Home DNA Damage/DNA Repair DNA/RNA Synthesis inhibitor - RNR inhibitor Triapine (3-AP) For research use only.

Triapine (3-AP)

Triapine (3-AP) is a potent ribonucleotide reductase (RNR) inhibitor with broad spectrum antitumor activity by inhibiting DNA synthesis. Phase 2.

Triapine (3-AP) Chemical Structure

Triapine (3-AP) Chemical Structure

CAS No. 200933-27-3

Purity & Quality Control

Triapine (3-AP) Related Products

Signaling Pathway

DNA/RNA Synthesis Signaling Pathways

DNA/RNA Synthesis Signaling Pathway

Cell Data

Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
SK-N-MC Antiproliferative assay Antiproliferative activity against human SK-N-MC cells by MTT assay, IC50=0.31μM 17142046
SK-N-MC Antiproliferative assay 72 hrs Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay, IC50=0.26μM 17602603
SK-N-MC Antiproliferative assay Antiproliferative activity against human SK-N-MC cells by MTT assay, IC50=0.54μM 17963372
BT-37 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells 18159922
KB-3-1 Cytotoxicity assay 72 hrs Cytotoxicity against human P-gp-negative KB-3-1 cells after 72 hrs by MTT assay, IC50=1.4μM 19397322
KB-3-1 Cytotoxicity assay 72 hrs Cytotoxicity against human P-gp-negative KB-3-1 cells after 72 hrs by MTT assay, IC50=1.41254μM 19397322
KBV1 Cytotoxicity assay 72 hrs Cytotoxicity against human P-glycoprotein-expressing KBV1 cells after 72 hrs by MTT assay, IC50=5.88844μM 19397322
KBV1 Cytotoxicity assay 72 hrs Cytotoxicity against human P-glycoprotein-expressing KBV1 cells after 72 hrs by MTT assay, IC50=5.9μM 19397322
SK-N-MC Antiproliferative assay 72 hrs Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay, IC50=0.26μM 19601577
HCT116 Dark cytotoxicity assay 96 hrs Dark cytotoxicity against human HCT116 cells expressing wild type p53 after 96 hrs by MTT assay, IC50=1.226μM 24900837
HCT116 Photocytotoxicity assay 24 hrs Photocytotoxicity against human HCT116 cells expressing wild type p53 incubated for 24 hrs followed by light irradiation measured after 24 hrs by MTS assay in presence of ALA and FeCl3 24900837
HCT116 Function assay 4 uM 24 hrs Induction of ROS generation in human HCT116 cells expressing wild type p53 at 4 uM after 24 hrs by spectrophotometry 24900837
NB-EBc1 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells 27336684
OHS-50 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells 27336684
KB-3-1 Cytotoxicity assay 72 hrs Cytotoxicity against human KB-3-1 cells incubated for 72 hrs by MTT assay, IC50=3.1μM 27336684
KBC1 Cytotoxicity assay 72 hrs Cytotoxicity against human KBC1 cells incubated for 72 hrs by MTT assay, IC50=8.9μM 27336684
SW480 Function assay 2.5 uM 48 hrs Induction of morphological changes in human SW480 cells assessed as induction of massive cell flattening at 2.5 uM incubated for 48 hrs by phase contrast microscopy 27336684
HL60 Function assay 1 and 5 uM 30 mins Induction of intracellular ROS generation in human HL60 cells at 1 and 5 uM in presence of CuCl2 incubated for 30 mins by DCF-DA staining based fluorescence assay 27336684
L1210 Growth inhibition assay Growth inhibition of mouse L1210 cells by MTS assay, IC50=1.3μM 30904782
SJ-GBM2 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells 31614257
WPMY-1 Antiproliferative assay 72 hrs Antiproliferative activity against human WPMY-1 cells assessed as reduction in cell proliferation incubated for 72 hrs by MTT assay, IC50=4.96μM 31614257
GES-1 Antiproliferative assay 72 hrs Antiproliferative activity against human GES-1 cells assessed as reduction in cell proliferation incubated for 72 hrs by MTT assay, IC50=5.6μM 31614257
HEK293 Cytotoxicity assay Cytotoxicity against HEK293 cells (CO-ADD:MA_007); CC50 by cell viability assay in DMEM (10% FBS) media using TC plates, by Resazurin F(560/590), CC50=2.827μM ChEMBL
GES-1 Cytotoxicity assay 72 hrs Cytotoxicity against human GES-1 cells after 72 hrs by MTT assay, IC50=5.4μM ChEMBL
MGC803 Antiproliferative assay 72 hrs Antiproliferative activity against human MGC803 cells after 72 hrs by MTT assay, IC50=9.68μM ChEMBL
MCF7 Antiproliferative assay 72 hrs Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay, IC50=18.85μM ChEMBL
SMMC7721 Antiproliferative assay 72 hrs Antiproliferative activity against human SMMC7721 cells after 72 hrs by MTT assay, IC50=42.81μM ChEMBL
Click to View More Cell Line Experimental Data

