Art. -Nr.: HY-14572

PR-104A

(Synonyms: SN 27858)

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PR-104A (SN 27858) is the alcohol metabolite of phosphate proagent PR-104. PR-104A is a hypoxia-selective DNA cross-linking agent/DNA-damaging agent and cytotoxin. Antitumor Activity. PR-104A is metabolized under hypoxia by the 1-electron NADPH:cytochrome P450 oxidoreductase. PR-104A can be used for the research of relapsed/refractory T-lineage acute lymphoblastic leukemia (T-ALL).

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Reinheit: 98.98%
CAS. Nr.: 680199-06-8
Formel: C₁₄H₁₉BrN₄O₉S
Molecular Weight:499.29

Speicherung:

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

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

PR-104A Chemical Structure

CAS. Nr.: 680199-06-8

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Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

PR-104A (SN 27858) is the alcohol metabolite of phosphate proagent PR-104. PR-104A is a hypoxia-selective DNA cross-linking agent/DNA-damaging agent and cytotoxin. Antitumor Activity^[1]. PR-104A is metabolized under hypoxia by the 1-electron NADPH:cytochrome P450 oxidoreductase. PR-104A can be used for the research of relapsed/refractory T-lineage acute lymphoblastic leukemia (T-ALL)^[2].

Cellular Effect

Cell Line	Type	Value	Description	References
DU-145	IC₅₀	210 μM Compound: 16; PR104A	Cytotoxicity against human DU145 cells assessed as reduction in cell viability incubated for 2 hrs under normoxic condition followed by washed with fresh media incubated for 3 days by alamar blue assay Cytotoxicity against human DU145 cells assessed as reduction in cell viability incubated for 2 hrs under normoxic condition followed by washed with fresh media incubated for 3 days by alamar blue assay	[PMID: 33220402]
DU-145	IC₅₀	78 μM Compound: 16; PR104A	Cytotoxicity against human DU145 cells assessed as reduction in cell viability incubated for 2 hrs under hypoxic condition followed washed with fresh media incubated for 3 days by alamar blue assay Cytotoxicity against human DU145 cells assessed as reduction in cell viability incubated for 2 hrs under hypoxic condition followed washed with fresh media incubated for 3 days by alamar blue assay	[PMID: 33220402]
HCT-116	IC₅₀	0.016 μM Compound: 1; PR-104A	Antiproliferative activity against human HCT-116 cells expressing NfsA of Escherichia coli assessed as cell growth inhibition measured after 4 hrs Antiproliferative activity against human HCT-116 cells expressing NfsA of Escherichia coli assessed as cell growth inhibition measured after 4 hrs	[PMID: 37974941]
HCT-116	IC₅₀	0.14 μM Compound: 1; PR-104A	Antiproliferative activity against human HCT-116 cells overexpressing cytochrome P450 oxidoreductase assessed as inhibition of cell growth incubated for 4 hrs under anoxic condition and measured after 5 days regrowth under aerobic condition Antiproliferative activity against human HCT-116 cells overexpressing cytochrome P450 oxidoreductase assessed as inhibition of cell growth incubated for 4 hrs under anoxic condition and measured after 5 days regrowth under aerobic condition	[PMID: 37974941]
HCT-116	IC₅₀	1.1 μM Compound: 1; PR-104A	Antiproliferative activity against human HCT-116 cells expressing AKR1C3 assessed as cell growth inhibition measured after 4 hrs Antiproliferative activity against human HCT-116 cells expressing AKR1C3 assessed as cell growth inhibition measured after 4 hrs	[PMID: 37974941]
HCT-116	IC₅₀	2.5 μM Compound: 1; PR-104A	Antiproliferative activity against human HCT-116 cells assessed as inhibition of cell growth incubated for 4 hrs under anoxic condition and measured after 5 days regrowth under aerobic condition Antiproliferative activity against human HCT-116 cells assessed as inhibition of cell growth incubated for 4 hrs under anoxic condition and measured after 5 days regrowth under aerobic condition	[PMID: 37974941]
HCT-116	IC₅₀	38 μM Compound: 1; PR-104A	Antiproliferative activity against human HCT-116 cells assessed as inhibition of cell growth incubated for 4 hrs under aerobic condition and measured after 5 days regrowth under aerobic condition Antiproliferative activity against human HCT-116 cells assessed as inhibition of cell growth incubated for 4 hrs under aerobic condition and measured after 5 days regrowth under aerobic condition	[PMID: 37974941]
HCT-116	IC₅₀	41 μM Compound: 1; PR-104A	Antiproliferative activity against human HCT-116 cells overexpressing cytochrome P450 oxidoreductase assessed as inhibition of cell growth incubated for 4 hrs under aerobic condition and measured after 5 days regrowth under aerobic condition Antiproliferative activity against human HCT-116 cells overexpressing cytochrome P450 oxidoreductase assessed as inhibition of cell growth incubated for 4 hrs under aerobic condition and measured after 5 days regrowth under aerobic condition	[PMID: 37974941]
