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ITPP powder (Inositol Trispyrophosphate) is an experimental compound primarily investigated for its ability to regulate oxygen release from hemoglobin. It functions by lowering the oxygen‑binding affinity of hemoglobin, facilitating more efficient oxygen delivery from the bloodstream to oxygen‑deprived tissues, thus improving tissue oxygenation under hypoxic conditions. This mechanism gives it promising potential in areas such as physical performance enhancement, cardiovascular support, and the treatment of ischemia‑related disorders. At present, ITPP remains in the preclinical and early clinical research stage and has not obtained official marketing authorization from regulatory agencies including the FDA and EMA.
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ITPP COA
Molecular Structure and Chemical Composition
The molecular formula of ITPP (Myo-Inositol Trispyrophosphate) is C₆H₆Na₆O₂₁P₆, and its Chinese name is cyclohexahexanol cyclo1,2:3,4:5, 6-tris (P,P' -dihydrodiphosphate) hexasodium salt. Its core structure consists of three parts:
Cyclohexahexanol (inositol) : As a basic skeleton, it provides six hydroxyl groups (-OH) as connection sites for the phosphate group.
Tripyrophosphate groups: Each hydroxyl group is replaced by a pyrophosphate group (P₂O₇⁴⁻), forming three p-O-c bonds, which endow the molecule with strong negative charge and water solubility.
Physical Properties
Appearance and form: ITPP Powder is a white to off-white powder with no visible impurities, meeting the standards for pharmaceutical grade.
Solubility:Water solubility: Slightly soluble in water (dissolution assisted by ultrasound is required), and after dissolution, it presents as a transparent or slightly turbid solution.
Organic solvents: Insoluble in non-polar solvents such as ethanol and ether, but miscible with some polar organic solvents (such as DMSO).
Stability:Hygroscopicity: It has strong hygroscopicity and should be stored under dry and light-proof conditions (such as frozen storage at -20℃).
Thermal stability: Melting point > 270℃ (decomposition), indicating that its structure is stable at high temperatures and is suitable for industrial synthesis.
Chemical stability: Stable within the pH range of 5 to 9. Acidic or alkaline conditions may cause hydrolysis of the phosphate group.
Chemical Properties and Reactivity
Acid-base properties
ITPP is a strongly acidic salt (pKa≈0.3), which completely dissociates in water into hexasodium ions and inositol pyrophosphate anions.
It can react with strong acids (such as HCl) to form free acid forms, but the solubility of free acids is extremely low and they are prone to precipitation.
Phosphate group reaction
Hydrolysis reaction: Under acidic or alkaline conditions, the pyrophosphate group may gradually hydrolyze into monophosphoric acid or inorganic phosphoric acid, resulting in the loss of activity.
REDOX stability
The ITPP molecule contains no easily oxidized groups (such as unsaturated bonds and phenolic hydroxyl groups), and is stable to oxygen at normal temperature.
In the presence of strong oxidants (such as hydrogen peroxide), the oxidation of phosphate groups may be triggered, but this is rare in practical applications.
Relationship between Structure and Function
The core function of ITPP stems from its ability to regulate hemoglobin allosteria:
Allosteric effect
ITPP reduces the affinity of Hb for oxygen by non-covalently binding to the β subunit of hemoglobin (Hb) (the oxygen dissociation curve shifts to the right), promoting the release of oxygen in hypoxic tissues.
Structural foundation
Negative charge distribution: The strong negative charge of the pyrophosphate group interacts with the positive charge regions on the Hb surface to stabilize the allosteric conformation.
Steric hindrance: The rigid structure of the cyclohexanol skeleton restricts the movement of the Hb subunit, further regulating the oxygen-binding capacity.Chemical Considerations in Applications
Synthesis process
Usually, inositol is used as the raw material, and the pyrophosphate group is introduced through multi-step phosphorylation reactions, and finally the salt is purified.The key steps include the selection of phosphorylation reagents and the control of reaction conditions to avoid the formation of by-products.
Quality control
Purity: The main peak content detected by HPLC is ≥99%, and the total impurities are ≤0.5%.
Heavy metals and microorganisms: Comply with the standards of the Chinese Pharmacopoeia or USP (such as lead ≤0.1ppm, total bacterial count ≤1000CFU/g).
Storage and transportation
It should be stored in a dry and dark place to avoid moisture absorption and caking.
When transporting, it should be marked as "hygroscopic substance" to prevent contact with moist air.
ITPP powder, as a biologically active compound, its analytical methods need to cover key links such as purity determination, structural characterization, impurity control and stability study. The following systematically sorts out the core analytical methods of ITPP Powder from three dimensions: chemical analysis, instrumental analysis, and biological activity verification.
Purity determination: Ensure quality meets standards
High Performance Liquid Chromatography (HPLC)
Principle: By taking advantage of the retention characteristics of ITPP on a specific chromatographic column, quantitative analysis is conducted through comparison with standard substances.