Biological Activity

Description Triapine (3-AP) is a potent ribonucleotide reductase (RNR) inhibitor with broad spectrum antitumor activity by inhibiting DNA synthesis. Phase 2.
Targets
Ribonucleotide reductase [1]
In vitro
In vitro Triapine potently inhibits the activity of ribonucleotide reductase in both wild-type KB and HU-resistant KB nasopharyngeal carcinoma cells. Triapine shows broad spectrum antitumor activity by inhibiting DNA synthesis in a series of cancer cell lines. [1] In vitro, Triapine blocks ischemic neurotoxicity and hypoxic toxicity with EC50 of 0.35 μM and 0.75 μM, respectively. Triapine also shows its neuroprotective activity by suppressing cell death induced by neurotoxic agents, including staurosporine, veratridine and glutamate. [2]
Kinase Assay Ribonucleotide reductase assay
CDP reductase is assayed using Dowex 1-borate ion-exchange chromatography. The assay mixture contains 0.02 μCi of [14C]CDP (52.9 mCi/mmol), 3 mM dithiothreitol, 6 mM MgCl2, 30 mM HEPES, 5 mM ATP, 0.15 mM unlabeled CDP, and 10 μL of cellular extract in a final volume of 0.02 mL. The incubation time for the reaction is 60 min, during which time the reaction is linear.
Cell Research Cell lines Wild-type KB and HU-resistant KB nasopharyngeal carcinoma cells.
Concentrations ~10 μM
Incubation Time A period of 3 generations
Method

