NHC-triphosphate

Cat. No.: HY-135867: FAQs
Data Sheet SDS COA Handling Instructions

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NHC-triphosphate is an active phosphorylated intracellular metabolite of β-d-N4-Hydroxycytidine (NHC) (HY-125033) as a triphosphate form. NHC-triphosphate is a weak alternative substrate for the viral polymerase and can be incorporated into HCV replicon RNA.

At equivalent molar concentrations, both the salt and free forms of a compound exhibit comparable biological activity. Nevertheless, the salt form (NHC-triphosphate tetrasodium) usually boasts enhanced water solubility and stability.

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NHC-triphosphate Chemical Structure

CAS No. : 34973-27-8

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Other In-stock Forms of NHC-triphosphate:

NHC-diphosphate NHC-triphosphate tetraammonium

Other Forms of NHC-triphosphate:

5 Publications Citing Use of MCE NHC-triphosphate

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Biological Activity
Purity & Documentation
References
Customer Review

Description

NHC-triphosphate is an active phosphorylated intracellular metabolite of β-d-N4-Hydroxycytidine (NHC) (HY-125033) as a triphosphate form^[1]. NHC-triphosphate is a weak alternative substrate for the viral polymerase and can be incorporated into HCV replicon RNA^[1]^[2].

In Vitro

In an intracellular metabolism assay, HCV replicon cells are treated with 10 μM ³H-labeled NHC, and intracellular nucleotide levels are determined after 1, 2 and 8 hours incubations. NHC is rapidly convered into the mono-, di-, and triphosphate forms, and NHC-TP reaches up to 71.12 pM after 8 hours^[1].
NHC-triphosphate (NHC-TP) (5-40 μM) absence leads to full-length polymerization products, it can be a weak alternative substrate. In addition, incorporation of NHC-TP instead of CTP increases the molecular weight of the polymerization product by 16 (one extra oxygen) for each event and an obvious electrophoretic shift is observed in cell-free HCV NS5B polymerization reactions^[1].
Huh-7 cells are incubated with (10-50 μM; 4 h) NHC or a McGuigan phosphoramidate prodrug of NHC. Intracellular levels of the parental compounds and phosphorylated metabolites are measured using LC-MS/MS. Small amounts of NHC-monophosphate (MP) and NHC-diphosphate (DP) can be observed, while NHC-triphosphate (HY-135867) remains the most abundant metabolite^[2].
NHC-triphosphate (NHC-TP) metabolite may directly target the viral polymerase and behave as a nonobligate chain terminator. It plays a prominent role in inhibiting early negative-strand RNA synthesis, either through chain termination or mutagenesis, which may in turn interfere with correct replicase complex formation.

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

499.16

Formula

C₉H₁₆N₃O₁₅P₃

CAS No.

34973-27-8

Appearance

Solid

Color

White to off-white

SMILES

O[C@H]1[C@H](N(C=C/C2=N/O)C(N2)=O)O[C@H](COP(OP(OP(O)(O)=O)(O)=O)(O)=O)[C@H]1O

Structure Classification

Others

Initial Source

Endogenous metabolite

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

-20°C, protect from light, stored under nitrogen

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen)

Solvent & Solubility

In Vitro:

H₂O : 160 mg/mL (320.54 mM; Need ultrasonic)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	2.0034 mL	10.0168 mL	20.0337 mL
5 mM	0.4007 mL	2.0034 mL	4.0067 mL
10 mM	0.2003 mL	1.0017 mL	2.0034 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light, stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

In Vivo Dissolution Calculator

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Working solution concentration: mg/mL

This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only.If necessary, please contact MedChemExpress (MCE).

Purity & Documentation

Purity: 99.80%

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Data Sheet (275 KB) SDS (252 KB)

COA (249 KB) HNMR (258 KB) LCMS (150 KB)

Handling Instructions (2659 KB)

References

[1]. Stuyver LJ,et al. Ribonucleoside analogue that blocks replication of bovine viral diarrhea and hepatitis C viruses in culture.Antimicrob Agents Chemother. 2003 Jan;47(1):244-54. [Content Brief]

[2]. Maryam Ehteshami, et al. Characterization of β-d- N4-Hydroxycytidine as a Novel Inhibitor of Chikungunya Virus. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

H₂O	1 mM	2.0034 mL	10.0168 mL	20.0337 mL	50.0841 mL
	5 mM	0.4007 mL	2.0034 mL	4.0067 mL	10.0168 mL
	10 mM	0.2003 mL	1.0017 mL	2.0034 mL	5.0084 mL
	15 mM	0.1336 mL	0.6678 mL	1.3356 mL	3.3389 mL
	20 mM	0.1002 mL	0.5008 mL	1.0017 mL	2.5042 mL
	25 mM	0.0801 mL	0.4007 mL	0.8013 mL	2.0034 mL
	30 mM	0.0668 mL	0.3339 mL	0.6678 mL	1.6695 mL
	40 mM	0.0501 mL	0.2504 mL	0.5008 mL	1.2521 mL
	50 mM	0.0401 mL	0.2003 mL	0.4007 mL	1.0017 mL
	60 mM	0.0334 mL	0.1669 mL	0.3339 mL	0.8347 mL
	80 mM	0.0250 mL	0.1252 mL	0.2504 mL	0.6261 mL
	100 mM	0.0200 mL	0.1002 mL	0.2003 mL	0.5008 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.