(E)-3-AP (Synonyms: (E)-PAN-811; (E)-NSC# 663249; (E)-OCX191)

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(E)-3-AP is the E configuration of 3-AP. 3-AP is a potent ribonucleotide reductase inhibitor. 3-AP shows anti-proliferative activity. 3-AP shows anticancer activity in L1210 leukemia model. 3-AP inhibits RR activity and DNA synthesis.

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(E)-3-AP Chemical Structure

CAS No. : 200933-27-3

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Other Forms of (E)-3-AP:

Triapine In-stock
Triapine hydrochloride Get quote

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Description

Cellular Effect

Cell Line	Type	Value	Description	References
A2780	IC₅₀	0.7 μM Compound: Triapine	Cytotoxicity against human A2780 cells incubated for 72 hrs by MTT assay Cytotoxicity against human A2780 cells incubated for 72 hrs by MTT assay	[PMID: 27336684]
A549	IC₅₀	2.288 μM Compound: 3-AP	Antiproliferative activity against human A549 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay Antiproliferative activity against human A549 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay	[PMID: 32438199]
BGC-823	IC₅₀	3.07 μM Compound: 3-AP	Antiproliferative activity against human BGC-823 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay Antiproliferative activity against human BGC-823 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay	[PMID: 32438199]
EC9706	IC₅₀	3.084 μM Compound: 3-AP	Antiproliferative activity against human EC9706 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay Antiproliferative activity against human EC9706 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay	[PMID: 32438199]
GES1	IC₅₀	5.4 μM Compound: 3-AP	Cytotoxicity against human GES-1 cells after 72 hrs by MTT assay Cytotoxicity against human GES-1 cells after 72 hrs by MTT assay	[PMID: 30108734]
GES1	IC₅₀	5.6 μM Compound: 3-AP	Antiproliferative activity against human GES-1 cells assessed as reduction in cell proliferation incubated for 72 hrs by MTT assay Antiproliferative activity against human GES-1 cells assessed as reduction in cell proliferation incubated for 72 hrs by MTT assay	[PMID: 31614257]
GES1	IC₅₀	6.103 μM Compound: 3-AP	Cytotoxicity against human GES1 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay Cytotoxicity against human GES1 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay	[PMID: 32438199]
HCT-116	IC₅₀	1.226 μM Compound: II	Dark cytotoxicity against human HCT116 cells expressing wild type p53 after 96 hrs by MTT assay Dark cytotoxicity against human HCT116 cells expressing wild type p53 after 96 hrs by MTT assay	[PMID: 24900837]
HGC-27	IC₅₀	11.495 μM Compound: 3-AP	Antiproliferative activity against human HGC-27 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay Antiproliferative activity against human HGC-27 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay	[PMID: 32438199]
HUVEC	IC₅₀	3448 nM Compound: 3-AP	Cytotoxicity against HUVEC assessed as reduction in cell viability incubated for 48 hrs by cell-titer-Glo luminescent cell viability assay Cytotoxicity against HUVEC assessed as reduction in cell viability incubated for 48 hrs by cell-titer-Glo luminescent cell viability assay	[PMID: 30835473]
KB 3-1	IC₅₀	> 800 μM Compound: 3-AP	Antiproliferative activity against human KB3-1 cells after 24 hrs by MTT assay Antiproliferative activity against human KB3-1 cells after 24 hrs by MTT assay	[PMID: 27524608]
KB 3-1	IC₅₀	> 800 μM Compound: 3-AP	Antiproliferative activity against human KB3-1 cells after 24 hrs in presence of P-gp inhibitor elacridar by MTT assay Antiproliferative activity against human KB3-1 cells after 24 hrs in presence of P-gp inhibitor elacridar by MTT assay	[PMID: 27524608]
KB 3-1	IC₅₀	1.4 μM Compound: 9	Cytotoxicity against human P-gp-negative KB-3-1 cells after 72 hrs by MTT assay Cytotoxicity against human P-gp-negative KB-3-1 cells after 72 hrs by MTT assay	[PMID: 19397322]
KB 3-1	IC₅₀	3.1 μM Compound: Triapine	Cytotoxicity against human KB-3-1 cells incubated for 72 hrs by MTT assay Cytotoxicity against human KB-3-1 cells incubated for 72 hrs by MTT assay	[PMID: 27336684]
KB-V1	IC₅₀	> 800 μM Compound: 3-AP	Antiproliferative activity against human KBV1 cells over expressing P-gp after 24 hrs by MTT assay Antiproliferative activity against human KBV1 cells over expressing P-gp after 24 hrs by MTT assay	[PMID: 27524608]
KB-V1	IC₅₀	> 800 μM Compound: 3-AP	Antiproliferative activity against human KBV1 cells over expressing P-gp after 24 hrs in presence of P-gp inhibitor elacridar by MTT assay Antiproliferative activity against human KBV1 cells over expressing P-gp after 24 hrs in presence of P-gp inhibitor elacridar by MTT assay	[PMID: 27524608]
