Cat. No.: HY-101677

cPrPMEDAP

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cPrPMEDAP is an intermediate metabolite of GS-9219. cpr-PMEDAP functions as a proagent of the guanine nucleotide analog PMEG and has antiproliferative activity. cPrPMEDAP is negatively charged at physiologic pH and has poor permeability into the skin.

For research use only. We do not sell to patients.

Purity: 99.62%
CAS No.: 182798-83-0
Formula: C₁₁H₁₇N₆O₄P
Molecular Weight:328.26

Storage:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

cPrPMEDAP Chemical Structure

CAS No.: 182798-83-0

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Use of MCE Products

Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- Cellular Effect
- In Vitro
Chemical Information
Solvent & Solubility
- In Vitro
Purity & Documentation
References
Help & FAQs
Classifications
Bioz

Biological Activity

Description

Cellular Effect

Cell Line	Type	Value	Description	References
Ca-Ski	EC₅₀	1410 nM Compound: cPrPMEDAP	Antiproliferative activity against HPV-transformed human CaSki cells after 7 days by SRB assay Antiproliferative activity against HPV-transformed human CaSki cells after 7 days by SRB assay	[PMID: 19398642]
CCRF-HSB-2	CC₅₀	3 μM Compound: PME-cPrDAP	Cytotoxicity against human HSB2 cell after 4 hrs by MTS assay Cytotoxicity against human HSB2 cell after 4 hrs by MTS assay	[PMID: 18852272]
Daudi	CC₅₀	20 μM Compound: PME-cPrDAP	Cytotoxicity against human Daudi cell after 4 hrs by MTS assay Cytotoxicity against human Daudi cell after 4 hrs by MTS assay	[PMID: 18852272]
HeLa	EC₅₀	6930 nM Compound: cPrPMEDAP	Antiproliferative activity against HPV-transformed human HeLa cells after 7 days by SRB assay Antiproliferative activity against HPV-transformed human HeLa cells after 7 days by SRB assay	[PMID: 19398642]
HFF	CC₅₀	>100 μM Compound: PME-cPrDAP	Cytotoxicity against human HFF cells after 7 days by neutral red dye method Cytotoxicity against human HFF cells after 7 days by neutral red dye method	[PMID: 18852272]
HFF	CC₅₀	150 μM Compound: PME-cPrDAP	Cytotoxicity against human HFF cells Cytotoxicity against human HFF cells	[PMID: 18852272]
HFF	EC₅₀	<0.06 μM Compound: PME-cPrDAP	Antiviral activity against Murine cytomegalovirus Smith infected in HFF cells by plaque reduction assay Antiviral activity against Murine cytomegalovirus Smith infected in HFF cells by plaque reduction assay	[PMID: 18852272]
HFF	EC₅₀	0.4 μM Compound: PME-cPrDAP	Antiviral activity against Human cytomegalovirus AD169 infected in HFF cells by plaque reduction assay Antiviral activity against Human cytomegalovirus AD169 infected in HFF cells by plaque reduction assay	[PMID: 18852272]
HFF	EC₅₀	0.8 μM Compound: PME-cPrDAP	Antiviral activity against Varicella zoster virus Ellen infected in HFF cells by plaque reduction assay Antiviral activity against Varicella zoster virus Ellen infected in HFF cells by plaque reduction assay	[PMID: 18852272]
HFF	EC₅₀	4 μM Compound: PME-cPrDAP	Antiviral activity against herpes simplex virus 1 E-377 infected in HFF cells by plaque reduction assay Antiviral activity against herpes simplex virus 1 E-377 infected in HFF cells by plaque reduction assay	[PMID: 18852272]
HFF	EC₅₀	7.9 μM Compound: PME-cPrDAP	Antiviral activity against herpes simplex virus 2 MS infected in HFF cells by plaque reduction assay Antiviral activity against herpes simplex virus 2 MS infected in HFF cells by plaque reduction assay	[PMID: 18852272]
HT-3	EC₅₀	7040 nM Compound: cPrPMEDAP	Antiproliferative activity against HPV-non-transformed human HT3 cells after 7 days by SRB assay Antiproliferative activity against HPV-non-transformed human HT3 cells after 7 days by SRB assay	[PMID: 19398642]
ME-180	EC₅₀	8320 nM Compound: cPrPMEDAP	Antiproliferative activity against HPV-transformed human ME180 cells after 7 days by SRB assay Antiproliferative activity against HPV-transformed human ME180 cells after 7 days by SRB assay	[PMID: 19398642]
MOLT-3	CC₅₀	8.5 μM Compound: PME-cPrDAP	Cytotoxicity against human MOLT3 cell after 4 hrs by MTS assay Cytotoxicity against human MOLT3 cell after 4 hrs by MTS assay	[PMID: 18852272]
MOLT-3	EC₅₀	6.4 μM Compound: PME-cPrDAP	Antiviral activity against Human herpesvirus 6B Z29 infected in human MOLT-3 cells Antiviral activity against Human herpesvirus 6B Z29 infected in human MOLT-3 cells	[PMID: 18852272]
SCC-4	EC₅₀	1430 nM Compound: cPrPMEDAP	Antiproliferative activity against HPV-non-transformed human SCC4 cells after 7 days by SRB assay Antiproliferative activity against HPV-non-transformed human SCC4 cells after 7 days by SRB assay	[PMID: 19398642]
SCC-9	EC₅₀	10100 nM Compound: cPrPMEDAP	Antiproliferative activity against HPV-non-transformed human SCC9 cells after 7 days by SRB assay Antiproliferative activity against HPV-non-transformed human SCC9 cells after 7 days by SRB assay	[PMID: 19398642]
SiHa	EC₅₀	1500 nM Compound: cPrPMEDAP	Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 6 to 9 hrs by ELISA Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 6 to 9 hrs by ELISA	[PMID: 19398642]
SiHa	EC₅₀	1860 nM Compound: cPrPMEDAP	Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 3 to 6 hrs by ELISA Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 3 to 6 hrs by ELISA	[PMID: 19398642]
SiHa	EC₅₀	2300 nM Compound: cPrPMEDAP	Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 24 to 27 hrs by ELISA Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 24 to 27 hrs by ELISA	[PMID: 19398642]
SiHa	EC₅₀	2650 nM Compound: cPrPMEDAP	Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 48 to 51 hrs by ELISA Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 48 to 51 hrs by ELISA	[PMID: 19398642]
SiHa	EC₅₀	290 nM Compound: cPrPMEDAP	Antiproliferative activity against HPV-transformed human SiHa cells after 7 days by SRB assay Antiproliferative activity against HPV-transformed human SiHa cells after 7 days by SRB assay	[PMID: 19398642]
SiHa	EC₅₀	8840 nM Compound: cPrPMEDAP	Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 3 hrs by ELISA Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 3 hrs by ELISA	[PMID: 19398642]
SiHa	EC₅₀	>20000 nM Compound: cPrPMEDAP	Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 72 to 75 hrs by ELISA Inhibition of DNA synthesis in HPV-transformed human SiHa cells assessed as decrease in BrdU incorporation after 72 to 75 hrs by ELISA	[PMID: 19398642]

