Three‐Arm, Biotin‐Tagged Carbazole–Dicyanovinyl–Chlorambucil Conjugate: Simultaneous Tumor Targeting, Sensing, and Photoresponsive Anticancer Drug Delivery

Abstract

The design, synthesis, and in vitro biological studies of a biotin-carbazole-dicyanovinyl-chlorambucil conjugate (Bio-CBZ-DCV-CBL; 6) are reported. This conjugate (6) is a multifunctional single-molecule appliance composed of a thiol-sensor DCV functionality, a CBZ-derived phototrigger as well as fluorescent reporter, and CBL as the anticancer drug, and Bio as the cancer-targeting ligand. In conjugate 6, the DCV bond undergoes a thiol-ene click reaction at pH<7 with intracellular thiols, thereby shutting down internal charge transfer between the donor CBZ and acceptor DCV units, resulting in a change of the fluorescence color from green to blue, and thereby, sensing the tumor microenvironment. Subsequent photoirradiation results in release of the anticancer drug CBL in a controlled manner.

A Noble‐Metal‐Free Heterogeneous Photosensitizer‐Relay Catalyst Triad That Catalyzes Water Oxidation under Visible Light

“…SSA graphs of the investigated compounds show typical characteristic of porphyrins,a ss hown in the Supporting Information, Figure S23. [37] FL measurements are given in the Supporting Information, Figures S24 and S25.…”

Dual-wavelength efficient two-photon photorelease of glycine by π-extended dipolar coumarins

“…Among the light-responsive organic structures available, uncagers1–3 represent key tools for biological and biomedical studies. These compounds act as photolabile protecting groups (PPGs) towards bioactive messengers, drugs4–6 or neurotransmitters,7–9 by masking their biological function. Suitable light irradiation then triggers the physiological response by releasing the free molecule with remarkable temporal and spatial control.…”

Bis‐Acetyl Carbazole: A Photoremovable Protecting Group for Sequential Release of Two Different Functional Groups and Its Application in Therapeutic Release

“…The limitations of utilizing the ANB chromophore in the area of drug release are (i) it requires UV light < 350 nm and (ii) is nonfluorescent in nature. Recently, our group presented acetyl carbazole as a fluorescent PRPG (FPRPG) for the dual release of the same type of functional group (carboxylic acids) , . Herein, we present bis‐acetyl carbazole as a FPRPG for the sequential release of two different functional groups such as carboxylic acids, alcohols, thiols, and amines on exposure to UV light ( λ ≥ 365 nm).…”