KB-V1	IC₅₀	5.9 μM Compound: 9	Cytotoxicity against human P-glycoprotein-expressing KBV1 cells after 72 hrs by MTT assay Cytotoxicity against human P-glycoprotein-expressing KBV1 cells after 72 hrs by MTT assay	[PMID: 19397322]
L1210	IC₅₀	1.3 μM Compound: 1; 3-AP	Growth inhibition of mouse L1210 cells by MTS assay Growth inhibition of mouse L1210 cells by MTS assay	[PMID: 30904782]
MCF7	IC₅₀	> 32 μM Compound: 3-AP	Antiproliferative activity against human MCF7 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay Antiproliferative activity against human MCF7 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay	[PMID: 32438199]
MCF7	IC₅₀	18.85 μM Compound: 3-AP	Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay	[PMID: 30108734]
MES-SA	IC₅₀	1.305 μM Compound: Triapine	Cytotoxicity against human MES-SA cells transfected with mCherry fluorescent protein assessed as inhibition of cell proliferation incubated for 72 hrs by fluorescent assay Cytotoxicity against human MES-SA cells transfected with mCherry fluorescent protein assessed as inhibition of cell proliferation incubated for 72 hrs by fluorescent assay	[PMID: 27161177]
MES-SA/Dx5	IC₅₀	2.523 μM Compound: Triapine	Cytotoxicity against human MES-SA/DX5 cells transfected with mCherry fluorescent protein assessed as inhibition of cell proliferation incubated for 72 hrs by fluorescent assay Cytotoxicity against human MES-SA/DX5 cells transfected with mCherry fluorescent protein assessed as inhibition of cell proliferation incubated for 72 hrs by fluorescent assay	[PMID: 27161177]
MGC-803	IC₅₀	5.411 μM Compound: 3-AP	Antiproliferative activity against human MGC-803 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay Antiproliferative activity against human MGC-803 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay	[PMID: 32438199]
MGC-803	IC₅₀	9.68 μM Compound: 3-AP	Antiproliferative activity against human MGC803 cells after 72 hrs by MTT assay Antiproliferative activity against human MGC803 cells after 72 hrs by MTT assay	[PMID: 30108734]
MV4-11	IC₅₀	967.6 nM Compound: 3-AP	Antiproliferative activity against human MV4-11 cells assessed as reduction in cell viability incubated for 48 hrs by cell-titer-Glo luminescent cell viability assay Antiproliferative activity against human MV4-11 cells assessed as reduction in cell viability incubated for 48 hrs by cell-titer-Glo luminescent cell viability assay	[PMID: 30835473]
PC-3	IC₅₀	0.56 μM Compound: 3-AP	Antiproliferative activity against human PC-3 cells assessed as inhibition of cell proliferation measured after 72 hrs by MTT assay Antiproliferative activity against human PC-3 cells assessed as inhibition of cell proliferation measured after 72 hrs by MTT assay	[PMID: 33153765]
PC-3	IC₅₀	0.56 μM Compound: 3-AP	Antiproliferative activity against human PC3 cells assessed as reduction in cell proliferation incubated for 72 hrs by MTT assay Antiproliferative activity against human PC3 cells assessed as reduction in cell proliferation incubated for 72 hrs by MTT assay	[PMID: 31614257]
SGC-7901	IC₅₀	18.349 μM Compound: 3-AP	Antiproliferative activity against human SGC-7901 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay Antiproliferative activity against human SGC-7901 cells assessed as reduction in cell growth incubated for 72 hrs by MTT assay	[PMID: 32438199]
SK-N-MC	IC₅₀	0.26 μM Compound: 3-AP	Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay	[PMID: 19601577]
SK-N-MC	IC₅₀	0.26 μM Compound: 3-AP	Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay	[PMID: 17602603]
SK-N-MC	IC₅₀	0.31 μM Compound: triapine	Antiproliferative activity against human SK-N-MC cells by MTT assay Antiproliferative activity against human SK-N-MC cells by MTT assay	[PMID: 17142046]
SK-N-MC	IC₅₀	0.54 μM Compound: 3-AP	Antiproliferative activity against human SK-N-MC cells by MTT assay Antiproliferative activity against human SK-N-MC cells by MTT assay	[PMID: 17963372]
SMMC-7721	IC₅₀	42.81 μM Compound: 3-AP	Antiproliferative activity against human SMMC7721 cells after 72 hrs by MTT assay Antiproliferative activity against human SMMC7721 cells after 72 hrs by MTT assay	[PMID: 30108734]
SW480	IC₅₀	> 50 μM Compound: Triapine	Cytotoxicity against triapine-resistant human SW480 cells incubated for 72 hrs by MTT assay Cytotoxicity against triapine-resistant human SW480 cells incubated for 72 hrs by MTT assay	[PMID: 27336684]
SW480	IC₅₀	0.84 μM Compound: Triapine	Cytotoxicity against human SW480 cells incubated for 72 hrs by MTT assay Cytotoxicity against human SW480 cells incubated for 72 hrs by MTT assay	[PMID: 27336684]
WI-38	IC₅₀	> 25 μM Compound: Triapine	Cytotoxicity against human WI38 cells incubated for 72 hrs by MTT assay Cytotoxicity against human WI38 cells incubated for 72 hrs by MTT assay	[PMID: 27336684]

