Synonym
NQ-301; NQ 301; NQ301.
IUPAC/Chemical Name
2-[(4-Acetylphenyl)amino]-3-chloro-1,4-naphthalenedione
InChi Key
LSQZKIQSQHZVQS-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H12ClNO3/c1-10(21)11-6-8-12(9-7-11)20-16-15(19)17(22)13-4-2-3-5-14(13)18(16)23/h2-9,20H,1H3
SMILES Code
O=C1C(NC2=CC=C(C(C)=O)C=C2)=C(Cl)C(C3=C1C=CC=C3)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
1: Jin YR, Cho MR, Lee KS, Lee JJ, Lim Y, Han XH, Oh KW, Hong JT, Yoo HS, Yun YP.
An antithrombotic agent, NQ301, inhibits thromboxane A2 receptor and synthase
activity in rabbit platelets. Basic Clin Pharmacol Toxicol. 2005 Sep;97(3):162-7.
PubMed PMID: 16128910.
2: Zhang YH, Chung KH, Ryu CK, Ko MH, Lee MK, Yun YP. Antiplatelet effect of
2-chloro-3-(4-acetophenyl)-amino-1,4-naphthoquinone (NQ301): a possible mechanism
through inhibition of intracellular Ca2+ mobilization. Biol Pharm Bull. 2001
Jun;24(6):618-22. PubMed PMID: 11411547.
3: Kang WS, Ryu CK, Chung KH, Ko MW, Joo JC, Yuk DY, Yoo HS, Yun YP. Antiplatelet
and antithrombotic activities of NQ301,
2-chloro-3-(4-acetophenyl)-amino-1,4-naphthoquinone. Biol Pharm Bull. 1999
Dec;22(12):1284-7. PubMed PMID: 10746156.
Biological target:
NQ301 is an antithrombotic agent with an IC50 of 10 mg/mL.
In vitro activity:
In the present study, the effect of NQ301 on arachidonic acid cascade in activated platelets has been examined. NQ301 concentrationdependently inhibited washed rabbit platelet aggregation induced by collagen (10 μg/ml), arachidonic acid (100 μM) and U46619 (1 μM), a thromboxane A2 receptor agonist, with IC50 values of 0.60±0.02, 0.78±0.04 and 0.58±0.04 μM, respectively. NQ301 also produced a shift to the right of the concentration-effect curve of U46619, indicating a competitive type of antagonism on thromboxane A2/prostaglandin H2 receptor. NQ301 slightly inhibited collagen-induced arachidonic acid liberation. In addition, NQ301 potently suppressed thromboxane B2 formation by platelets that were exposed to arachidonic acid in a concentration-dependent manner, but had no effect on the production of prostaglandin D2, indicating an inhibitory effect on thromboxane A2 synthase. This was supported by thromboxane A2 synthase activity assay that NQ301 concentration-dependently inhibited thromboxane B2 formation converted from prostaglandin H2. Moreover, NQ301 concentration-dependently inhibited 12-hydroxy-5,8,10,14-eicosatetraenoic acid formation by platelets that were exposed to arachidonic acid. Taken together, these results suggest that NQ301 has a potential to inhibit thromboxane A2 synthase activity with thromboxane A2/prostaglandin H2 receptor blockade, and modulate arachidonic acid liberation as well as 12-hydroxy-5,8,10,14-eicosatetraenoic acid formation in platelets.
Basic Clin Pharmacol Toxicol. 2005 Sep;97(3):162-7. https://pubmed.ncbi.nlm.nih.gov/16128910/
In vivo activity:
The antiplatelet and antithrombotic activities of a newly synthesized NQ301, 2-chloro-3-(4-acetophenyl)-amino-1,4-naphthoquinone, was investigated on human platelet aggregation in murine pulmonary thrombosis in vivo. NQ301 prevented death due to pulmonary thrombosis in mice dose-dependently in vivo. NQ301 also showed significant prolongation of tail bleeding time in conscious mice. These results suggest that NQ301 may be a promising antithrombotic agent, and the antithrombotic activity of NQ301 may be due to antiplatelet aggregation activity.