HCT-116	IC₅₀	66 μM Compound: 1; PR-104A	Antiproliferative activity against wild type human HCT-116 cells assessed as cell growth inhibition measured after 4 hrs Antiproliferative activity against wild type human HCT-116 cells assessed as cell growth inhibition measured after 4 hrs	[PMID: 37974941]
NCI-H1299	IC₅₀	0.048 μM Compound: 1; PR-104A	Antiproliferative activity against human NCI-H1299 cells expressing NfsA of Escherichia coli assessed as cell growth inhibition measured after 4 hrs Antiproliferative activity against human NCI-H1299 cells expressing NfsA of Escherichia coli assessed as cell growth inhibition measured after 4 hrs	[PMID: 37974941]
NCI-H1299	IC₅₀	114 μM Compound: 1; PR-104A	Antiproliferative activity against wild type human NCI-H1299 cells assessed as cell growth inhibition measured after 4 hrs Antiproliferative activity against wild type human NCI-H1299 cells assessed as cell growth inhibition measured after 4 hrs	[PMID: 37974941]
NCI-H1299	IC₅₀	7.4 μM Compound: 1; PR-104A	Antiproliferative activity against human NCI-H1299 cells expressing AKR1C3 assessed as cell growth inhibition measured after 4 hrs Antiproliferative activity against human NCI-H1299 cells expressing AKR1C3 assessed as cell growth inhibition measured after 4 hrs	[PMID: 37974941]
PC-3	IC₅₀	320 μM Compound: 16; PR104A	Cytotoxicity against human PC-3 cells assessed as reduction in cell viability incubated for 2 hrs under normoxic condition followed by washed with fresh media incubated for 3 days by alamar blue assay Cytotoxicity against human PC-3 cells assessed as reduction in cell viability incubated for 2 hrs under normoxic condition followed by washed with fresh media incubated for 3 days by alamar blue assay	[PMID: 33220402]
PC-3	IC₅₀	48 μM Compound: 16; PR104A	Cytotoxicity against human PC-3 cells assessed as reduction in cell viability incubated for 2 hrs under hypoxic condition followed by washed with fresh media incubated for 3 days by alamar blue assay Cytotoxicity against human PC-3 cells assessed as reduction in cell viability incubated for 2 hrs under hypoxic condition followed by washed with fresh media incubated for 3 days by alamar blue assay	[PMID: 33220402]
PC-3	IC₅₀	7.3 μM Compound: 16; PR104A	Cytotoxicity against human PC-3 cells assessed as reduction in cell viability preincubated for 4 hrs in hypoxia and further incubated for 5 days in fresh medium by SRB assay Cytotoxicity against human PC-3 cells assessed as reduction in cell viability preincubated for 4 hrs in hypoxia and further incubated for 5 days in fresh medium by SRB assay	[PMID: 33220402]
SiHa	IC₅₀	19 μM Compound: 1; PR-104A	Antiproliferative activity against human SiHa cells assessed as inhibition of cell growth incubated for 4 hrs under aerobic condition and measured after 5 days regrowth under aerobic condition Antiproliferative activity against human SiHa cells assessed as inhibition of cell growth incubated for 4 hrs under aerobic condition and measured after 5 days regrowth under aerobic condition	[PMID: 37974941]
SiHa	IC₅₀	2.7 μM Compound: 1; PR-104A	Antiproliferative activity against human SiHa cells assessed as inhibition of cell growth incubated for 4 hrs under anoxic condition and measured after 5 days regrowth under aerobic condition Antiproliferative activity against human SiHa cells assessed as inhibition of cell growth incubated for 4 hrs under anoxic condition and measured after 5 days regrowth under aerobic condition	[PMID: 37974941]

In Vitro

PR-104A (1-100 uM) shows antiproliferative potency in a panel of 10 human carcinoma cell lines following 4 hours exposures under aerobic and hypoxic conditions with the lowest IC₅₀ (0.51 μM) in H460 non-small cell lung cancer cells and highest (7.3 μM) in PC3 prostate cells^[1].
The phosphate ester PR-104 is rapidly converted in vivo to the alcohol PR-104A, a nitrogen mustard prodrug that is metabolised to hydroxylamine (PR-104H) and amine (PR-104M) DNA crosslinking agents by one-electron reductases in hypoxic cells and by aldo-keto reductase 1C3 independently of oxygen^[3].

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

Cell Proliferation Assay^[1]

Cell Line:

HT29 , HCT116, C33A SiHa A549, H460, H1299 ,PC3,SKOV3, A375 cells
Concentration:

0, 1, 10, 100 uM
Incubation Time:

4 hours under aerobic or hypoxic conditions
Result:

The lowest IC₅₀ (0.51 μM) in H460 non-small cell lung cancer cells and highest (7.3 μM) in PC3 prostate cells.