In Vitro

cPrPMEDAP shows antiproliferative activity in SiHa cells with an EC₅₀ of 290 nM (SiHa cells: HPV-transformed cervical carcinoma cell lines)^[1].
PMEG forms an active phosphorylated metabolite, PMEG diphosphate (PMEG-DP), in cells, which inhibits the growth of various transformed cell lines due to potent inhibition of the nuclear DNA polymerases α, δ and ?, resulting in inhibition of DNA synthesis and/or DNA repair. In animal models, PMEG has antiproliferative effects; the utility of PMEG as an antiproliferative agent is limited by its poor cellular permeability and toxicity. cPrPMEDAP has similar antiproliferative effects in vitro and reduced toxicity in vivo but, like PMEG, is negatively charged at physiologic pH and has poor permeability into the skin^[1].

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

Chemical Information

CAS No. 182798-83-0
Appearance Solid
Molecular Weight 328.26
Formula C₁₁H₁₇N₆O₄P
Color Off-white to light yellow
SMILES

NC1=NC(NC2CC2)=C3N=CN(CCOCP(O)(O)=O)C3=N1
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : 10 mg/mL (30.46 mM; ultrasonic and warming and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

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Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.0464 mL

15.2318 mL

30.4637 mL

5 mM

0.6093 mL

3.0464 mL

6.0927 mL

10 mM

0.3046 mL

1.5232 mL

3.0464 mL

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. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (272 KB)
SDS (251 KB)
- English - EN (251 KB)
- Français - FR (251 KB)
- Deutsch - DE (251 KB)
- Norwegian - NO (251 KB)
- Español - ES (251 KB)
- Swedish - SV (251 KB)
- Italian - IT (251 KB)
- Korean - KR (251 KB)
- Portuguese - PT (251 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Compton ML, et al. 9-(2-Phosphonylmethoxyethyl)-N6-cyclopropyl-2,6-diaminopurine (cpr-PMEDAP) as a prodrug of 9-(2-phosphonylmethoxyethyl)guanine (PMEG). Biochem Pharmacol. 1999;58(4):709-714. [Content Brief]

[2]. Wolfgang GH, et al. GS-9191 is a novel topical prodrug of the nucleotide analog 9-(2-phosphonylmethoxyethyl)guanine with antiproliferative activity and possible utility in the treatment of human papillomavirus lesions. Antimicrob Agents Chemother. 2009;53(7):2777-2784. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	3.0464 mL	15.2318 mL	30.4637 mL	76.1591 mL
	5 mM	0.6093 mL	3.0464 mL	6.0927 mL	15.2318 mL
	10 mM	0.3046 mL	1.5232 mL	3.0464 mL	7.6159 mL
	15 mM	0.2031 mL	1.0155 mL	2.0309 mL	5.0773 mL
	20 mM	0.1523 mL	0.7616 mL	1.5232 mL	3.8080 mL
	25 mM	0.1219 mL	0.6093 mL	1.2185 mL	3.0464 mL
	30 mM	0.1015 mL	0.5077 mL	1.0155 mL	2.5386 mL

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cPrPMEDAP

Anti-Infection Compound Library

Metabolism/Protease Compound Library

Drug Metabolite Library

Heterocyclic Compound Library

Bioactive Compound Library Max

MCE Bioactive Compound Library

Bioactive Compound Library

High-Throughput Bioactive Compound Library

Biological Activity

Chemical Information

Solvent & Solubility

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

cPrPMEDAP

Anti-Infection Compound Library

Metabolism/Protease Compound Library

Drug Metabolite Library

Heterocyclic Compound Library

Bioactive Compound Library Max

MCE Bioactive Compound Library

Bioactive Compound Library

High-Throughput Bioactive Compound Library

Biological Activity

Chemical Information

Solvent & Solubility

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

cPrPMEDAP Related Classifications

HY-101677 Related Classifications