title: Molecular size, shape, and electric charges: essential for perylene bisimide-based DNA intercalator to localize in cell nuclei and inhibit cancer cell growth.
abstract: The molecular properties concerning size, shape, and electric charges of the planar aromatic DNA intercalators are still poorly understood. Herein, a series of water-soluble perylene bisimide (PBI) derivatives containing a rigid and planar aromatic nanoscaffold with different size, shape, and electric charges were synthesized. Using histochemistry and cell viability assays on animal tissues and cancer cells, we revealed the molecular properties required for successful DNA intercalators to localize in cell nuclei and inhibit cancer cells. Small molecular size and the strong polarity of hydrophilic substituents are prerequisites for PBI-based DNA intercalators. A large number of charges facilitate the nucleic accumulation of these DNA intercalators, while fewer charges and planar aromatic nanoscaffold more efficiently inhibit cancer cell growth.
authors.affiliation: †State Key Laboratory of Chemical Resource Engineering, Key Laboratory of Carbon Fiber and Functional Polymers of Ministry of Education, Beijing Laboratory of Biomedical Materials, Beijing University of Chemical Technology, 100029 Beijing, China.
authors.forename: Zejun
authors.initials: Z
authors.lastname: Xu
authors.affiliation: †State Key Laboratory of Chemical Resource Engineering, Key Laboratory of Carbon Fiber and Functional Polymers of Ministry of Education, Beijing Laboratory of Biomedical Materials, Beijing University of Chemical Technology, 100029 Beijing, China.
authors.forename: Wenyu
authors.initials: W
authors.lastname: Cheng
authors.affiliation: ‡State Key Laboratory of Agrobiotechnology and College of Veterinary Medicine, China Agricultural University, 100193 Beijing, China.
authors.forename: Kunru
authors.initials: K
authors.lastname: Guo
authors.affiliation: ‡State Key Laboratory of Agrobiotechnology and College of Veterinary Medicine, China Agricultural University, 100193 Beijing, China.
authors.forename: Jieshi
authors.initials: J
authors.lastname: Yu
authors.affiliation: ‡State Key Laboratory of Agrobiotechnology and College of Veterinary Medicine, China Agricultural University, 100193 Beijing, China.
authors.forename: Jie
authors.initials: J
authors.lastname: Shen
authors.affiliation: ‡State Key Laboratory of Agrobiotechnology and College of Veterinary Medicine, China Agricultural University, 100193 Beijing, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Tang
authors.affiliation: †State Key Laboratory of Chemical Resource Engineering, Key Laboratory of Carbon Fiber and Functional Polymers of Ministry of Education, Beijing Laboratory of Biomedical Materials, Beijing University of Chemical Technology, 100029 Beijing, China.
authors.forename: Wantai
authors.initials: W
authors.lastname: Yang
authors.affiliation: †State Key Laboratory of Chemical Resource Engineering, Key Laboratory of Carbon Fiber and Functional Polymers of Ministry of Education, Beijing Laboratory of Biomedical Materials, Beijing University of Chemical Technology, 100029 Beijing, China.
authors.forename: Meizhen
authors.initials: M
authors.lastname: Yin
mesh_terms: D000818:Animals; D002417:Cattle; D045744:Cell Line, Tumor; D002467:Cell Nucleus / Q000378:metabolism*; D049109:Cell Proliferation; D002942:Circular Dichroism; D004247:DNA / Q000378:metabolism*; D004330:Drosophila / Q000378:metabolism; D004560:Electricity; D005453:Fluorescence; D006801:Humans; D007094:Imides / Q000138:chemical synthesis / Q000737:chemistry*; D007364:Intercalating Agents / Q000138:chemical synthesis / Q000737:chemistry*; D008970:Molecular Weight; D009369:Neoplasms / Q000473:pathology*; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D012469:Salivary Glands / Q000378:metabolism; D013050:Spectrometry, Fluorescence; D014783:Viscosity
chemical_list: D007094:Imides; D007364:Intercalating Agents; C510697:perylene bisimide; D010569:Perylene; D004247:DNA; C427203:calf thymus DNA
keywords: DNA intercalator; anticancer activity; cell imaging; nucleic accumulation; perylene bisimide; planar aromatic nanoscaffold