9-Acridinylpeptides and 9-acridinyl-4-nitrophenylsulfonylpeptides. Synthesis, binding to DNA, and photoinduced DNA cleavage

G Karup; O Buchardt; Peter E. Nielsen

9-Acridinylpeptides and 9-acridinyl-4-nitrophenylsulfonylpeptides. Synthesis, binding to DNA, and photoinduced DNA cleavage

12 Citations (Scopus)

Abstract

The preparation of 6-(9-acridinylamino)hexanoic acid DHBT ester and N alpha-Fmoc-N epsilon-(4-nitrophenylsulfonyl)-L-lysine DHBT ester and their application in solid phase peptide synthesis are described. The 9-acridinylamino ligand was shown to confer high DNA affinity, probably by intercalation, to the resulting peptides. The 4-nitrophenylsulfamido ligand furthermore resulted in "photonuclease" activity of some of the modified peptides.

Original language	English
Journal	International Journal of Peptide and Protein Research
Volume	32
Issue number	5
Pages (from-to)	331-43
Number of pages	13
ISSN	0367-8377
Publication status	Published - Nov 1988

Keywords

Acridines/chemical synthesis
Amino Acid Sequence
Chemical Phenomena
Chemistry
DNA/drug effects
Molecular Sequence Data
Molecular Structure
Nitrobenzenes/chemical synthesis
Peptides/chemical synthesis
Photochemistry
Sulfones/chemical synthesis

Cite this

@article{afc120d14de3456abc183e844bbaebaf,

title = "9-Acridinylpeptides and 9-acridinyl-4-nitrophenylsulfonylpeptides. Synthesis, binding to DNA, and photoinduced DNA cleavage",

abstract = "The preparation of 6-(9-acridinylamino)hexanoic acid DHBT ester and N alpha-Fmoc-N epsilon-(4-nitrophenylsulfonyl)-L-lysine DHBT ester and their application in solid phase peptide synthesis are described. The 9-acridinylamino ligand was shown to confer high DNA affinity, probably by intercalation, to the resulting peptides. The 4-nitrophenylsulfamido ligand furthermore resulted in {"}photonuclease{"} activity of some of the modified peptides.",

keywords = "Acridines/chemical synthesis, Amino Acid Sequence, Chemical Phenomena, Chemistry, DNA/drug effects, Molecular Sequence Data, Molecular Structure, Nitrobenzenes/chemical synthesis, Peptides/chemical synthesis, Photochemistry, Sulfones/chemical synthesis",

author = "G Karup and O Buchardt and Nielsen, {Peter E.}",

year = "1988",

month = nov,

language = "English",

volume = "32",

pages = "331--43",

journal = "International Journal of Peptide and Protein Research",

issn = "0367-8377",

publisher = "Wiley-Blackwell",

number = "5",

}

TY - JOUR

T1 - 9-Acridinylpeptides and 9-acridinyl-4-nitrophenylsulfonylpeptides. Synthesis, binding to DNA, and photoinduced DNA cleavage

AU - Karup, G

AU - Buchardt, O

AU - Nielsen, Peter E.

PY - 1988/11

Y1 - 1988/11

N2 - The preparation of 6-(9-acridinylamino)hexanoic acid DHBT ester and N alpha-Fmoc-N epsilon-(4-nitrophenylsulfonyl)-L-lysine DHBT ester and their application in solid phase peptide synthesis are described. The 9-acridinylamino ligand was shown to confer high DNA affinity, probably by intercalation, to the resulting peptides. The 4-nitrophenylsulfamido ligand furthermore resulted in "photonuclease" activity of some of the modified peptides.

AB - The preparation of 6-(9-acridinylamino)hexanoic acid DHBT ester and N alpha-Fmoc-N epsilon-(4-nitrophenylsulfonyl)-L-lysine DHBT ester and their application in solid phase peptide synthesis are described. The 9-acridinylamino ligand was shown to confer high DNA affinity, probably by intercalation, to the resulting peptides. The 4-nitrophenylsulfamido ligand furthermore resulted in "photonuclease" activity of some of the modified peptides.

KW - Acridines/chemical synthesis

KW - Amino Acid Sequence

KW - Chemical Phenomena

KW - Chemistry

KW - DNA/drug effects

KW - Molecular Sequence Data

KW - Molecular Structure

KW - Nitrobenzenes/chemical synthesis

KW - Peptides/chemical synthesis

KW - Photochemistry

KW - Sulfones/chemical synthesis

M3 - Journal article

C2 - 3209353

SN - 0367-8377

VL - 32

SP - 331

EP - 343

JO - International Journal of Peptide and Protein Research

JF - International Journal of Peptide and Protein Research

IS - 5

ER -

9-Acridinylpeptides and 9-acridinyl-4-nitrophenylsulfonylpeptides. Synthesis, binding to DNA, and photoinduced DNA cleavage

Abstract

Keywords

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