Tuning the photophysical properties of cyanine by barbiturate functionalization and nanoformulation for efficient optoacoustics- guided phototherapy

Research output: Contribution to journalArticleResearchpeer review

Authors

  • Nian Liu
  • Patrick O'Connor
  • Vipul Gujrati
  • Divyesh Shelar
  • Xiaopeng Ma
  • Pia Anzenhofer
  • Uwe Klemm
  • Xinhui Su
  • Yuanhui Huang
  • Karin Kleigrewe
  • Annette Feuchtinger
  • Axel Walch
  • Michael Sattler
  • Oliver Plettenburg
  • Vasilis Ntziachristos

External Research Organisations

  • Zhejiang University
  • Technical University of Munich (TUM)
  • Helmholtz Zentrum München - German Research Center for Environmental Health
  • Shandong University
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Details

Original languageEnglish
Pages (from-to)522-530
Number of pages9
JournalJournal of controlled release
Volume372
Early online date27 Jun 2024
Publication statusPublished - Aug 2024

Abstract

Cyanine derivatives are organic dyes widely used for optical imaging. However, their potential in longitudinal optoacoustic imaging and photothermal therapy remains limited due to challenges such as poor chemical stability, poor photostability, and low photothermal conversion. In this study, we present a new structural modification for cyanine dyes by introducing a strongly electron-withdrawing group (barbiturate), resulting in a new series of barbiturate-cyanine dyes (BC810, BC885, and BC1010) with suppressed fluorescence and enhanced stability. Furthermore, the introduction of BC1010 into block copolymers (PEG114-b-PCL60) induces aggregation-caused quenching, further boosting the photothermal performance. The photophysical properties of nanoparticles (BC1010-NPs) include their remarkably broad absorption range from 900 to 1200 nm for optoacoustic imaging, allowing imaging applications in NIR-I and NIR-II windows. The combined effect of these strategies, including improved photostability, enhanced nonradiative relaxation, and aggregation-caused quenching, enables the detection of optoacoustic signals with high sensitivity and effective photothermal treatment of in vivo tumor models when BC1010-NPs are administered before irradiation with a 1064 nm laser. This research introduces a barbiturate-functionalized cyanine derivative with optimal properties for efficient optoacoustics-guided theranostic applications. This new compound holds significant potential for biomedical use, facilitating advancements in optoacoustic-guided diagnostic and therapeutic approaches.

Keywords

    Barbiturate functionalization, Cyanine, Nanoformulation, NIR-II excitation, Optoacoustic, Photothermal therapy

ASJC Scopus subject areas

Cite this

Tuning the photophysical properties of cyanine by barbiturate functionalization and nanoformulation for efficient optoacoustics- guided phototherapy. / Liu, Nian; O'Connor, Patrick; Gujrati, Vipul et al.
In: Journal of controlled release, Vol. 372, 08.2024, p. 522-530.

