ITPP (Myo-inositol trispyrophosphate)

ITPP (Myo-inositol trispyrophosphate)

ITPP (Myo-inositol trispyrophosphate)

ITPP (Myo-inositol trispyrophosphate)

ITPP (myo-inositol trispyrophosphate) is a synthetic membrane-permeable allosteric effector of hemoglobin engineered to increase tissue oxygenation under hypoxic conditions. By binding allosterically to the central cavity of hemoglobin tetramers, ITPP stabilizes deoxyhemoglobin, right-shifting the oxygen-hemoglobin dissociation curve to raise P50. This facilitates targeted oxygen release into hypoxic microenvironments without stimulating erythropoiesis or altering hematocrit.

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What is ITPP (myo-Inositol Trispyrophosphate)?

ITPP (known chemically as myo-inositol trispyrophosphate, hexasodium myo-inositol 1,6:2,3:4,5-tri-O-diphosphate, or OPP-111) is a lipophilic, membrane-permeable synthetic organic phosphate derivative. Developed as a targeted allosteric modulator of hemoglobin, ITPP penetrates red blood cell membranes to bind the central cavity of hemoglobin molecules, decreasing oxygen binding affinity in a controlled, reversible manner.

Unlike conventional metabolic modulators that act on nuclear receptors or kinase cascades, ITPP alters the physical thermodynamics of oxygen transport. By stabilizing the low-affinity T-state (deoxyhemoglobin), ITPP right-shifts the oxygen-hemoglobin dissociation curve, elevating the P50 value (the partial pressure of oxygen at which hemoglobin is 50% saturated). This significantly increases oxygen (O2) offloading into oxygen-deprived or ischemic tissues without reducing arterial oxygen loading in the lungs (SaO2).

Batch-verified for high analytical purity at Modern Aminos, ITPP is offered as a standardized reference material for cell culture and biochemical research. Researchers evaluating tissue hypoxia attenuation, tumor re-oxygenation kinetics, and oxygen-dependent bioenergetics utilize ITPP alongside complementary metabolic reference standards available on the site, such as AICAR, GW-501516 (Cardarine), SLU-PP-332, and BAM15.

Chemical and Molecular Data

Compound Name ITPP (myo-Inositol Trispyrophosphate Hexasodium)
Quantity / Formats Offered High-Purity Dry Reference Powder / Solid Unit Material
Chemical Structure Synthetic Inositol Phosphate Pyrophosphate Salt
Synonyms / Alt Names myo-inositol trispyrophosphate, ITPP, OPP-111, OXY111, Hexasodium myo-inositol 1,6:2,3:4,5-tri-O-diphosphate
CAS Number 1000242-70-1 (Hexasodium) | 362828-82-5 (Free Acid)
Chemical Formula C6H6Na6O18P6 (Hexasodium Salt)
Molecular Weight 671.88 g/mol (Hexasodium Salt) | 540.01 g/mol (Free Acid)
IUPAC Name hexasodium; 2,3,4,5,6,7-hexaoxa-1,3,5-triphosphabicyclo[2.2.1]heptane 1,3,5-trioxide derivative
InChIKey InChIKey=JKGJSQYRHQJFFP-UHFFFAOYSA-H
SMILES Code [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].O=P1(O[C@@H]2[C@H](OP(=O)(O1)O[C@@H]3[C@H]2OP(=O)(O3)O[C@@H]4[C@H]3OP(=O)(O4)O)O)O

What are the Mechanisms of Action?

The biochemical pathways and cellular targets of ITPP (myo-inositol trispyrophosphate) in laboratory research include:

  • Allosteric Hemoglobin Modulation & P50 Right-Shift: ITPP crosses erythrocyte membranes to bind the 2,3-bisphosphoglycerate (2,3-BPG) allosteric pocket of hemoglobin. By stabilizing the deoxy-conformation (T-state), ITPP increases the P50 of hemoglobin (e.g., from ≈ 26 mmHg up to ≈ 40–50 mmHg in experimental models), enhancing oxygen dissociation in low P50 microenvironments.
  • Targeted Oxygen Offloading in Hypoxic Tissues: Because high oxygen partial pressure (pO50) in pulmonary capillaries maintains full hemoglobin saturation (SaO2), ITPP does not impair oxygen loading in lungs. When erythrocyte complexes pass through hypoxic peripheral tissue capillaries (pO50 < 30 mmHg), the elevated P50 accelerates O2 release, restoring cellular respiration.
  • Erythropoietin-Independent Oxygenation: Unlike erythropoietin (EPO) or hypoxia-inducible factor (HIF) stabilizers, ITPP enhances tissue oxygen delivery without increasing red blood cell count, hematocrit, or plasma viscosity, eliminating polycythemia-associated hemodynamic resistance in fluid flow models.

What do Preclinical & Academic Studies Show for ITPP (Myo-inositol trispyrophosphate)?

When evaluating research efficacy and published scientific literature for ITPP (myo-inositol trispyrophosphate):

  • Allosteric Hemoglobin Kinetics & Maximal Respiration (PubMed): Landmark bioenergetic studies cataloged on PubMed (PMID: 19139414) demonstrate that ITPP (Myo-inositol trispyrophosphate) administration increases exercise capacity and maximal oxygen consumption (VO2max) in cardiovascular disease models by enhancing peripheral O2 extraction efficiency.
  • Tumor Re-Oxygenation & Ischemic Perfusion (PMC): Comprehensive biomedical reviews archived in PMC (PMC2638883) document ITPP’s capacity to reduce tumor hypoxia, downregulate HIF-1α transcription, and restore normoxic signaling in ischemic tissue models.
  • Chemical Profiling & Identification (PubChem): Official structural characterization maintained on PubChem verifies the molecular mass (671.88 g/mol hexasodium salt), inositol trispyrophosphate ring geometry, and HPLC mass spectrometry profile of CAS 1000242-70-1.

