Cationic porphyrin-quinoxaline conjugate as a photochemically triggered novel cytotoxic agent.

Abstract

A novel cationic porphyrin-quinoxaline conjugate 8 was prepared in good yield by the coupling of activated quinoxaline carboxylic acid 5 with an appropriate aminoporphyrin. The UV-vis spectra of conjugate 8 with the addition of ctDNA shows substantial hypochromicity (39%) and a red shift (12 nm) in the Soret band indicating intercalation and self stacking along the surface. The binding constant of conjugate 8 with ctDNA was determined to be 1.26×10(6) M(-1). The porphyrin-quinoxaline conjugate 8 displayed enhanced photocytotoxicity (IC50=0.06 μM) when compared to TMPyP against A549 cancer cells.

• Authors: Dalip Kumar, K P Chandra Shekar, Bhupendra Mishra, Ryohsuke Kurihara, Maiko Ogura, Takeo Ito
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 23 Issue 11 Pg. 3221-4 (Jun 01 2013) ISSN: 1464-3405 [Electronic] England
• PMID: 23639546 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2013 Elsevier Ltd. All rights reserved.

Chemical References

• Antineoplastic Agents
• Cations
• Porphyrins
• Quinoxalines
• DNA
• calf thymus DNA

Topics

• Animals
• Antineoplastic Agents (chemical synthesis, chemistry, toxicity)
• Cations (chemistry)
• Cattle
• Cell Line, Tumor
• Cell Survival (drug effects)
• DNA (chemistry, metabolism)
• DNA Cleavage (drug effects)
• Humans
• Porphyrins (chemical synthesis, chemistry, toxicity)
• Quinoxalines (chemical synthesis, chemistry, toxicity)
• Spectrometry, Fluorescence
• Ultraviolet Rays