Related Experiment Video
Updated: Mar 14, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Novel donor-π-acceptor benzimidazole-based chromophores: synthesis, antitumor assessment, and pharmacokinetics
Salhah D Al-Qahtani1, Ghadah M Al-Senani1, Khaled M Elattar2
1Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University P.O. Box 84428 Riyadh 11671 Saudi Arabia.
Abstract:
Targeted chromophores, 2-(N,N-dialkyl-/diaryl-aminophenyl)benzimidazole hybrids 2a, 2b, 4a, and 4b, were designed and synthesized. The designed hybrids were identified as donor-π-acceptor (D-π-A) structures, incorporating N,N-dialkyl/diarylamino groups as the donor moiety and nitro or pyridinyl Schiff-base groups as the acceptor moiety. The hybrids were found to exhibit significant solvent-dependent properties, especially in polar solvents such as DMSO, which enhanced their fluorescence properties. Conjugate 2a exhibited absorbance and fluorescence maxima at 390 and 528 nm, respectively, in DMSO, while hybrid 2b demonstrated absorbance and fluorescence maxima at 396 and 536 nm, respectively. Hybrids 4a and 4b exhibited similar solvent-dependent activity. The cytotoxicity of all the synthesized chromophores was tested against several human cancer cell lines using an MTT assay, and their inhibitory activity against VEGFR-2 was determined using an anti-phosphotyrosine-based quantitative kinase assay. Chromophore 4a exhibited the highest overall cytotoxicity, with IC50 = 12.64 ± 0.29 µM towards HepG2 cells and IC50 = 12.19 ± 0.30 µM towards PC3 cells. Meanwhile, the four targeted chromophores were tested towards VEGFR-2 using the reference sorafenib, which is a noticeable target in anti-angiogenic cancer therapy. The docking results revealed that hybrid 4b exhibited the strongest binding score, which was close to that of sorafenib (reference), suggesting that it shows the most promising profile. Analysis by SwissADME revealed that hybrids 2a and 4a exhibited good pharmacokinetic properties, such as high gastrointestinal absorption and blood-brain barrier permeability. In conclusion, the combined experimental and computational approach presented here suggests the potential of these benzimidazole chromophores as early leads for anticancer and anti-angiogenic agents.
More Related Videos
Related Concept Videos
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Adrenergic Agonists: Chemistry and Structure-Activity Relationship
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)