How does ITPP (Myo-inositol trispyrophosphate) compare to other compounds?

To evaluate oxygen delivery mechanisms, metabolic pathways, and bioenergetic targets, researchers compare ITPP against alternative reference standards available at Modern Aminos:

ITPP vs. Erythropoietin (EPO) & Hematological Modulators

In hypoxia and performance-modeling research, the mechanism of oxygen delivery dictates physiological response:

  • ITPP (myo-Inositol Trispyrophosphate): Allosteric hemoglobin effector. Increases oxygen delivery per red blood cell by right-shifting the P50 curve and accelerating O2 release in low pO2 microvessels, without changing hematocrit, RBC volume, or blood viscosity.
  • Erythropoietin (EPO) / Recombinant EPO: Hematopoietic hormone. Increases oxygen transport by stimulating bone marrow erythropoiesis to expand total red blood cell mass, which significantly elevates blood viscosity and vascular resistance.
Compound / Reference Chemical Structure & Class Core Mechanism of Action Research Focus & Profile
ITPP (myo-Inositol Trispyrophosphate) Synthetic Membrane-Permeable Inositol Phosphate Salt Allosteric effector of hemoglobin; increases P50 to accelerate O2 offloading into hypoxic microenvironments Focuses on tissue oxygenation, P50 curve right-shifting, ischemic re-oxygenation, and erythropoietin-independent respiration
AICAR Nucleoside Analog Master AMPK Agonist Mimics AMP to directly activate AMP-activated protein kinase (AMPK) independent of cellular ATP levels Focuses on master metabolic switch activation, glucose uptake, GLUT4 translocation, and metabolic signaling pathways
GW-501516 (Cardarine) PPARδ Selective Agonist Recruits PGC-1α via PPARδ to upregulate skeletal muscle fatty acid beta-oxidation and PDK4 expression Focuses on PPARδ nuclear receptor signaling, fatty acid transport (FAT/CD36), and glycogen sparing in myocytes
SLU-PP-332 Pan-ERR Nuclear Receptor Agonist Binds ERRα/β/γ receptors to recruit PGC-1α and upregulate mitochondrial OXPHOS gene transcription Focuses on nuclear receptor exercise mimetics, oxidative muscle fiber switching, and de novo mitochondrial biogenesis

Frequently Asked Questions (FAQs)

1. Is Modern Aminos a reliable place to buy ITPP (myo-inositol trispyrophosphate)?

Yes, Modern Aminos is a highly trusted vendor for high-purity research chemicals and reference compounds. Every batch of ITPP (myo-inositol trispyrophosphate) undergoes strict third-party analytical testing (including HPLC and Mass Spectrometry) to verify minimum 98%+ chemical purity, correct molecular weight (671.88 g/mol hexasodium salt), exact allosteric structure fidelity, and complete absence of heavy metals or synthesis impurities.

2. What is ITPP (myo-inositol trispyrophosphate) and how is it classified chemically?

ITPP (myo-inositol trispyrophosphate) is a synthetic membrane-permeable inositol phosphate derivative. It is classified chemically as an allosteric effector of hemoglobin designed to modulate oxygen transport kinetics in red blood cells.

3. How does ITPP modulate hemoglobin allosteric kinetics and P50 values?

ITPP binds allosterically within the central cavity of hemoglobin tetramers, stabilizing the low-affinity T-state (deoxyhemoglobin). This right-shifts the oxygen-hemoglobin dissociation curve, elevating P50 and promoting O2 release in low pO2 tissue capillaries.

4. How does ITPP facilitate oxygen delivery without increasing hematocrit or RBC count?

Unlike erythropoietin (EPO), which stimulates red blood cell production in bone marrow, ITPP acts directly on existing hemoglobin molecules. It increases the volume of oxygen released per erythrocyte passage without altering total blood volume or plasma viscosity.

5. What role does ITPP (Myo-inositol trispyrophosphate) play in tissue hypoxia and tumor microenvironment research?

In hypoxic tissue models, ITPP accelerates local O2 offloading, restoring aerobic metabolism and suppressing hypoxia-inducible factor 1-alpha (HIF-1α) expression. In tumor models, ITPP reduces core hypoxia, altering tumor vascularization and metabolic stress signaling.

6. How does ITPP compare to metabolic exercise mimetics like AICAR or SLU-PP-332?

AICAR (AMPK agonist) and SLU-PP-332 (pan-ERR agonist) act intracellularly on enzymatic and nuclear receptor transcription pathways. ITPP operates biophysically on circulating red blood cells to enhance extracellular O2 availability to tissues.

7. How does Modern Aminos verify the chemical purity and identity of ITPP (Myo-inositol trispyrophosphate)?

Modern Aminos utilizes High-Performance Liquid Chromatography (HPLC) to confirm active chemical purity exceeding 99% and Mass Spectrometry (MS) to verify exact molecular weight (671.88 g/mol hexasodium salt) and structural identity prior to batch release.

8. What are the recommended storage parameters for ITPP reference standards?

Dry reference material should be stored tightly sealed in a cool, dry environment (15°C to 25°C) or refrigerated for long-term preservation. Protect from direct heat, light exposure, and atmospheric moisture to maintain solid-state chemical stability.

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