Cells are plated at a density of 104 cells/mL per well in 24-well plates. Drugs are added to cells and incubations are continued for a period of 3 generations (untreated control cells), followed by assessment of cell growth by the methylene blue assay.
Experimental Result Images Methods Biomarkers Images PMID
Western blot p-Chk1 / Chk1 / p-CDK1/2 / CDK1/2 / p-H1 24413181
Growth inhibition assay Cell viability 31118677
In Vivo
In vivo In mice bearing the L1210 leukemia, Triapine (1.25 to 20 mg/kg) is curative for some mice without lethal toxicity. Triapine also inhibits the growth of solid tumors in mice M109 lung carcinoma and human A2780 ovarian carcinoma xenografts. In addition, combination of Triapine with various classes of agents that damage DNA results in synergistic inhibition of the L1210 leukemia. [1] In a rat model of transient ischemia, Triapine reduces infarct volume by 59% when administered i.c.v. (50 μ per rat) and by 35% when administered i.v. (1 mg/kg). [2]
Animal Research Animal Models BALB/cBA/2 (CD2F1) mice with the L1210 leukemia and the M109 lung carcinoma, athymic nu/nu mice with the human A2780 ovarian carcinoma xenograft.
Dosages ~24 mg/kg
Administration i.p. or i.v.
NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT00293345 Completed
Anaplastic Large Cell Lymphoma|Angioimmunoblastic T-cell Lymphoma|Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue|Intraocular Lymphoma|Nodal Marginal Zone B-cell Lymphoma|Primary Central Nervous System Hodgkin Lymphoma|Primary Central Nervous System Non-Hodgkin Lymphoma|Recurrent Adult Burkitt Lymphoma|Recurrent Adult Diffuse Large Cell Lymphoma|Recurrent Adult Diffuse Mixed Cell Lymphoma|Recurrent Adult Diffuse Small Cleaved Cell Lymphoma|Recurrent Adult Hodgkin Lymphoma|Recurrent Adult Immunoblastic Large Cell Lymphoma|Recurrent Adult Lymphoblastic Lymphoma|Recurrent Adult T-cell Leukemia/Lymphoma|Recurrent Cutaneous T-cell Non-Hodgkin Lymphoma|Recurrent Grade 1 Follicular Lymphoma|Recurrent Grade 2 Follicular Lymphoma|Recurrent Grade 3 Follicular Lymphoma|Recurrent Mantle Cell Lymphoma|Recurrent Marginal Zone Lymphoma|Recurrent Mycosis Fungoides/Sezary Syndrome|Recurrent Small Lymphocytic Lymphoma|Small Intestine Lymphoma|Splenic Marginal Zone Lymphoma|Stage III Adult Burkitt Lymphoma|Stage III Adult Diffuse Large Cell Lymphoma|Stage III Adult Diffuse Mixed Cell Lymphoma|Stage III Adult Diffuse Small Cleaved Cell Lymphoma|Stage III Adult Hodgkin Lymphoma|Stage III Adult Immunoblastic Large Cell Lymphoma|Stage III Adult Lymphoblastic Lymphoma|Stage III Adult T-cell Leukemia/Lymphoma|Stage III Cutaneous T-cell Non-Hodgkin Lymphoma|Stage III Grade 1 Follicular Lymphoma|Stage III Grade 2 Follicular Lymphoma|Stage III Grade 3 Follicular Lymphoma|Stage III Mantle Cell Lymphoma|Stage III Marginal Zone Lymphoma|Stage III Mycosis Fungoides/Sezary Syndrome|Stage III Small Lymphocytic Lymphoma|Stage IV Adult Burkitt Lymphoma|Stage IV Adult Diffuse Large Cell Lymphoma|Stage IV Adult Diffuse Mixed Cell Lymphoma|Stage IV Adult Diffuse Small Cleaved Cell Lymphoma|Stage IV Adult Hodgkin Lymphoma|Stage IV Adult Immunoblastic Large Cell Lymphoma|Stage IV Adult Lymphoblastic Lymphoma|Stage IV Adult T-cell Leukemia/Lymphoma|Stage IV Cutaneous T-cell Non-Hodgkin Lymphoma|Stage IV Grade 1 Follicular Lymphoma|Stage IV Grade 2 Follicular Lymphoma|Stage IV Grade 3 Follicular Lymphoma|Stage IV Mantle Cell Lymphoma|Stage IV Marginal Zone Lymphoma|Stage IV Mycosis Fungoides/Sezary Syndrome|Stage IV Small Lymphocytic Lymphoma|Unspecified Adult Solid Tumor Protocol Specific|Waldenström Macroglobulinemia
National Cancer Institute (NCI)
 June 2006 Phase 1

Chemical Information & Solubility

Molecular Weight 195.24 Formula

C7H9N5S
CAS No. 200933-27-3 SDF Download Triapine (3-AP) SDF
Smiles C1=CC(=C(N=C1)C=NNC(=S)N)N
Storage (From the date of receipt)

In vitro
Batch:

DMSO : 39 mg/mL ( (199.75 mM) Moisture-absorbing DMSO reduces solubility. Please use fresh DMSO.)

Water : Insoluble

Ethanol : Insoluble


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In vivo
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Tech Support

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