivative of phytic acid with the molecular formula C6H12O21P6.[1]
Biological effects
ITPP is a membrane-permeant allosteric regulator of hemoglobin 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
- Phytic acid
- Inositol
- Inositol phosphate
- Inositol trisphosphate
- myo-Inositol
References
- ↑ 1.0 1.1 1.2 1.3 1.4 Biolo, A; Greferath, R; Siwik, DA; Qin, F; Valsky, E; Fylaktakidou, KC; Pothukanuri, S; Duarte, CD et al. (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. doi:10.1073/pnas.0812381106. PMID 19204295. Bibcode: 2009PNAS..106.1926B.
- ↑ 2.0 2.1 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 et al. (2017). "The Allosteric Hemoglobin Effector ITPP Inhibits Metastatic Colon Cancer in Mice.". Ann. Surg. 266 (5): 746–753. doi:10.1097/SLA.0000000000002431. PMID 28742687. https://www.zora.uzh.ch/id/eprint/139098/1/95978.pdf.
- ↑ 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. PMID 27756258.
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