메뉴 건너뛰기




Volumn 16, Issue 7, 2010, Pages 2054-2062

Effect of the ortho modification of azobenzene on the photoregulatory efficiency of DNA hybridization and the thermal stability of its eis form

Author keywords

DNA; Intercalations; Isomerization; Modified azobenzenes; Photoswitches

Indexed keywords

AZO BOND; BASE PAIRS; BENZENE RING; CARBOXYL GROUPS; CIS-TO-TRANS ISOMERIZATION; COMPUTER MODELING; DNA DUPLEXES; DNA HYBRIDIZATION; DNA INTERCALATIONS; IMINO PROTONS; INVERSION PROCESS; LONE PAIR ELECTRONS; METHYL GROUP; NITROGEN ATOM; NMR SPECTROSCOPIC ANALYSIS; ORTHO POSITION; PHOTOREGULATION; PHOTOSWITCHES; SOLVENT EFFECTS; STACKING INTERACTION; STERIC HINDRANCES; THERMAL STABILITY; TRANS-CIS ISOMERIZATION;

EID: 76449119066     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902789     Document Type: Article
Times cited : (59)

References (43)
  • 1
    • 2442521507 scopus 로고    scopus 로고
    • and references therein.
    • Y. Ito, E. Fukusaki, J. Mol. Catal. B 2004, 28, 155-166, and references therein.
    • (2004) J. Mol. Catal. B , vol.28 , pp. 155-166
    • Ito, Y.1    Fukusaki, E.2
  • 7
    • 33746734322 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 4900-4921;
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 4900-4921
  • 8
    • 0036169162 scopus 로고    scopus 로고
    • and references therein.
    • f) C. J. Leumann, Bioorg. Med. Chem. 2002, 10, 841-854, and references therein.
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 841-854
    • Leumann, C.J.1
  • 19
    • 49249088339 scopus 로고    scopus 로고
    • Modification at the para position led to the reversed photoswitch with the combination of L-threoninol, see
    • Modification at the para position led to the reversed photoswitch with the combination of L-threoninol, see X. G. Liang, N. Takenaka, H. Nishioka, H. Asanuma, Chem. Asian J. 2008, 3, 553-560.
    • (2008) Chem. Asian J. , vol.3 , pp. 553-560
    • Liang, X.G.1    Takenaka, N.2    Nishioka, H.3    Asanuma, H.4
  • 24
    • 47849095157 scopus 로고    scopus 로고
    • and references therein.
    • b) S. Yagai, A. Kitamura, Chem. Soc. Rev. 2008, 37, 1520-1529, and references therein.
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1520-1529
    • Yagai, S.1    Kitamura, A.2
  • 28
    • 37049069409 scopus 로고
    • We did not synthesize tri- or tetramethylated azobenzenes because of the following reasons: Synthesis of tri- or tetraalkylated azobenzenes at ortho positions is rather difficult due to the steric hindrance between the methyl groups on both sides of the benzene rings note
    • We did not synthesize tri- or tetramethylated azobenzenes because of the following reasons: Synthesis of tri- or tetraalkylated azobenzenes at ortho positions is rather difficult due to the steric hindrance between the methyl groups on both sides of the benzene rings (C. J. Byrne, D. A. R. Happer, M. P. Hartshorn, H. K. J. Powell, J. Chem. Soc, Perkin Trans. 1 1987, 1649-1653). According to the literature (ref. [9b]), tri- or tetraalkylation at the ortho positions makes the trans-to-cis photoisomerization slower, and accordingly the cis content after UV light irradiation becomes much less, which is unfavorable for the efficient photoregulation. In addition, we think that fur- ther methylation might not improve the photoregulatory efficiency based on our present finding; modification of the distal benzene ring, but not the proximal one was effective for the significant improvement of photoregulatory efficiency.
    • (1987) J. Chem. Soc, Perkin Trans , vol.1 , pp. 1649-1653
    • Byrne, C.J.1    Happer, D.A.R.2    Hartshorn, M.P.3    Powell, H.K.J.4
  • 29
    • 76449087700 scopus 로고    scopus 로고
    • m curves were depicted in Figure S1 in the Supporting Information
    • m curves were depicted in Figure S1 in the Supporting Information.
  • 31
    • 76449109759 scopus 로고    scopus 로고
    • Our group previously also investigated the sequence dependency of non-modified Azo to obtain the nearest-neighbor parameter note
    • m on the adjacent base pair as that of 2′,6′-Me-Azo in both the trans and cis forms. In addition, although the length of the present sequence involving 2′,6′-MeAzo was four bases longer than that of Azo, which our group previously used, the ΔTm of 2′,6′-Me-Azo was higher than that of Azo in all the sequences, demonstrating the superiority of 2′,6′-Me-Azo (see the Supporting Information, Figure S2 and Table Sl).
    • (2005) Nucleic Acids Symp. Ser. , vol.49 , pp. 283-284
    • Asanuma, H.1    Matsunaga, D.2    Komiyama, M.3
  • 32
    • 76449088935 scopus 로고    scopus 로고
    • 9). Other terminal imino proton signals might be overlapped with the signal at δ = 12.8 ppm
    • 9). Other terminal imino proton signals might be overlapped with the signal at δ = 12.8 ppm.
  • 34
    • 76449119160 scopus 로고    scopus 로고
    • As described above, the DNA duplex that contain cis-2′,6′-Me- Azo was much more unstable than that of trans form.
    • As described above, the DNA duplex that contain cis-2′,6′-Me- Azo was much more unstable than that of trans form.
  • 36
    • 76449110165 scopus 로고    scopus 로고
    • Typical UV/Vis spectra of the thermal cis-to-trans isomerization are depicted in Figure S3 in the Supporting Information.
    • Typical UV/Vis spectra of the thermal cis-to-trans isomerization are depicted in Figure S3 in the Supporting Information.
  • 43
    • 76449116667 scopus 로고    scopus 로고
    • a of benzoic acid. But neither 2′,6′-Me-Azo nor 2,6-Me-Azo would dissolve at all under stronger acidic conditions.
    • a of benzoic acid. But neither 2′,6′-Me-Azo nor 2,6-Me-Azo would dissolve at all under stronger acidic conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.