HQNO

Names

[ CAS No. ]:
341-88-8

[ Name ]:
HQNO

[Synonym ]:
HOQNO
2-Heptylquinolin-4-ol 1-oxide
2 heptyl 4 hydroxyquinoline 1 oxide
4-Quinolinol,2-heptyl-,1-oxide
2-heptyl-1-hydroxyquinolin-4-one
2-Heptyl-4-quinolinol 1-oxide
HQNO
4-Quinolinol, 2-heptyl-, 1-oxide
2-heptyl-4-hydroxyquinoline n-oxide

Biological Activity

[Description]:

HQNO, secreted by P. aeruginosa, is a potent electron transport chain inhibitor with a Kd of 64 nM for complex III[1]. HQNO is a potent inhibitor of mitochondrial NDH-2 in many species[2].

[Related Catalog]:

Research Areas >> Infection

[Target]

NDH-2[2]

[In Vitro]

HQNO is a potent inhibitor of mitochondrial type II NADH:quinone oxidoreductase (NDH-2) in many species, including Yarrowia lipolytica, S. cerevisiae, Gluconobacter oxydans, T. gondii, P. falciparum, and S. aureus. HQNO targets the Q-site of NDH-2[2]. HQNO concentrations are varied from 0 to 100 μM and 0 to 300 μM for wild-type (WT) and I379E C. thermarum NDH-2 variant, respectively to determine IC50 values. WT NDH-2 has an IC50 value of 10.5±1.3 μM HQNO in the presence of 400 μM Menadione (MD). In the presence of 50 μM MD, the IC50 value for HQNO decreases slightly to 7.3±1.2 μM and near complete inhibition (~15% residual activity) is observed with >50 μM HQNO. At 50 μM MD, HQNO inhibition is observed with an IC50 value of 54.3±1.2 μM[2].

[References]

[1]. N J Jacobs, et al. Evidence for Involvement of the Electron Transport System at a Late Step of Anaerobic Microbial Heme Synthesis. Biochim Biophys Acta. 1977 Jan 6;459(1):141-4.

[2]. Jessica Petri, et al. Structure of the NDH-2 - HQNO Inhibited Complex Provides Molecular Insight Into Quinone-Binding Site Inhibitors. Biochim Biophys Acta Bioenerg. 2018 Jul;1859(7):482-490.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
445.8±37.0 °C at 760 mmHg

[ Melting Point ]:
156-157ºC

[ Molecular Formula ]:
C₁₆H₂₁NO₂

[ Molecular Weight ]:
259.343

[ Flash Point ]:
223.4±26.5 °C

[ Exact Mass ]:
259.157227

[ PSA ]:
42.23000

[ LogP ]:
3.18

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.558

Safety Information

[ Hazard Codes ]:
Xi

[ RTECS ]:
VC5890000

[ HS Code ]:
2933499090

Customs

[ HS Code ]: 2933499090

[ Summary ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds

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