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 The leading web portal for pharmacy resources, news, education and careers March 20, 2019
Pharmacy Choice - Pharmaceutical News - Data from National Cancer Institute Advance Knowledge in Drug Delivery Systems (Harnessing Cyanine Reactivity for Optical Imaging and Drug Delivery) - March 20, 2019

Pharmacy News Article

 1/10/19 - Data from National Cancer Institute Advance Knowledge in Drug Delivery Systems (Harnessing Cyanine Reactivity for Optical Imaging and Drug Delivery)

By a News Reporter-Staff News Editor at Chemicals & Chemistry Current study results on Drugs and Therapies - Drug Delivery Systems have been published. According to news reporting originating in Frederick, Maryland, by VerticalNews journalists, research stated, "Optical approaches that visualize and manipulate biological processes have transformed modern biomedical research. An enduring challenge is to translate these powerful methods into increasingly complex physiological settings."

The news reporters obtained a quote from the research from National Cancer Institute, "Longer wavelengths, typically in the near-infrared (NIR) range (similar to 650-900 nm), can enable advances in both fundamental and clinical settings; however, suitable probe molecules are needed. The pentamethine and heptamethine cyanines, led by prototypes Cy5 and Cy7, are among the most useful compounds for fluorescence-based applications, finding broad use in a range of contexts. The defining chemical feature of these molecules, and the key chromophoric element, is an odd-numbered polymethine that links two nitrogen atoms. Not only a light-harvesting functional group, the cyanine chromophore is subject to thermal and photochemical reactions that dramatically alter many properties of these molecules. This Account describes our recent studies to define and use intrinsic cyanine chromophore reactivity. The hypothesis driving this research is that novel chemistries that manipulate the cyanine chromophore can be used to address challenging problems in the areas of imaging and drug delivery. We first review reaction discovery efforts that seek to address two limitations of long wavelength fluorophores: undesired thiol reactivity and modest fluorescence quantum yield. Heptamethine cyanines with an O-alkyl substituent at the central C4 ' carbon were prepared through a novel N- to O-transposition reaction. Unlike commonly used C4 '-phenol variants, this new class of fluorophores is resistant to thiol modification and exhibits improved in vivo imaging properties when used as antibody tags. We have also developed a chemical strategy to enhance the quantum yield of far-red pentamethine cyanines. Using a synthetic strategy involving a cross metathesis/tetracyclization sequence, this approach conformationally restrains the pentamethine cyanine scaffold. The resulting molecules exhibit enhanced quantum yield (Phi(F) = 0.69 vs Phi(F) = 0.15). Furthermore, conformational restraint improves interconversion between reduced hydrocyanine and intact cyanine forms, which enables super resolution microscopy. This Account then highlights efforts to use cyanine photochemical reactivity for NIR photocaging. Our approach involves the deliberate use of cyanine photooxidation, a reaction previously only associated with photodegradation. The uncaging reaction sequence is initiated by photooxidative chromophore cleavage (using wavelengths of up to 780 nm), which prompts a C-N bond hydrolysis/cyclization sequence resulting in phenol liberation. This approach has been applied to generate the first NIRactivated antibody-drug conjugates. Tumor uptake can be monitored in vivo using NIR fluorescence, prior to uncaging with an external irradiation source. This NIR uncaging strategy can slow tumor progression and increase survival in a MDA-MB-468-luc mouse model."

According to the news reporters, the research concluded: "Broadly, the vantage point of cyanine reactivity is providing novel probe molecules with auspicious features for use in complex imaging and drug delivery settings."

For more information on this research see: Harnessing Cyanine Reactivity for Optical Imaging and Drug Delivery. Accounts of Chemical Research, 2018;51(12):3226-3235. Accounts of Chemical Research can be contacted at: Amer Chemical Soc, 1155 16TH St, NW, Washington, DC 20036, USA. (American Chemical Society - www.acs.org; Accounts of Chemical Research - www.pubs.acs.org/journal/achre4)

Our news correspondents report that additional information may be obtained by contacting M.J. Schnermann, National Cancer Institute, Chem Biol Lab, Center Canc Res, Frederick, MD 20850, United States. Additional authors for this research include R.R. Nani and A.P. Gorka.

(Our reports deliver fact-based news of research and discoveries from around the world.)



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