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BODIPY Derivatives as Molecular Photoacoustic Contrast Agents Samir Laoui, 1 Seema Bag, 2 Olivier Dantiste, 1 Mathieu Frenette, 2 Maryam Hatamimoslehabadi,

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Presentation on theme: "BODIPY Derivatives as Molecular Photoacoustic Contrast Agents Samir Laoui, 1 Seema Bag, 2 Olivier Dantiste, 1 Mathieu Frenette, 2 Maryam Hatamimoslehabadi,"— Presentation transcript:

1 BODIPY Derivatives as Molecular Photoacoustic Contrast Agents Samir Laoui, 1 Seema Bag, 2 Olivier Dantiste, 1 Mathieu Frenette, 2 Maryam Hatamimoslehabadi, 1 Stephanie Bellinger-Buckley, 2 Jen-Chieh Tseng, 3 Jonathan Rochford, 2 Chandra Yelleswarapu 1 3 Lurie Family Imaging Center, Dana-Farber Cancer Institute, Boston, MA Department of Chemistry, 1 Department of Physics, University of Massachusetts Boston, Boston, MA This work is supported by UMass Boston and DF/HCC NIH U54 Minority Institution/Cancer Center Partnership Grant-1U54CA156732/4

2 Motivation Background Properties Bodipy derivatives PAZ-Scan Data Conclusion and future work Outline

3 Photoacoustic imaging/tomography (PAI) is an in vivo, non-ionizing imaging modality, that can provide location & metabolic activities of tumors with the help of contrast agents. To date, a variety of near-infrared (NIR) absorbing fluorophores, e.g. IRDye800CW, AlexaFluor 750 and ICG, have been used as exogenous contrast agents for deep tissue imaging. Such contrast agents were originally designed for fluorescent imaging applications and are thus optimized as such with a relatively poor photoacoustic response, their only redeeming feature being their excellent optical absorption in the biological transmission window of 600 – 1100 nm. Motivation

4 Background Jablonski diagram

5 Background - the photoacoustic effect The photoacoustic effect (conversion of light into sound) was published in 1880 by Alexander Graham Bell SOUND  LIGHT 

6 Strong light absorption (  max ) in biological transparent window ( nm) Large Stoke’s shift, dissipates excited state energy as heat (  H) via structural reorganization (  V)  A photoacoustic signal is basically a photoinduced heat + pressure wave Desired Physical Properties of MPACs

7 BODIPY Large  max, tunable max High Φ f How to re-direct excited state energy? = Fluorescence Quenching Strong light absorption (  max ) in biological transparent window ( nm) Small Stoke’s shift, very sharp excitation and emission peak, high fluorescence quantum yield. Desired Physical Properties of MPACs

8 Tuning of BODIPY Photophysics  = 0 Absorption spectra Emission spectra Fc-absorption spectra

9 Variations of BODIPY UV-vis (l max, nm) ε ( M -1 cm -1 ) fwhm ( cm -1 ) Emission (l max, nm) Φ Fl 1-BODIPY MeOPhBODIPY (MeOPh) 2 BODIPY FcBODIPY n/a 5-Fc 2 BODIPY Optical Characterization of BODIPY Derivatives

10 PAZ-scan Experiment

11 Nd:YAG Laser, 532 nm (or) OPO laser, nm 3 nsec pulse width Fiber probe to collect the fluorescence signal Ultrasound transducer to measure the photoacoustic signal Optical detector to measure the transmitted energy

12 PA and Optical Response of BODIPY

13 Both Linear and nonlinear absorption are occurring. PA and Optical Response of MeOPh-BODIPY

14 Both Linear and nonlinear absorption are occurring. PA and Optical Response of MeOPh 2 -BODIPY

15 PA and Optical Response of Fc 2 -BODIPY

16 PA Response of Fc and MEOH 2 -BODIPYs Reductive quenching mechanism

17 PA and Fluorescence of MeOH 2 -BODIPY Meoh 2 -BODIPY

18 Conclusion Successfully engineered a PA response from the BODIPY chromophores. Fluorescence quantum yield has been reduced from 0.9 to ~0 and the absorbed energy is channeled through non-radiative decay – increased in PA signal. Current work in progress is to move from using BODIPY derivatives to using Curcumin derivatives.

19 Dr. Jonathan Rochford Samir Laoui Dr. Maryam Hatamimoslehabadi Dr. Matthieu Fremette Stephanie Bellinger-Buckley U-54 The Graduate Student Association at Umass-Boston Acknowledgement

20 Thank you for your attention!


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