Efficient synthesis of novel near ir emitting distyrylboradiazaindacene sensitizers for photodynamic therapy

Dost, Zeynep
Photodynamic therapy (PDT) is a noninvasive method of treating malignant tumors and age-related macular degeneration. Current practice of PDT is limited to a few functionalized porphyrins, however these compounds are not considered to be ideal drugs for use in PDT. Among the limitations, the most prominent is the low extinction coefficient of porphyrins in the body’s therapeutic window. Therefore, there is a significant impetus to develop novel and better efficiency sensitizers for use in PDT. Boradiazaindacenes (BODIPY dyes or difluoroboradipyrrines) are well known fluorescent dyes. We discovered novel distyryl-derivatized boradiazaindacene dyes. These dyes have strong absorptions beyond 650nm. In order to transform these novel dyes into potential PDT reagents, bromine substituents were placed and then heavy atom effect was showed. We also demonstrated that on red-light excitation, singlet oxygen trap 1,3-diphenyl-iso-benzofuran is rapidly degraded.


Water soluble distyryl-boradiazaindacenes as efficient photosensitizers for photodynamic therapy
Atılgan, Serdar; Akkaya, Engin Umut; Department of Chemistry (2006)
Photodynamic therapy (PDT) is an emerging treatment modality for a range of disease classes, both cancerous and noncancerous. This has brought about an active pursiut of new PDT agents that can be optimized for the unique set of photophysical characteristics that are required for a succesful clinical agent. There are many reported or commercially available photosensitizers, but most have limitations, such as low photostability, or a limited usable range of solvent conditions. In this study, we introduced a ...
Chemoenzymatic synthesis of chiral hydroxymethyl cycloalkenols
Şenocak, Deniz; Demir, Ayhan Sıtkı; Department of Chemistry (2004)
Chiral cyclic alkenols with hydroxymethyl functionality are important structural units in many biologically active natural compouds such as prostaglandins, sesquiterpene antiviral agents, pentenomycins, xanthocidin, sarkomycin, etc. 1,3-cycloalkanediones are converted into bicyclic polyoxo derivatives with formaldehyde and trioxane in the presence of Lewis acid. Selective oxidation of the bicyclic compounds by using manganese(III)acetate followed by enzyme-catalyzed kinetic resolution afforded chiral bicycl...
Benzaldehyde lyase catalyzed synthesis of novel acyloins
Şimşek, İlke; Demir, Ayhan Sıtkı; Department of Chemistry (2009)
α-Hydroxy phosphonates are versatile building blocks for the synthesis of many biologically active compounds that display antiviral, antibacterial, anticancer, pesticide activities beside their enzyme inhibitory activities such as they are the inhibitors of rennin or human immunodeficiency virus (HIV) protease and polymerase. Benzaldehyde lyase is able to catalyze not only C-C bond formation reactions but also C-C bond breaking reactions with high enantioselectivity that brings about the development of new ...
Characterization of Novel O-Glycans Isolated from Tear and Saliva of Ocular Rosacea Patients
Özcan Kabasakal, Süreyya; Vieira, Ana C.; Park, Gun Wook; Kim, Jae Han; Mannis, Mark J.; Lebrilla, Carlito B. (American Chemical Society (ACS), 2013-03-01)
O-Glycans in saliva and tear isolated from patients suffering from ocular rosacea, a form of inflammatory ocular surface disease, were profiled, and their structures were elucidated using high resolution mass spectrometry. We have previously shown that certain structures, particularly sulfated oligosaccharides, increased in the tear and saliva of rosacea patients In this study, the structures of these glycans were elucidated using primarily tandem mass spectrometry. There were important similarities in the ...
Zora, Metin (American Chemical Society (ACS), 1994-02-25)
Reaction of chromium carbene complexes and 1-alkynylcyclobutenols leads to 2-alkenyl-4-cyclopentene-1,3-diones. Initial allkyne insertion affords a highly electrophilic carbene complex, which then undergoes an alkyl shift-ring expansion, ultimately producing 2-alkenyl-4-cyclopentene-1,3-diones.
Citation Formats
Z. Dost, “Efficient synthesis of novel near ir emitting distyrylboradiazaindacene sensitizers for photodynamic therapy,” M.S. - Master of Science, Middle East Technical University, 2006.