Olorunsogo O O, Malomo S O, Bababunmi E A
Biochem Pharmacol. 1985 Aug 15;34(16):2945-52. doi: 10.1016/0006-2952(85)90020-6.
The acidity and lipophilicity of the fluorinated arylalkylsulphonamides are determined by the nature of the substituents on their aromatic rings. Herbicidal and anti-inflammatory effects of these compounds appear to increase with their lipophilicity. According to Mitchell's chemiosmotic theory, lipophilic weak-acid uncoupling agents act by transporting protons across the inner mitochondrial membrane and thus destroying the proton-electrochemical potential gradient required for ATP synthesis and ion transport. 1:1:1-Trifluoro-N-[2-methyl-4-(phenylsulphonyl) phenyl]methanesulphonamide (Perfluidone), a pre- and post-emergence herbicide (at 20 microM concentration), in isolated rat-liver mitochondria caused (1) a 2-fold stimulation of metabolic state-4 respiration, (2) a reduction of respiratory control ratio (RCR) by at least 50%, (3) an enhancement of latent ATPase activity by 40%, (4) a significant passive swelling of mitochondria in 0.15 N NH4Cl(delta A520 = -0.46 +/- 0.003), (5) proton intrusion during state-4 respiration (356 ng H+/min/mg protein; ng H+/min/mg protein with 5 microM perfluidone), and (6) at least 100% stimulation of oligomycin-inhibited respiration. These profiles are qualitatively comparable with those of the classical lipophilic weak-acid uncoupler, carbonylcyanide-trifluoro-methoxyphenylene hydrazone (FCCP), which acts by promoting the electrogenic transport of H+ ions across mitochondrial membrane.
氟化芳基烷基磺酰胺的酸度和亲脂性由其芳香环上取代基的性质决定。这些化合物的除草和抗炎作用似乎随着亲脂性的增加而增强。根据米切尔的化学渗透理论，亲脂性弱酸解偶联剂的作用是将质子转运穿过线粒体内膜，从而破坏ATP合成和离子转运所需的质子电化学势梯度。1:1:1-三氟-N-[2-甲基-4-(苯基磺酰基)苯基]甲磺酰胺（氟草敏），一种苗前和苗后除草剂（浓度为20微摩尔），在分离的大鼠肝线粒体中引起：(1) 代谢状态4呼吸的2倍刺激；(2) 呼吸控制率（RCR）至少降低50%；(3) 潜在ATP酶活性增强40%；(4) 在0.15 N NH4Cl中，线粒体显著被动肿胀（ΔA520 = -0.46 ± 0.003）；(5) 状态4呼吸期间质子内流（356纳克H+/分钟/毫克蛋白质；5微摩尔氟草敏时为纳克H+/分钟/毫克蛋白质）；(6) 对寡霉素抑制的呼吸至少有100%的刺激。这些特征在质量上与经典亲脂性弱酸解偶联剂羰基氰化物-三氟甲氧基苯腙（FCCP）的特征相当，后者通过促进H+离子跨线粒体膜的生电转运起作用。
