Structures of new DNA photocleaving agents: 3,6-bis(dimethylamino)-10- [6-(4-nitrobenzoyloxy)hexyl]acridinium chloride (I) and 9-([6-(4- nitrobenzoyloxy)-hexyl]amino)acridinium chloride monohydrate (II).
(I) C30H35N4O4+.Cl-, Mr = 551.07, triclinic, P1, a = 10.512 (2), b = 11.203 (2), c = 14.469 (2) A, alpha = 111.49 (1), beta = 105.74 (1), gamma = 95.82 (1) degrees, V = 1487.4 (4) A3, Z = 2, Dm = 1.23 (by flotation), Dx = 1.231 g cm-3, lambda(Cu K alpha) = 1.5418 A, mu = 14.68 cm-1, F(000) = 584, T = 296 K, R = 0.109 for 3100 unique reflections with I greater than 3 sigma(I). (II) C26H26N3O4+.Cl-.H2O, Mr = 497.98, triclinic, P1, a = 9.4810 (8), b = 14.495 (2), c = 9.255 (1) A, alpha = 95.48 (1), beta = 98.17 (1), gamma = 101.78 (1) degrees, V = 1222.3 (5) A3, Z = 2, Dm = 1.35 (by flotation), Dx = 1.353 g cm-3, lambda(Cu K alpha) = 1.5418 A, mu = 17.34 cm-1, F(000) = 524, T = 296 K, R = 0.052 for 3589 unique reflections with I greater than 3 sigma(I). The diffraction work confirmed the molecular structures of the newly synthesized DNA photocleaving compounds, in which the p-nitrophenyl group is nearly coplanar with the acridine moiety in (I), whereas the two planar groups form a dihedral angle of 98.7 degrees in (II). The flexibility of the methylene chain and the substantial stacking ability of the aromatic groups observed may be essential for binding to DNA and reaction with the deoxyribose H atoms.
Kuroda
R
R
Department of Chemistry, College of Arts and Sciences, University of Tokyo, Japan.
Shinomiya
M
M
D000609:Aminoacridines / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003460:Crystallization; D004247:DNA / Q000378:metabolism*; D015394:Molecular Structure; D009579:Nitrobenzoates / Q000737:chemistry*; D010777:Photochemistry; D011370:Proflavine / Q000031:analogs & derivatives* / Q000737:chemistry; D014466:Ultraviolet Rays; D014961:X-Ray Diffraction
D000609:Aminoacridines; D009579:Nitrobenzoates; C075328:3,6-bis(dimethylamino)-10-(6-(4-nitrobenzoyloxy)hexyl)acridinium; C075329:9-((6-(4-nitrobenzoyloxy)hexyl)amino)acridine; D004247:DNA; D011370:Proflavine