King-Díaz Beatriz, Macías-Ruvalcaba Norma A, Aguilar-Martínez Martha, Calaminici Patrizia, Köster Andreas M, Gómez-Sandoval Zeferino, Reveles J U, Lotina-Hennsen Blas
Departamento de Bioquímica, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, México, DF 04510, Mexico.
J Photochem Photobiol B. 2006 May 1;83(2):105-13. doi: 10.1016/j.jphotobiol.2005.11.012. Epub 2006 Feb 2.
Nineteen 2-[(R-phenyl)amine]-1,4-naphthalendione derivatives (PAN) were tested on spinach thylakoids for their activity as electron acceptors. These molecules act as photosystem I electron acceptors in the micromolar range. AC(50) values varied from 5 nM to 24 microM. QSAR analysis revealed a linear correlation of the m-PAN derivative log [1/AC(50)] with the energy difference of the LUMO and HOMO orbitals. The biological activity of p-PAN derivatives correlates linearly with structural parameters. Electron affinity is being the most important. The half wave I potential values (E(1/2)) of PAN compounds (from -213 to -569 mV vs. NHE) match with the mid-point potentials of the A(0) to F(X) niche of PSI electron transport carriers. The logP values of PAN derivatives were 3.35 and 3.88, indicating that they are hydrophobic compounds. Therefore PAN compounds accept electrons at the hydrophobic A(0) to F(X) niche of PSI.
对19种2-[(R-苯基)胺]-1,4-萘二酮衍生物（PAN）在菠菜类囊体上作为电子受体的活性进行了测试。这些分子在微摩尔范围内作为光系统I的电子受体。AC(50)值在5 nM至24 μM之间变化。定量构效关系（QSAR）分析表明，间位PAN衍生物的log [1/AC(50)]与最低未占分子轨道（LUMO）和最高已占分子轨道（HOMO）的能量差呈线性相关。对位PAN衍生物的生物活性与结构参数呈线性相关。电子亲和力是最重要的因素。PAN化合物的半波I电位值（E(1/2)，相对于标准氢电极（NHE）为-213至-569 mV）与光系统I电子传递载体从A(0)到F(X)位点的中点电位相匹配。PAN衍生物的logP值分别为3.35和3.88，表明它们是疏水化合物。因此，PAN化合物在光系统I的疏水A(0)到F(X)位点接受电子。