In Vitro

3-AP shows anti-proliferative activity with IC₅₀ values of 1.3, 1.6 µM for L1210, L1210/HUr cells, respectively^[1].
3-AP (5, 10, 15, 20, 30 mg/kg; i.p.; twice daily for six consecutive days) significantly increases in life span were observed with each dosage employed and long term survivors^[1].

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

Molecular Weight

195.24

Formula

C₇H₉N₅S

CAS No.

200933-27-3

SMILES

NC1=CC=CN=C1/C=N/NC(N)=S.[(E)]

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Finch RA, et al. Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone; 3-AP): an inhibitor of ribonucleotide reductase with antineoplastic activity. Adv Enzyme Regul. 1999;39:3-12. [Content Brief]

[2]. Enyedy ÉA ,et al. Complex formation and cytotoxicity of Triapine derivatives: a comparative solution study on the effect of the chalcogen atom and NH-methylation. Dalton Trans. 2020 Dec 8;49(46):16887-16902. [Content Brief]

(E)-3-AP Related Classifications

Molarity Calculator
Dilution Calculator

The molarity calculator equation

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

Mass		Concentration		Volume		Molecular Weight *
	=		×		×

The dilution calculator equation

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

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)	×	Volume _(start)	=	Concentration _(final)	×	Volume _(final)
	×		=		×
C1		V1		C2		V2

Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

(E)-3-AP200933-27-3(E)-PAN-811 (E)-NSC# 663249 (E)-OCX191DNA/RNA SynthesisL1210 leukemia cellsanti-proliferativeanticancerDNA synthesisInhibitorinhibitorinhibit

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