TY - JOUR
T1 - The synthesis of some indole-containing amino acids as linkers for the construction of DNA minor groove binders
AU - Khalaf, A.I.
AU - Pitt, A.R.
AU - Scobie, M.
AU - Suckling, C.J.
AU - Urwin, J.
AU - Waigh, R.D.
AU - Young, S.C.
AU - Fishleigh, R.V.
PY - 2000/6/1
Y1 - 2000/6/1
N2 - Molecular modelling studies showed that indole dicarboxylic acids are potential linkers for the synthesis of bis-netropsin analogues with a good fit to the minor groove of DNA. To test this hypothesis, 2-carboxyindole-6-acetic acid, indole-2,6-dicarboxylic acid, 6-(2-carboxyethyl)indole-2-carboxylic acid, 6-(2-carboxy-1-ethenyl)indole-2-carboxylic acid were prepared and coupled to 3-[1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido]dimethylaminopropane. Similarly indole-2,5-dicarboxylic acid was prepared and coupled to 3-[1-methyl-4-(1-methyl-4-aminopyrrple-2-carboxamido)pyrrole-2-carboxamido]propionamidine hydrochloride. The derivatives of 26-28 showed especially strong binding to AT rich regions as shown by footprinting studies.
AB - Molecular modelling studies showed that indole dicarboxylic acids are potential linkers for the synthesis of bis-netropsin analogues with a good fit to the minor groove of DNA. To test this hypothesis, 2-carboxyindole-6-acetic acid, indole-2,6-dicarboxylic acid, 6-(2-carboxyethyl)indole-2-carboxylic acid, 6-(2-carboxy-1-ethenyl)indole-2-carboxylic acid were prepared and coupled to 3-[1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido]dimethylaminopropane. Similarly indole-2,5-dicarboxylic acid was prepared and coupled to 3-[1-methyl-4-(1-methyl-4-aminopyrrple-2-carboxamido)pyrrole-2-carboxamido]propionamidine hydrochloride. The derivatives of 26-28 showed especially strong binding to AT rich regions as shown by footprinting studies.
KW - indole dicarboxylic acids
KW - synthesis DNA binding agents
KW - indole-containing analogues
KW - bis-netropsin
UR - http://openurl.ingenta.com/content?genre=article&issn=0308-2342&volume=2000&issue=6&spage=264&epage=265
M3 - Article
VL - 2000
SP - 264
EP - 265
JO - International Journal of Chemical Research
JF - International Journal of Chemical Research
SN - 0975-3699
IS - 6
ER -