PMID- 30809281
OWN - NLM
STAT- MEDLINE
DCOM- 20191209
LR  - 20200309
IS  - 1838-7640 (Electronic)
IS  - 1838-7640 (Linking)
VI  - 9
IP  - 2
DP  - 2019
TI  - Highly-Soluble Cyanine J-aggregates Entrapped by Liposomes for In Vivo Optical 
      Imaging around 930 nm.
PG  - 381-390
LID - 10.7150/thno.28376 [doi]
AB  - Near infrared (NIR) dyes are useful for in vivo optical imaging. Liposomes have 
      been used extensively for delivery of diverse cargos, including hydrophilic 
      cargos which are passively loaded in the aqueous core. However, most currently 
      available NIR dyes are only slightly soluble in water, making passive entrapment 
      in liposomes challenging for achieving high optical contrast. Methods: We 
      modified a commercially-available NIR dye (IR-820) via one-step Suzuki coupling 
      with dicarboxyphenylboronic acid, generating a disulfonated heptamethine; 
      dicarboxyphenyl cyanine (DCP-Cy). DCP-Cy was loaded in liposomes and used for 
      optical imaging. Results: Owing to increased charge in mildly basic aqueous 
      solution, DCP-Cy had substantially higher water solubility than indocyanine green 
      (by an order of magnitude), resulting in higher NIR absorption. Unexpectedly, 
      DCP-Cy tended to form J-aggregates with pronounced spectral red-shifting to 934 
      nm (from 789 nm in monomeric form). J-aggregate formation was dependent on salt 
      and DCP-Cy concentration. Dissolved at 20 mg/mL, DCP-Cy J-aggregates could be 
      entrapped in liposomes. Full width at half maximum absorption of the 
      liposome-entrapped dye was just 25 nm. The entrapped DCP-Cy was readily 
      detectable by fluorescence and photoacoustic NIR imaging. Upon intravenous 
      administration to mice, liposomal DCP-Cy circulated substantially longer than the 
      free dye. Accumulation was largely in the spleen, which was visualized with 
      fluorescence and photoacoustic imaging. Conclusions: DCP-Cy is simple to 
      synthesize and exhibits high aqueous solubility and red-shifted absorption from 
      J-aggregate formation. Liposomal dye entrapment is possible, which facilitates in 
      vivo photoacoustic and fluorescence imaging around 930 nm.
FAU - Miranda, Dyego
AU  - Miranda D
AD  - Department of Biomedical Engineering, University at Buffalo, State University of 
      New York, Buffalo, NY 14260, USA.
FAU - Huang, Haoyuan
AU  - Huang H
AD  - Department of Biomedical Engineering, University at Buffalo, State University of 
      New York, Buffalo, NY 14260, USA.
FAU - Kang, Homan
AU  - Kang H
AD  - Gordon Center for Medical Imaging, Department of Radiology, Massachusetts General 
      Hospital and Harvard Medical School, Boston, MA 02114, USA.
FAU - Zhan, Ye
AU  - Zhan Y
AD  - Department of Biomedical Engineering, University at Buffalo, State University of 
      New York, Buffalo, NY 14260, USA.
FAU - Wang, Depeng
AU  - Wang D
AD  - Department of Biomedical Engineering, University at Buffalo, State University of 
      New York, Buffalo, NY 14260, USA.
FAU - Zhou, Yang
AU  - Zhou Y
AD  - College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal 
      University, Jinan 250014, China.
FAU - Geng, Jumin
AU  - Geng J
AD  - Department of Biomedical Engineering, University at Buffalo, State University of 
      New York, Buffalo, NY 14260, USA.
FAU - Kilian, Hailey I
AU  - Kilian HI
AD  - Department of Biomedical Engineering, University at Buffalo, State University of 
      New York, Buffalo, NY 14260, USA.
FAU - Stiles, Wesley
AU  - Stiles W
AD  - Gordon Center for Medical Imaging, Department of Radiology, Massachusetts General 
      Hospital and Harvard Medical School, Boston, MA 02114, USA.
FAU - Razi, Aida
AU  - Razi A
AD  - Department of Anatomy and Cell Biology, McGill University, Montreal, Quebec, H3A 
      0C7, Canada.
FAU - Ortega, Joaquin
AU  - Ortega J
AD  - Department of Anatomy and Cell Biology, McGill University, Montreal, Quebec, H3A 
      0C7, Canada.
FAU - Xia, Jun
AU  - Xia J
AD  - Department of Biomedical Engineering, University at Buffalo, State University of 
      New York, Buffalo, NY 14260, USA.
FAU - Choi, Hak Soo
AU  - Choi HS
AD  - Gordon Center for Medical Imaging, Department of Radiology, Massachusetts General 
      Hospital and Harvard Medical School, Boston, MA 02114, USA.
FAU - Lovell, Jonathan F
AU  - Lovell JF
AD  - Department of Biomedical Engineering, University at Buffalo, State University of 
      New York, Buffalo, NY 14260, USA.
LA  - eng
GR  - DP5 OD017898/OD/NIH HHS/United States
GR  - R01 EB017270/EB/NIBIB NIH HHS/United States
PT  - Journal Article
PT  - Research Support, N.I.H., Extramural
PT  - Research Support, Non-U.S. Gov't
PT  - Research Support, U.S. Gov't, Non-P.H.S.
DEP - 20190101
PL  - Australia
TA  - Theranostics
JT  - Theranostics
JID - 101552395
RN  - 0 (Coloring Agents)
RN  - 0 (Fluorescent Dyes)
RN  - 0 (Liposomes)
RN  - IX6J1063HV (Indocyanine Green)
SB  - IM
MH  - Administration, Intravenous
MH  - Animals
MH  - Coloring Agents/*administration & dosage/chemical synthesis/chemistry
MH  - Fluorescent Dyes/*administration & dosage/chemical synthesis/chemistry
MH  - Indocyanine Green/*administration & dosage/chemical synthesis/chemistry
MH  - Liposomes/*administration & dosage
MH  - Mice
MH  - Optical Imaging/*methods
MH  - Photoacoustic Techniques/*methods
MH  - Solubility
PMC - PMC6376187
OTO - NOTNLM
OT  - J-aggregate
OT  - cyanine
OT  - liposomes
OT  - photoacoustic
COIS- Competing Interests: The authors have declared that no competing interest exists.
EDAT- 2019/02/28 06:00
MHDA- 2019/12/18 06:00
PMCR- 2019/01/01
CRDT- 2019/02/28 06:00
PHST- 2018/07/08 00:00 [received]
PHST- 2018/11/16 00:00 [accepted]
PHST- 2019/02/28 06:00 [entrez]
PHST- 2019/02/28 06:00 [pubmed]
PHST- 2019/12/18 06:00 [medline]
PHST- 2019/01/01 00:00 [pmc-release]
AID - thnov09p0381 [pii]
AID - 10.7150/thno.28376 [doi]
PST - epublish
SO  - Theranostics. 2019 Jan 1;9(2):381-390. doi: 10.7150/thno.28376. eCollection 2019.