Biol Pharm Bull. 1999 Dec;22(12):1284-7. https://pubmed.ncbi.nlm.nih.gov/10746156/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
10.0 |
30.70 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
325.75
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Jin YR, Cho MR, Lee KS, Lee JJ, Lim Y, Han XH, Oh KW, Hong JT, Yoo HS, Yun YP. An antithrombotic agent, NQ301, inhibits thromboxane A2 receptor and synthase activity in rabbit platelets. Basic Clin Pharmacol Toxicol. 2005 Sep;97(3):162-7. doi: 10.1111/j.1742-7843.2005.pto_973123.x. PMID: 16128910. 2. Zhang YH, Chung KH, Ryu CK, Ko MH, Lee MK, Yun YP. Antiplatelet effect of 2-chloro-3-(4-acetophenyl)-amino-1,4naphthoquinone (NQ301): a possible mechanism through inhibition of intracellular Ca2+ mobilization. Biol Pharm Bull. 2001 Jun;24(6):618-22. doi: 10.1248/bpb.24.618. PMID: 11411547.
3. Kang WS, Ryu CK, Chung KH, Ko MW, Joo JC, Yuk DY, Yoo HS, Yun YP. Antiplatelet and antithrombotic activities of NQ301, 2-chloro-3-(4-acetophenyl)-amino-1,4-naphthoquinone. Biol Pharm Bull. 1999 Dec;22(12):1284-7. doi: 10.1248/bpb.22.1284. PMID: 10746156.
In vitro protocol:
1. Jin YR, Cho MR, Lee KS, Lee JJ, Lim Y, Han XH, Oh KW, Hong JT, Yoo HS, Yun YP. An antithrombotic agent, NQ301, inhibits thromboxane A2 receptor and synthase activity in rabbit platelets. Basic Clin Pharmacol Toxicol. 2005 Sep;97(3):162-7. doi: 10.1111/j.1742-7843.2005.pto_973123.x. PMID: 16128910. 2. Zhang YH, Chung KH, Ryu CK, Ko MH, Lee MK, Yun YP. Antiplatelet effect of 2-chloro-3-(4-acetophenyl)-amino-1,4naphthoquinone (NQ301): a possible mechanism through inhibition of intracellular Ca2+ mobilization. Biol Pharm Bull. 2001 Jun;24(6):618-22. doi: 10.1248/bpb.24.618. PMID: 11411547.
In vivo protocol:
1. Kang WS, Ryu CK, Chung KH, Ko MW, Joo JC, Yuk DY, Yoo HS, Yun YP. Antiplatelet and antithrombotic activities of NQ301, 2-chloro-3-(4-acetophenyl)-amino-1,4-naphthoquinone. Biol Pharm Bull. 1999 Dec;22(12):1284-7. doi: 10.1248/bpb.22.1284. PMID: 10746156.
1: Grebe T, Sarkari MT, Cherkaoui A, Schaumburg F. Exploration of compounds to
inhibit the Panton-Valentine leukocidin of Staphylococcus aureus. Med Microbiol
Immunol. 2024 Sep 19;213(1):19. doi: 10.1007/s00430-024-00803-1. PMID: 39297970;
PMCID: PMC11413081.
2: Kang WS, Ryu CK, Chung KH, Ko MW, Joo JC, Yuk DY, Yoo HS, Yun YP.
Antiplatelet and antithrombotic activities of NQ301,
2-chloro-3-(4-acetophenyl)-amino-1,4-naphthoquinone. Biol Pharm Bull. 1999
Dec;22(12):1284-7. doi: 10.1248/bpb.22.1284. PMID: 10746156.
3: Jin YR, Cho MR, Lee KS, Lee JJ, Lim Y, Han XH, Oh KW, Hong JT, Yoo HS, Yun
YP. An antithrombotic agent, NQ301, inhibits thromboxane A2 receptor and
synthase activity in rabbit platelets. Basic Clin Pharmacol Toxicol. 2005
Sep;97(3):162-7. doi: 10.1111/j.1742-7843.2005.pto_973123.x. PMID: 16128910.
4: Zhang YH, Chung KH, Ryu CK, Ko MH, Lee MK, Yun YP. Antiplatelet effect of
2-chloro-3-(4-acetophenyl)-amino-1,4-naphthoquinone (NQ301): a possible
mechanism through inhibition of intracellular Ca2+ mobilization. Biol Pharm
Bull. 2001 Jun;24(6):618-22. doi: 10.1248/bpb.24.618. PMID: 11411547.
