195191-90-3

Upstream product

• 619-45-4 4-methoxycarbonyl aniline 
• 195191-89-0 4-(5-Bromo-pentanoylamino)-benzoic acid methyl ester 

Downstream Products

• 64124-33-0 4-(5-Aminovalerylamino)benzoesaeure 
• 195191-92-5 4-[5-(Acridin-9-ylamino)-pentanoylamino]-benzoic acid 
• 195191-91-4 4-(5-azido-pentanoylamino)-benzoic acid 

Relevant academic research and scientific papers

Photochemical cleavage of duplex DNA by N-benzoyloxy-2-thiopyridone linked to 9-aminoacridine

Upon illumination N-aroyloxy-2-thiopyridones induce non-specific single-strand nicks in duplex DNA at micromolar concentrations.

Design, synthesis, and evaluation of N-aroyloxy-2-thiopyridones as DNA photocleaving reagents

N-Benzoyloxy-2-thiopyridone (12) was shown to induce single-strand nicks in duplex DNA upon irradiation with visible light (λ~350nm). This finding led to the design of a series of compounds, in which an acridinyl nucleus was covalently linked to the N-benzoyloxy-2-thiopyridone unit. These conjugates (15, 16, 17 and 18) were synthesized and evaluated as novel DNA photocleaving reagents. Optimal photocleaving activity was observed for conjugate 16, in which a flexible polymethylene spacer of 4 carbons was used to connect the aminoacridine entity to the thiopyridone. This compound was shown to cleave DNA at low μM concentrations and was approximately two-orders of magnitude more efficient than the parent N-benzoyloxy-2-thiopyridone (12). Furthermore, the DNA cleavage ladders induced by 16 and 12 were found to be identical and of no significant sequence selectivity. These data suggest that the N-aroyloxy-2-thiopyridones can be used for the design of new DNA photocleaving reagents with potential use as 'photofootprinting agents' or as 'site-directed photonucleases'. Copyright (C) 1999 Elsevier Science Ltd.