Naphthalene-fused BODIPY near-infrared dye as a stable contrast agent for in vivo photoacoustic imaging.

Photoacoustic imaging (PAI) has emerged as an advantageous modality with high resolution and deep tissue penetration. However, its application is limited by the lack of available contrast agents. In this work, we report the synthesis of a naphthalene fused BODIPY dimer Na-BD, and the impact of the electronic structure on the oxidative cyclo-dehydrogenation process was systematically studied. Na-BD exhibited intense NIR absorption, much better photo-stability and higher PA activity compared to commercial ICG dye, which makes it an excellent contrast agent for PAI. Moreover, the in vivo PAI studies based on Na-BD loaded BSA nanoparticles were carried out and they demonstrated a significant passive targeting capacity by exploiting the enhanced permeability and retention effect in the tumor region.

[1]  Yanglong Hou,et al.  Multifunctional Fe5C2 Nanoparticles: A Targeted Theranostic Platform for Magnetic Resonance Imaging and Photoacoustic Tomography‐Guided Photothermal Therapy , 2014, Advanced materials.

[2]  Stanislav Emelianov,et al.  Silver nanoplate contrast agents for in vivo molecular photoacoustic imaging. , 2012, ACS nano.

[3]  S. Gambhir,et al.  Light in and sound out: emerging translational strategies for photoacoustic imaging. , 2014, Cancer research.

[4]  Chris Jun Hui Ho,et al.  Multifunctional Photosensitizer-Based Contrast Agents for Photoacoustic Imaging , 2014, Scientific Reports.

[5]  Jishan Wu,et al.  Benzene-fused BODIPYs: synthesis and the impact of fusion mode. , 2013, Chemical Communications.

[6]  Nitish V. Thakor,et al.  Conjugated polymer nanoparticles for photoacoustic vascular imaging , 2014 .

[7]  G. Ulrich,et al.  Luminescent materials: locking π-conjugated and heterocyclic ligands with boron(III). , 2014, Angewandte Chemie.

[8]  Jesse V Jokerst,et al.  Photoacoustic imaging of mesenchymal stem cells in living mice via silica-coated gold nanorods. , 2012, ACS nano.

[9]  K. Kikuchi,et al.  BODIPY-based probes for the fluorescence imaging of biomolecules in living cells. , 2015, Chemical Society reviews.

[10]  Zhuang Liu,et al.  Drug delivery with carbon nanotubes for in vivo cancer treatment. , 2008, Cancer research.

[11]  Z. Duan,et al.  Biodistribution and Pharmacokinetic Analysis of Paclitaxel and Ceramide Administered in Multifunctional Polymer-Blend Nanoparticles in Drug Resistant Breast Cancer Model , 2008, Molecular pharmaceutics.

[12]  T. Hasan,et al.  Shining Light on the Dark Side of Imaging: Excited State Absorption Enhancement of a Bis-styryl BODIPY Photoacoustic Contrast Agent , 2014, Journal of the American Chemical Society.

[13]  A. Bell On the production and reproduction of sound by light , 1880, American Journal of Science.

[14]  Kuo‐Wei Huang,et al.  Perylene-fused BODIPY dye with near-IR absorption/emission and high photostability. , 2011, Organic letters.

[15]  Ben Zhong Tang,et al.  Biocompatible Nanoparticles with Aggregation‐Induced Emission Characteristics as Far‐Red/Near‐Infrared Fluorescent Bioprobes for In Vitro and In Vivo Imaging Applications , 2012 .

[16]  Zhichuan J. Xu,et al.  Synthesis, Functionalization, and Biomedical Applications of Multifunctional Magnetic Nanoparticles , 2010, Advanced materials.

[17]  Junjie Yao,et al.  Near-infrared optical-resolution photoacoustic microscopy. , 2014, Optics letters.

[18]  M. Dewhirst,et al.  Tumor vascular permeability, accumulation, and penetration of macromolecular drug carriers. , 2006, Journal of the National Cancer Institute.

[19]  Zhuang Liu,et al.  Carbon nanotubes as photoacoustic molecular imaging agents in living mice. , 2008, Nature nanotechnology.

[20]  Stanislav Emelianov,et al.  Indocyanine green-loaded photoacoustic nanodroplets: dual contrast nanoconstructs for enhanced photoacoustic and ultrasound imaging. , 2014, ACS nano.

