More Radical Magic with B₁₂: B₁₂‐Catalyzed, Light‐Induced Cleavage of DNA

Abstract

B(12) in a new light: the B(12) derivative hydroxocobalamin can be used as an efficient catalyst for light-induced strand cleavage of DNA. The proposed radical process involves hydroxy radicals and is controlled by visible light. Such light-controlled radical reactions promise to be particularly useful in intracellular applications.

Phenylethynylcobalamin: A Light‐Stable and Thermolysis‐Resistant Organometallic Vitamin B12 Derivative Prepared by Radical Synthesis

“…It may thus be of interest, to consider designing related, substituted alkynylcobalamins that would be expected to be more inert against proteolysis. Indeed, the procedure developed here for the synthesis of 3 uses the unique radical trapping capacity of cob(II)alamin (4), [10,26] and promises to provide a path for the efficient preparation of a range of alkynylcobalamins.…”

Recent trends in the development of vitamin B12derivatives for medicinal applications

“…Binding of the analogue to the protein results in an increase in fluorescence that allows determining the `on` and `off` rates of the binding event. 55, 168 Shell, Lawrence and co-workers reported on the use of hydroxoCbl as photocatalyst for the cleavage of supercoiled DNA to relaxed circular DNA (Figure 9). This observation is an important finding since IF represents the most selective of the three transporting proteins, thus suggesting again that the biological uptake of 5`-OH modified B 12 derivatives is not affected by this structural modification.…”

Phenylethinylcobalamin: ein radikalsynthetisch hergestelltes, lichtstabiles und hitzeresistentes metallorganisches B12‐Derivat

“…[10,25] Wie anhand der bekannten Daten aus Kristallstrukturen der beiden B 12 -Bindeproteine (Übersicht in Lit. [7]) angenommen, hatten diese für das metallorganische B 12 [10,26] und verspricht, ein allgemeiner Weg für die effiziente Herstellung einer Reihe von Alkinylcobalaminen zu sein.…”