Porphyrins as spectroscopic sensors for conformational studies of DNA

被引:47
作者
Balaz, Milan [1 ]
Bitsch-Jensen, Klaus [1 ]
Mammana, Angela [1 ]
Ellestad, George A. [1 ]
Nakanishi, Koji [1 ]
Berova, Nina [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
porphyrins; circular dichroism; DNA conformation; DNA probe; B- to Z-DNA transition; oligonucleotides; DNA conjugates;
D O I
10.1351/pac200779040801
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Molecular systems containing two or more interacting porphyrins show remarkable spectroscopic features that allow for a very sensitive detection of conformational changes on the microscale level by different methods, such as fluorescence and electronic circular dichroism (ECD). Covalent porphyrin-DNA assemblies can provide a CD profile (exciton couplet) within the porphyrin Soret band region which is very diagnostic for DNA conformational changes. Additionally, covalently linked porphyrins have been shown to function as DNA molecular caps and to stabilize the non-self-complementary non-Watson-Crick guanine-adenine DNA sequence via their strong pi-pi stacking.
引用
收藏
页码:801 / 809
页数:9
相关论文
共 51 条
[1]  
Ardhammar M., 2000, CIRCULAR DICHROISM P, P741, DOI DOI 10.1021/AC802626E
[2]   Porphyrins conjugated to DNA as CD reporters of the salt-induced B to Z-DNA transition [J].
Balaz, M ;
Li, BC ;
Steinkruger, JD ;
Ellestad, GA ;
Nakanishi, K ;
Berova, N .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (10) :1865-1867
[3]   5′-Porphyrin-oligonucleotide conjugates:: Neutral porphyrin-DNA interactions [J].
Balaz, M ;
Steinkruger, JD ;
Ellestad, GA ;
Berova, N .
ORGANIC LETTERS, 2005, 7 (25) :5613-5616
[4]   Synthesis and circular dichroism of tetraarylporphyrin-oligonucleotide conjugates [J].
Balaz, M ;
Holmes, AE ;
Benedetti, M ;
Rodriguez, PC ;
Berova, N ;
Nakanishi, K ;
Proni, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) :4172-4173
[5]   A cationic zinc porphyrin as a chiroptical probe for Z-DNA [J].
Balaz, M ;
De Napoli, M ;
Holmes, AE ;
Mammana, A ;
Nakanishi, K ;
Berova, N ;
Purrello, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4006-4009
[6]   Porphyrin substituted phosphoramidites: new building blocks for porphyrin-oligonucleotide syntheses [J].
Balaz, M ;
Holmes, AE ;
Benedetti, M ;
Proni, G ;
Berova, N .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (07) :2413-2421
[7]   Tetraarylporphyrin as a selective molecular cap for non-Watson-Crick guanine-adenine base-pair sequences [J].
Balaz, Milan ;
Li, Benjamin C. ;
Jockusch, Steffen ;
Ellestad, George A. ;
Berova, Nina .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) :3530-3533
[8]   Nucleic acid conformation diversity: from structure to function and regulation [J].
Belmont, P ;
Constant, JF ;
Demeunynck, M .
CHEMICAL SOCIETY REVIEWS, 2001, 30 (01) :70-81
[9]   A porphyrin embedded in DNA [J].
Berlin, K ;
Jain, RK ;
Simon, MD ;
Richert, C .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1527-1535
[10]  
Berova, 2000, CIRCULAR DICHROISM P, P337