In Vivo

The phosphate ester "pre-prodrug" PR-104 is well tolerated in mice and converted rapidly to the corresponding prodrug PR-104A. H460 xenografts shows significant sensitivity to PR-104 (total dose 3.2 mmol/kg)^[1].

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

Animal Model:

Specific pathogen-free homozygous nude (CD1-Foxn1nu) mice with H460 xenografts^[1]
Dosage:

Daily (0.23 mmol/kg/dose; qd ×14) or weekly (1.07 mmol/kg/dose; qw ×3)
Administration:

I.p.
Result:

The single-agent activity against H460 tumors refractory to docetaxel, cisplatin, gemcitabine, and cyclophosphamide was particularly striking.
Compared a daily (qd ×14) versus weekly (qw ×3) schedule against the chemoresistant H460 xenograft model using the same total dose (3.2 mmol/kg) over 14 days, which was well tolerated using both schedules.

Chemical Information

CAS. Nr. 680199-06-8
Appearance Solid
Molecular Weight 499.29
Formel C₁₄H₁₉BrN₄O₉S
Color Light yellow to green yellow
SMILES

BrCCN(CCOS(=O)(C)=O)C1=C(C(NCCO)=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O
Synonyms

SN 27858
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

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

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

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 100 mg/mL (200.28 mM; Need ultrasonic; 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

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.0028 mL

10.0142 mL

20.0284 mL

5 mM

0.4006 mL

2.0028 mL

4.0057 mL

10 mM

0.2003 mL

1.0014 mL

2.0028 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 (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.

Molaritätsrechner

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

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 6.25 mg/mL (12.52 mM); Clear solution

This protocol yields a clear solution of ≥ 6.25 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (62.5 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: ≥ 6.25 mg/mL (12.52 mM); Clear solution

This protocol yields a clear solution of ≥ 6.25 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (62.5 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 6.25 mg/mL (12.52 mM); Clear solution

This protocol yields a clear solution of ≥ 6.25 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (62.5 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (277 KB)
SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 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)

Verweise

[1]. Adam V Patterson, et al. Mechanism of action and preclinical antitumor activity of the novel hypoxia-activated DNA cross-linking agent PR-104. Clin Cancer Res. 2007 Jul 1;13(13):3922-32. [Content Brief]

[2]. Donya Moradi Manesh, et al. AKR1C3 is a biomarker of sensitivity to PR-104 in preclinical models of T-cell acute lymphoblastic leukemia. Blood. 2015 Sep 3;126(10):1193-202. [Content Brief]

[3]. McKeage MJ, et al. A phase I trial of PR-104, a pre-prodrug of the bioreductive prodrug PR-104A, given weekly to solid tumour patients. BMC Cancer. 2011;11:432. Published 2011 Oct 7. [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

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.0028 mL	10.0142 mL	20.0284 mL	50.0711 mL
	5 mM	0.4006 mL	2.0028 mL	4.0057 mL	10.0142 mL
	10 mM	0.2003 mL	1.0014 mL	2.0028 mL	5.0071 mL
	15 mM	0.1335 mL	0.6676 mL	1.3352 mL	3.3381 mL
	20 mM	0.1001 mL	0.5007 mL	1.0014 mL	2.5036 mL
	25 mM	0.0801 mL	0.4006 mL	0.8011 mL	2.0028 mL
	30 mM	0.0668 mL	0.3338 mL	0.6676 mL	1.6690 mL
	40 mM	0.0501 mL	0.2504 mL	0.5007 mL	1.2518 mL
	50 mM	0.0401 mL	0.2003 mL	0.4006 mL	1.0014 mL
	60 mM	0.0334 mL	0.1669 mL	0.3338 mL	0.8345 mL
	80 mM	0.0250 mL	0.1252 mL	0.2504 mL	0.6259 mL
	100 mM	0.0200 mL	0.1001 mL	0.2003 mL	0.5007 mL

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PR-104A

Cell Cycle/DNA Damage Compound Library

Metabolism/Protease Compound Library

Anti-Cancer Compound Library

Anti-Aging Compound Library

Anti-Lung Cancer Compound Library

Anti-Blood Cancer Compound Library

Drug Metabolite Library

Anti-Hematopathy Compound Library

Bioactive Compound Library Max

MCE Bioactive Compound Library

Bioactive Compound Library

High-Throughput Bioactive Compound Library

Biologische Aktivität

Chemical Information

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

PR-104A

Cell Cycle/DNA Damage Compound Library

Metabolism/Protease Compound Library

Anti-Cancer Compound Library

Anti-Aging Compound Library

Anti-Lung Cancer Compound Library

Anti-Blood Cancer Compound Library

Drug Metabolite Library

Anti-Hematopathy Compound Library

Bioactive Compound Library Max

MCE Bioactive Compound Library

Bioactive Compound Library

High-Throughput Bioactive Compound Library

Biologische Aktivität

Chemical Information

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

PR-104A Related Classifications

HY-14572 Related Classifications