A series of four 2‑amino‑3‑cyano‑4‑(3/4‑pyridyl)‑4H‑benzo[h]chromenes 2a–d and their dichlorido(p‑cymene)ruthenium(II) complexes 3a–d were tested for antiproliferative, vascular-disruptive, anti-angiogenic and DNA-binding activity. The coordination of the 4‑pyridyl‑4H‑naphthopyrans 2 to ruthenium led to complexes with pleiotropic effects. Unlike the free ligands 2a–d, their ruthenium complexes 3a–d showed a significant affinity for DNA as demonstrated by electrophoretic mobility shift assays (EMSA) and ethidium bromide assays. Binding of 3a–d to calf thymus DNA proceeded about 10-times faster compared with cisplatin. Treatment of HT-29 colon carcinoma, 518A2 melanoma and MCF-7^Topo breast cancer cells with 3a and 3b caused an accumulation of cells in the G2/M phase and an increase of the fraction of mitotic cells in the case of HT-29, due to alterations of the microtubule cytoskeleton as shown by immunofluorescence staining. Complexes 3b–c showed a dual effect on the vascular system. They suppressed angiogenesis in zebrafish embryos and they destroyed the vasculature of the chorioallantoic membrane (CAM) in fertilized chicken eggs. They also inhibited the vasculogenic mimicry, typical of U-87 glioblastoma cells in tube formation assays.

一系列4种2-氨基-3-氰基4-（3 / 4-吡啶基）-4 H-苯并[ h ]色酮2a - d和它们的二氯基（p- Cymene）钌（II）配合物3a - d为经测试具有抗增殖，破坏血管，抗血管生成和DNA结合的活性。4吡啶基4 H-萘并吡喃2与钌的配位导致复合物具有多效性效应。与游离配体2a – d不同，它们的钌络合物3a – d电泳迁移率变动分析（EMSA）和溴化乙锭分析显示出对DNA具有显着的亲和力。与顺铂相比，3a - d与小牛胸腺DNA的结合快约10倍。HT-29结肠癌，518A2黑素瘤和MCF-7的治疗^地形与乳腺癌细胞图3a和3b中引起细胞在G2 / M阶段中的积累和在HT-29的情况下的增加的有丝分裂细胞的比例的，如免疫荧光染色所示，由于微管细胞骨架的改变。配合物3b – c对血管系统显示出双重作用。他们抑制了斑马鱼胚胎中的血管生成，并破坏了受精卵中绒毛膜的血管系统。他们还抑制了血管生成模拟，这是在管形成实验中典型的U-87胶质母细胞瘤细胞。