[21]  Jesse V. Jokerst,et al.  Semiconducting Polymer Nanoparticles as Photoacoustic Molecular Imaging Probes in Living Mice , 2014, Nature nanotechnology.

[22]  Chulhong Kim,et al.  Porphyrin shell microbubbles with intrinsic ultrasound and photoacoustic properties. , 2012, Journal of the American Chemical Society.

[23]  V. Ntziachristos,et al.  Molecular imaging by means of multispectral optoacoustic tomography (MSOT). , 2010, Chemical reviews.

[24]  Jishan Wu,et al.  Far-red and near infrared BODIPY dyes: synthesis and applications for fluorescent pH probes and bio-imaging. , 2014, Organic & biomolecular chemistry.

[25]  Jinfeng Zhang,et al.  Aggregation-induced near-infrared absorption of squaraine dye in an albumin nanocomplex for photoacoustic tomography in vivo. , 2014, ACS applied materials & interfaces.

[26]  M. Ishii,et al.  In vivo fluorescence imaging of bone-resorbing osteoclasts. , 2011, Journal of the American Chemical Society.

[27]  Wei Huang,et al.  Perylene‐Diimide‐Based Nanoparticles as Highly Efficient Photoacoustic Agents for Deep Brain Tumor Imaging in Living Mice , 2015, Advanced materials.

[28]  Jishan Wu,et al.  Anthracene-fused BODIPYs as near-infrared dyes with high photostability. , 2011, Organic letters.

[29]  D. Ramaiah,et al.  Efficient reaction based colorimetric probe for sensitive detection, quantification, and on-site analysis of nitrite ions in natural water resources. , 2013, Analytical chemistry.

[30]  Younan Xia,et al.  Near-infrared gold nanocages as a new class of tracers for photoacoustic sentinel lymph node mapping on a rat model. , 2009, Nano letters.

[31]  Kevin Burgess,et al.  BODIPY dyes and their derivatives: syntheses and spectroscopic properties. , 2007, Chemical reviews.

[32]  S. Sakka,et al.  Assessing liver function , 2007, Current opinion in critical care.

[33]  Hao Li,et al.  Photoacoustic Probes for Ratiometric Imaging of Copper(II). , 2015, Journal of the American Chemical Society.

[34]  Sanjiv S Gambhir,et al.  Family of enhanced photoacoustic imaging agents for high-sensitivity and multiplexing studies in living mice. , 2012, ACS nano.

[35]  Lijun Zhu,et al.  BODIPY-fused porphyrins as soluble and stable near-IR dyes. , 2011, Chemistry.

[36]  W. Dehaen,et al.  Fluorescent indicators based on BODIPY. , 2012, Chemical Society reviews.

[37]  Qian Huang,et al.  Copper sulfide nanoparticles as a new class of photoacoustic contrast agent for deep tissue imaging at 1064 nm. , 2012, ACS nano.

[38]  R. Weissleder,et al.  Fluorescent nanoparticle uptake for brain tumor visualization. , 2006, Neoplasia.

[39]  Liming Nie,et al.  Structural and functional photoacoustic molecular tomography aided by emerging contrast agents. , 2014, Chemical Society reviews.

[40]  R. Weissleder A clearer vision for in vivo imaging , 2001, Nature Biotechnology.

[41]  Changhui Li,et al.  Biocompatible polypyrrole nanoparticles as a novel organic photoacoustic contrast agent for deep tissue imaging. , 2013, Nanoscale.

[42]  Ralph Weissleder,et al.  Protease sensors for bioimaging , 2003, Analytical and bioanalytical chemistry.

[43]  Jesse V. Jokerst,et al.  Construction and Validation of Nano Gold Tripods for Molecular Imaging of Living Subjects , 2014, Journal of the American Chemical Society.

[44]  Tristan Barrett,et al.  Selective molecular imaging of viable cancer cells with pH-activatable fluorescence probes , 2009, Nature Medicine.

[45]  Anthony Harriman,et al.  The chemistry of fluorescent bodipy dyes: versatility unsurpassed. , 2008, Angewandte Chemie.

[46]  Xin Cai,et al.  Noninvasive photoacoustic and fluorescence sentinel lymph node identification using dye-loaded perfluorocarbon nanoparticles. , 2011, ACS nano.

[47]  Lihong V. Wang,et al.  Photoacoustic Tomography: In Vivo Imaging from Organelles to Organs , 2012, Science.