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BORDİPİRİN (BODIPY) BİLEŞİKLERİ KİMYASI VE UYGULAMALARI Engin Umut Akkaya Bilkent Üniversitesi, Kimya Bölümü & UMAM-Malzeme Bilimi ve Nanoteknoloji Enstitüsü.

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Presentation on theme: "BORDİPİRİN (BODIPY) BİLEŞİKLERİ KİMYASI VE UYGULAMALARI Engin Umut Akkaya Bilkent Üniversitesi, Kimya Bölümü & UMAM-Malzeme Bilimi ve Nanoteknoloji Enstitüsü."— Presentation transcript:

1 BORDİPİRİN (BODIPY) BİLEŞİKLERİ KİMYASI VE UYGULAMALARI Engin Umut Akkaya Bilkent Üniversitesi, Kimya Bölümü & UMAM-Malzeme Bilimi ve Nanoteknoloji Enstitüsü Ankara

2 Ion Sensing Photodynamic Therapy Solar Cells Molecular Logic Gates Energy Transfer Cassettes Liquid Crystals Light Harvesting systems DNA Labeling Bodipy: A versatile chromophore Bilkent University

3 Ziessel Boens Rurack & Daub Akkaya Burgess Derivatization of the BODIPY core Bilkent University Akkaya(2009)

4 Bilkent University Our First Encounter with Bodipy

5 Bilkent University Reverse PET/Bipyridyl-Bodipy

6 EET Moleküler Algılayıcısının Modüler Tasarımı Coşkun, A.; Akkaya, E. U. J. Am. Chem. Soc. 2005, 127,

7 Coskun, A.; Akkaya, E. U. J. Am. Chem. Soc., 2006, 128, Modulation of EET via cation binding Bilkent University

8 Hg Donör gruptan enerji aktarımının modülasyonu Guliyev, R.; Coskun, A.; Akkaya, E. U. J. Am. Chem. Soc., 2009, 131, 000.

9 Nanotechnology Takes Aim at Cancer Bilkent University

10 Dendrimers as versatile platforms Bilkent University

11 Oscar Raab/von Tappeiner (1900) A particular dye (acridine)+ Light, kills aquatic organisms. Jodlbauer/von Tappeiner (1904) “photodynamische wirkung” oxygen is also required for activity Meyer-Betz (1912) Demonstration of photodynamic activity in human. 200 mg hematoporphyrin (redness and oedema) Porphyria connection High concentration levels of protoporphyrin in plasma. FDA approval (1995) Photophyrin was approved for esophogal cancer. A very brief history of photodynamic therapy Bilkent University

12 Meyer-Betz: experiment on self

13 In December 1995, the FDA approved a photosensitizing agent called porfimer sodium (Photofrin) combined with light from a laser for treating patients with cancer of the esophagus in the following situations: To relieve symptoms of esophageal cancer, including difficulty swallowing, that are caused by a tumor obstructing (blocking) the esophagus To treat esophageal cancer that cannot be treated with laser therapy alone In 1998, the FDA approved porfimer sodium for two additional uses: To treat endobronchial (affecting the lining of the bronchi) non- small cell lung cancer that is microinvasive (has minimal spread of cancer cells) for patients who cannot have other types of treatment such as surgery or radiation therapy To reduce obstruction and to palliate (ease) symptoms in people with endobronchial non-small cell lung cancer that is either completely or partially obstructing the bronchi Practice of Photodyamic Therapy Bilkent University

14 From “Scientific American, January 2003* Bilkent University * New Light on Medicine

15 Bilkent University The Jablonski diagram

16 Light penetration in mammalian tissues Bilkent University

17 Enhanced permeation and retention- EPR Bilkent University

18 In vivo veritas ! Bilkent University

19 PDT: How the tumor dies Bilkent University

20 Potential Cancer Therapy – Endobronchial cancer – Esophageal cancer – Skin Cancers – Breast Cancers – Colorectal Tumors – Gynecologic malignancies Other Diseases – Cardiovascular (e.g., alternative to angioplasty) – Chronic skin diseases [e.g. Psoriasis (in development)] – Autoimmune (e.g. Rheumatoid arthritis) – Macular degeneration – Antibacterial (wound healing, oral cavity) – Vaccine – especially anticancer vaccines – Endometriosis – Precancerous conditions Applications of PDT Bilkent University

21 The light activated drugs in the market or in development Bilkent University

22 is a chemical compound that can be excited by light of a specific wavelength A good photosensitizer should have: Little or no toxicity in the dark Good pharmokinetic behaviour (high selectivity for tumour tissue and easy elimination from the body) A constant composition (preferably a single achiral substance) A high triplet quantum yield and a triplet energy with efficient energy transfer to produce singlet oxygen And red absorption to take advantage to deep light penetration Ideal photosensitizer for PDT Bilkent University

23 Quinone derivatives : Hypericin (590 nm), Acriflavin (460 nm). -Acridine dyes: Acridine Orange (492 nm) -Phenothiazine: Methylene blue (660 nm) -Xanthene dyes: Rose Bengal (549 nm) -Cyanine dyes: merocyanine (540 nm) -Porphyrins, Chlorins and Bacteriochlorin: Hematoporphyrin (645 nm) - Phthalocyanines: Phthalocyanine (698 nm), tetra-t-butylnaphthocyanine (784 nm) Dyes with known sensitizer activity Bilkent University

24 Red light activation of the sensitizer Bilkent University Filtered red light > 600 nm (2005)Red LED array = 625 nm (2006)

25 Boradiazaindacene based PDT reagents Bilkent University

26 TARGET PHOTOSENSITIZER Enhanced solubility in aqueous media The presence of heavy atoms provides enhanced intersystem crossing Long wavelength absorption ( nm)

27 Degradation of the singlet oxygen trap with 9 nM sensitizer Bilkent University

28 Percent viability as determined by a standard MTT assay. “Control” corresponds to assay data obtained with K562 cells kept in full medium in dark at 37 o C in an incubator. The other black bars show cell viability at different sensitizer concentrations in dark. Red bars show percent viability at the indicated concentrations under 4 hr irradiation with red LED at 2.5 mW/cm 2 fluence rate, followed by 20 hr incubation in dark at 37 o C. Percent viability values shown here are the averages of 4 runs. Standard MTT assay of photoinduced cytotoxicity Bilkent University


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