Condition optimization: A C18 reversed-phase column was used, with the mobile phase being phosphate buffer (pH 6.8) - acetonitrile (95:5), and the detection wavelength being 220 nm. Under this condition, the separation degree of ITPP from impurities is good, with a linear range of 0.1-10 mg/mL and a recovery rate of 98%-102%.
Inductively coupled plasma Mass spectrometry (ICP-MS)
Objective: To detect heavy metal impurities (such as lead, arsenic, and mercury) in ITPP.
Method: After microwave digestion of the samples, germanium (Ge) was used as the internal standard, and the element concentration was determined by ICP-MS.
Standard: Comply with the requirements of the Chinese Pharmacopoeia or USP (such as lead ≤0.1 ppm, arsenic ≤0.2 ppm).
Karl Fischer moisture determination method
Principle: Based on the quantitative reaction between iodine and water, the moisture content is determined through titration.
Condition: Methanol is used as the solvent, and the titration endpoint is determined by potentiometry.
Meaning: ITPP is hygroscopic, and the moisture content should be controlled at ≤1.0% to prevent degradation.
Structural Characterization: Confirm molecular identity and conformation
1H NMR: In D2O, the proton signal of the cyclohexahexanol skeleton of ITPP appears at δ 3.5-4.5 ppm, and the proton of the pyrophosphate group shows a wide peak due to rapid exchange.
31P NMR: Shows the chemical shifts of three pyrophosphate groups (δ -10.2, -12.5, -14.8 ppm), and confirms the connection mode of the phosphate ester bond through the coupling constant.
Application: Verify molecular structure and conformation, and eliminate isomer interference.
Characteristic peak
3400 cm⁻¹ (O-H stretching vibration, inositol hydroxyl);
1250 cm⁻¹ (P=O stretching vibration, pyrophosphate group);
1050 cm⁻¹ (P-O-C stretching vibration, phosphate ester bond).
Significance: Rapidly confirm the functional groups of ITPP and assist in structural identification.
Objective: To analyze the crystal structure of ITPP.
Result: ITPP usually exists in amorphous or semi-crystalline form, while XRPD can eliminate crystalline impurities (such as unreacted inositol or sodium pyrophosphate).
Impurity Control: Ensuring Safety and Effectiveness
High-performance liquid chromatography-mass spectrometry (HPLC-MS)
Objective: To identify by-products during the synthesis process (such as monophosphate or inositol diphosphate derivatives).
Conditions: A C18 column was used, the mobile phase was formic acid-acetonitrile gradient elution, and the mass spectrometry detection mode was negative ion electrospray (ESI-).
Advantages: It can simultaneously achieve impurity separation and structural identification, with a sensitivity reaching the ppb level.
Thermogravimetric analysis (TGA)
Principle: The mass change of the sample is measured through programmed temperature rise to analyze thermal stability.
Result: ITPP is stable below 200℃, and its decomposition temperature is above 270℃, indicating good thermal stability and suitable for industrial synthesis.
Dissolution test
Method: Referring to the second method (paddle method) of Dissolution determination in the Chinese Pharmacopoeia, samples were taken using phosphate buffer solution with pH 7.4 as the medium, at a rotational speed of 50 rpm for 30 minutes.
Standard: ITPP dissolution rate ≥85% to ensure the bioavailability of the preparation.
Biological Activity Verification: Linking Chemical properties and Functions
Hemoglobin allosteric regulation experiment
Principle: ITPP promotes oxygen release by reducing the oxygen affinity of hemoglobin.
Method
Prepare human hemoglobin solution (20 μM);
Add ITPP (0-100 μM) and measure the oxygen dissociation curve;
Calculate the P50 value (the partial pressure of oxygen when the hemoglobin oxygen saturation is 50%).
Result: ITPP increased the P50 value from 26.5 mmHg to 35.2 mmHg, confirming its allosteric regulatory activity.
Cell hypoxia model experiment
Model: Use CoCl2 to induce hypoxia in HeLa cells.
Detection
Cell viability (MTT method)
Expression of hypoxia-inducible factor-1 α (HIF-1α) (Western blot)
Lactate level (enzymatic method).
Conclusion: ITPP (100 μM) can significantly reduce the expression of HIF-1α and lactic acid accumulation, and improve the hypoxia state of cells.
Its long‑term safety profile, optimal dosage, and potential risks in humans have not been fully established. While some animal studies have demonstrated improved exercise endurance and tissue oxygenation, high‑quality human clinical data remain limited, with reported concerns including hypotension and potential cardiovascular stress. ITPP is not approved as a legal dietary or sports supplement, and its use by athletes may carry anti‑doping rule violations. This compound is generally supplied only for scientific research purposes, and any non‑laboratory, off‑label application carries significant health and legal risks that require extreme caution.
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