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Evaluation of PI polyamide conjugates with eight-base pair recognition and improvement of the aqueous solubility by PEGylation.

Abstract：

:To investigate the effect of elongating base-pair (bp) recognition sequences, we synthesized N-methylpyrrole-N-methylimidazole (PI) polyamide conjugates with eight-bp recognition (3-5). The DNA alkylating activities of conjugates 3-5 were evaluated by high-resolution denaturing polyacrylamide gel electrophoresis with a 208-bp DNA fragment. Conjugates 3-5 showed high alkylating activities at nanomolar concentrations. We then addressed the following issue about PI conjugates. Generally, PI polyamide conjugates hardly dissolve in aqueous solution. To improve the aqueous solubility, by the introduction of hydrophilic groups, we synthesized PI polyamide conjugates that were modified with a seco-CBI moiety (6-11). Conjugates 9-11 that were modified by methoxypolyethylene glycol (PEG) 750 acquired moderate solubility and stability in aqueous solution. In addition, conjugates 10 and 11 had high cytotoxicity against A549 and DU145.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Takagaki T,Bando T,Kitano M,Hashiya K,Kashiwazaki G,Sugiyama H

doi

10.1016/j.bmc.2011.08.009

subject

Has Abstract

pub_date

2011-10-01 00:00:00

pages

5896-902

issue

19

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(11)00633-X

journal_volume

19

pub_type

杂志文章

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