2-[(R-phenyl)amine]-1,4-naphthalendiones as photosystem I electron acceptors: structure-activity relationship of m- and p-PAN compounds with QSAR analysis.
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.
King-Díaz
Beatriz
B
Departamento de Bioquímica, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, México, DF 04510, Mexico.
Macías-Ruvalcaba
Norma A
NA
Aguilar-Martínez
Martha
M
Calaminici
Patrizia
P
Köster
Andreas M
AM
Gómez-Sandoval
Zeferino
Z
Reveles
J U
JU
Lotina-Hennsen
Blas
B
D000255:Adenosine Triphosphate / Q000096:biosynthesis; D004579:Electron Transport / Q000187:drug effects; D007536:Isomerism; D007700:Kinetics; D009285:Naphthoquinones / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D018462:Photobiology; D045331:Photosystem I Protein Complex / Q000187:drug effects* / Q000378:metabolism*; D021281:Quantitative Structure-Activity Relationship; D018724:Spinacia oleracea / Q000187:drug effects / Q000378:metabolism; D020524:Thylakoids / Q000187:drug effects / Q000378:metabolism
D009285:Naphthoquinones; D045331:Photosystem I Protein Complex; D000255:Adenosine Triphosphate