Proflavine dichloride dihydrate (3,6-diaminoacridine dihydrochloride dihydrate)

Obendorf, S. Kay; Carrell, H. L.; Glusker, Jenny P.

doi:10.1107/s0567740874004985

Cited by 20 publications

(10 citation statements)

References 5 publications

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“…Analogous interaction modes were also reported for proflavine, [41] acridine orange [21,42] and acridine orange derivatives. [26,43] This study has shown that the bifunctional molecule D and its Zn II complex ([ZnD]) interact with double-stranded DNA, to form stable complexes.…”

Section: Discussionsupporting

confidence: 72%

Tuning the Activity of Zn(II) Complexes in DNA Cleavage: Clues for Design of New Efficient Metallo-Hydrolases

et al. 2008

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The hydrolytic ability toward plasmid DNA of a mononuclear and a binuclear Zn(II) complex with two macrocyclic ligands, containing respectively a phenanthroline (L1) and a dipyridine moiety (L2), was analyzed at different pH values and compared with their activity in bis( p-nitrophenyl)phosphate (BNPP) cleavage. Only the most nucleophilic species [ZnL1(OH)]+ and [Zn2L2(OH)2]2+, present in solution at alkaline pH values, are active in BNPP cleavage, and the dinuclear L2 complex is remarkably more active than the mononuclear L1 one. Circular dichroism and unwinding experiments show that both complexes interact with DNA in a nonintercalative mode. Experiments with supercoiled plasmid DNA show that both complexes can cleave DNA at neutral pH, where the L1 and L2 complexes display a similar reactivity. Conversely, the pH-dependence of their cleavage ability is remarkably different. The reactivity of the mononuclear complex, in fact, decreases with pH while that of the dinuclear one is enhanced at alkaline pH values. The efficiency of the two complexes in DNA cleavage at different pH values was elucidated by means of a quantum mechanics/molecular mechanics (QM/MM) study on the adducts between DNA and the different complexed species present in solution.

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Section: Discussionsupporting

confidence: 72%

Tuning the Activity of Zn(II) Complexes in DNA Cleavage: Clues for Design of New Efficient Metallo-Hydrolases

et al. 2008

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“…1). All metric data for the organic unit are consistent with the corresponding values found in homologous derivatives (Obendorf et al, 1974;Jones &Neidle, 1975 andAchari &Neidle, 1976) (Fig. 2).…”

Section: Sup-1supporting

confidence: 86%

“…For similar structures, see: Obendorf et al (1974); Jones & Neidle (1975); Achari & Neidle (1976). For related literature, see: Berceanu et al (2002); Diop et al (2002).…”

Section: Related Literaturementioning

confidence: 97%

3,6-Diaminoacridinium perchlorate

Varga¹,

Rus²,

Venter³

et al. 2007

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 297 K; mean (C-C) = 0.003 Å; R factor = 0.051; wR factor = 0.132; data-to-parameter ratio = 12.9.The structure of the title compound, C 13 H 12 N 3 + ÁClO 4 À , reveals a twofold axis through the ring N and para-C atoms; a twofold rotation axis also passes through the Cl atom. The structure of the organic fragment is similar to that of homologous heterocyclic systems. The organic cations and perchlorate anions self-assemble in the solid state through C-HÁ Á ÁO and N-HÁ Á ÁO hydrogen bonds, leading to a two-dimensional layer parallel to the (112) plane. The layers are stacked along the c axis through offsetinteractions between cations from different layers (the distance between the planes through two cations is 3.35 Å ), resulting in a three-dimensional supramolecular architecture. ExperimentalCrystal data C 13 H 12 N 3 + ÁClO 4 À M r = 309.71 Monoclinic, C2=c a = 15.122 (3) Å b = 13.477 (3) Å c = 6.6922 (13) Å = 101.21 (3) V = 1337.8 (5) Å 3 Z = 4 Mo K radiation = 0.31 mm À1 T = 297 (2) K 0.33 Â 0.29 Â 0.19 mm Data collection Bruker SMART APEX CCD areadetector diffractometer Absorption correction: multi-scan (SHELXTL; Bruker, 2001) T min = 0.906, T max = 0.934 7044 measured reflections 1378 independent reflections 1271 reflections with I > 2(I) R int = 0.034

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“…In the structure of the 1:2 complex between ApA and proflavin (Shieh et al, 1982), the two proflavin cations are stacked almost directly on top of one another without the pronounced sliding seen in Figure 5 (top). The structure of proflavin dichloride (Obendorf et al, 1974) presents a somewhat related stacking geometry between two proflavin molecules with the two proflavin molecules parallel and with a rotation of 180°between each proflavin. The sandwiched proflavin molecules have a more pronounced stacking with the cytosine nucleotides of the first and last base pairs of the symmetrically related tetranucleotide molecules between which they are located (Figure 4).…”

Section: Resultsmentioning

confidence: 99%

Nonintercalative binding of proflavin to Z-DNA: structure of a complex between d(5BrC-G-5BrC-G) and proflavin

Westhof¹,

Hosur²,

Sundaralingam³

1988

Biochemistry

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The crystal structure of a disordered 1:1 complex between the tetradeoxyoligomer d(5BrC-G-5BrC-G) and proflavin has been determined and refined to an R factor of 26.9% for 474 reflections initially in space group P6(5) and to an R factor of 22.2% for 475 reflections in space group P2(1), both at 2-A resolution with Fobsd greater than or equal to 4.0. The unit cell constants are a = b = 17.9 A, c = 44.5 A, and gamma = 120 degrees. The final models are essentially the same in the two space groups with greater disorder in space group P6(5). In space group P2(1), the asymmetric unit is a tetranucleotide duplex, two sandwiched proflavin molecules, and four "outside-bound" proflavins. The tetranucleotide duplex is in the Z conformation and is located at the origin of the unit cell with a pair of proflavins sandwiched between the tetranucleotides. Thus, the tetranucleotides and proflavin dimers stack alternatively forming a quasi-continuous helix with the helix axis coincident with the c axis. The structure analysis revealed the presence of outside-bound proflavins as well. It is interesting that one type of outside-bound proflavins occupies a similar environment as the cobalt hexaammines in their complex with the decadeoxyoligomer d(CGTACGTACG) [Brennan, R. G., Westhof, E., & Sundaralingam, M. (1986) J. Biomol. Struct. Dyn. 3, 649]. Crystals of the latter are isomorphous to the present complex. The outside-bound proflavins penetrate the deep minor groove, thereby closing it off, and provide a visualization of a quasi-internal mode of binding of proflavin to a nucleic acid.

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Proflavine dichloride dihydrate (3,6-diaminoacridine dihydrochloride dihydrate)

Cited by 20 publications

References 5 publications

Tuning the Activity of Zn(II) Complexes in DNA Cleavage: Clues for Design of New Efficient Metallo-Hydrolases

Tuning the Activity of Zn(II) Complexes in DNA Cleavage: Clues for Design of New Efficient Metallo-Hydrolases

3,6-Diaminoacridinium perchlorate

Nonintercalative binding of proflavin to Z-DNA: structure of a complex between d(5BrC-G-5BrC-G) and proflavin

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