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Naphthalene diimide bis-guanidinio-carbonyl-pyrrole as a pH-switchable threading DNA intercalator
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2020-09-08 , DOI: 10.3762/bjoc.16.185
Poulami Jana , Filip Šupljika , Carsten Schmuck , Ivo Piantanida

A novel naphthalene diimde analogue (NDI) equipped at the imide positions with two guanidinio-carbonyl-pyrrole (GCP) pendant arms interacted significantly stronger with ds-DNA at pH 5 than at pH 7, due to reversible protonation of the GCP arms. This was consequence of a pH-switchable threading intercalation into ds-DNAs only at pH 5, while at neutral conditions (pH 7) NDI-GCP2 switched to the DNA minor groove binding. Intriguingly, NDI-GCP2 was at both pH values studied bound to the ds-RNA major groove, still showing a higher affinity and thermal denaturation effect at pH 5 due to GCP protonation. At excess over the DNA/RNA conjugate NDI-GCP2 showed also aggregation along the ds-polynucleotide and AFM and DLS demonstrated that NDI-GCP2 has pronounced ds-DNA condensation ability.

中文翻译:

萘二酰亚胺双胍基羰基吡咯作为pH值可转换的穿线DNA嵌入剂

一种新型的萘二酰亚胺类似物(NDI),在酰亚胺位置配备了两个胍基-羰基-吡咯(GCP)侧链,在pH 5时与ds-DNA相互作用比在pH 7时显着强,这是由于GCP臂的可逆质子化。这是仅在pH 5时,pH可调线程插入ds-DNA的结果,而在中性条件(pH 7)下,NDI-GCP 2转换为DNA小沟结合。有趣的是,NDI-GCP 2的两个pH值均与ds-RNA主沟结合,但由于GCP质子化,在pH 5时仍显示出更高的亲和力和热变性作用。超过DNA / RNA偶联物的NDI-GCP 2也沿ds-多核苷酸聚集,AFM和DLS证实NDI-GCP 2 具有明显的ds-DNA缩合能力。
更新日期:2020-09-08
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