Research output: Contribution to journalArticleResearchpeer review

Liu, N, O'Connor, P, Gujrati, V, Shelar, D, Ma, X, Anzenhofer, P, Klemm, U, Su, X, Huang, Y, Kleigrewe, K, Feuchtinger, A, Walch, A, Sattler, M, Plettenburg, O & Ntziachristos, V 2024, 'Tuning the photophysical properties of cyanine by barbiturate functionalization and nanoformulation for efficient optoacoustics- guided phototherapy', Journal of controlled release, vol. 372, pp. 522-530. https://doi.org/10.1016/j.jconrel.2024.06.037
Liu, N., O'Connor, P., Gujrati, V., Shelar, D., Ma, X., Anzenhofer, P., Klemm, U., Su, X., Huang, Y., Kleigrewe, K., Feuchtinger, A., Walch, A., Sattler, M., Plettenburg, O., & Ntziachristos, V. (2024). Tuning the photophysical properties of cyanine by barbiturate functionalization and nanoformulation for efficient optoacoustics- guided phototherapy. Journal of controlled release, 372, 522-530. https://doi.org/10.1016/j.jconrel.2024.06.037
Liu N, O'Connor P, Gujrati V, Shelar D, Ma X, Anzenhofer P et al. Tuning the photophysical properties of cyanine by barbiturate functionalization and nanoformulation for efficient optoacoustics- guided phototherapy. Journal of controlled release. 2024 Aug;372:522-530. Epub 2024 Jun 27. doi: 10.1016/j.jconrel.2024.06.037
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title = "Tuning the photophysical properties of cyanine by barbiturate functionalization and nanoformulation for efficient optoacoustics- guided phototherapy",
abstract = "Cyanine derivatives are organic dyes widely used for optical imaging. However, their potential in longitudinal optoacoustic imaging and photothermal therapy remains limited due to challenges such as poor chemical stability, poor photostability, and low photothermal conversion. In this study, we present a new structural modification for cyanine dyes by introducing a strongly electron-withdrawing group (barbiturate), resulting in a new series of barbiturate-cyanine dyes (BC810, BC885, and BC1010) with suppressed fluorescence and enhanced stability. Furthermore, the introduction of BC1010 into block copolymers (PEG114-b-PCL60) induces aggregation-caused quenching, further boosting the photothermal performance. The photophysical properties of nanoparticles (BC1010-NPs) include their remarkably broad absorption range from 900 to 1200 nm for optoacoustic imaging, allowing imaging applications in NIR-I and NIR-II windows. The combined effect of these strategies, including improved photostability, enhanced nonradiative relaxation, and aggregation-caused quenching, enables the detection of optoacoustic signals with high sensitivity and effective photothermal treatment of in vivo tumor models when BC1010-NPs are administered before irradiation with a 1064 nm laser. This research introduces a barbiturate-functionalized cyanine derivative with optimal properties for efficient optoacoustics-guided theranostic applications. This new compound holds significant potential for biomedical use, facilitating advancements in optoacoustic-guided diagnostic and therapeutic approaches.",
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T1 - Tuning the photophysical properties of cyanine by barbiturate functionalization and nanoformulation for efficient optoacoustics- guided phototherapy

AU - Liu, Nian

AU - O'Connor, Patrick

AU - Gujrati, Vipul

AU - Shelar, Divyesh

AU - Ma, Xiaopeng

AU - Anzenhofer, Pia

AU - Klemm, Uwe

AU - Su, Xinhui

AU - Huang, Yuanhui

AU - Kleigrewe, Karin

AU - Feuchtinger, Annette

AU - Walch, Axel

AU - Sattler, Michael

AU - Plettenburg, Oliver

AU - Ntziachristos, Vasilis

N1 - Publisher Copyright: © 2023

PY - 2024/8

Y1 - 2024/8

N2 - Cyanine derivatives are organic dyes widely used for optical imaging. However, their potential in longitudinal optoacoustic imaging and photothermal therapy remains limited due to challenges such as poor chemical stability, poor photostability, and low photothermal conversion. In this study, we present a new structural modification for cyanine dyes by introducing a strongly electron-withdrawing group (barbiturate), resulting in a new series of barbiturate-cyanine dyes (BC810, BC885, and BC1010) with suppressed fluorescence and enhanced stability. Furthermore, the introduction of BC1010 into block copolymers (PEG114-b-PCL60) induces aggregation-caused quenching, further boosting the photothermal performance. The photophysical properties of nanoparticles (BC1010-NPs) include their remarkably broad absorption range from 900 to 1200 nm for optoacoustic imaging, allowing imaging applications in NIR-I and NIR-II windows. The combined effect of these strategies, including improved photostability, enhanced nonradiative relaxation, and aggregation-caused quenching, enables the detection of optoacoustic signals with high sensitivity and effective photothermal treatment of in vivo tumor models when BC1010-NPs are administered before irradiation with a 1064 nm laser. This research introduces a barbiturate-functionalized cyanine derivative with optimal properties for efficient optoacoustics-guided theranostic applications. This new compound holds significant potential for biomedical use, facilitating advancements in optoacoustic-guided diagnostic and therapeutic approaches.

AB - Cyanine derivatives are organic dyes widely used for optical imaging. However, their potential in longitudinal optoacoustic imaging and photothermal therapy remains limited due to challenges such as poor chemical stability, poor photostability, and low photothermal conversion. In this study, we present a new structural modification for cyanine dyes by introducing a strongly electron-withdrawing group (barbiturate), resulting in a new series of barbiturate-cyanine dyes (BC810, BC885, and BC1010) with suppressed fluorescence and enhanced stability. Furthermore, the introduction of BC1010 into block copolymers (PEG114-b-PCL60) induces aggregation-caused quenching, further boosting the photothermal performance. The photophysical properties of nanoparticles (BC1010-NPs) include their remarkably broad absorption range from 900 to 1200 nm for optoacoustic imaging, allowing imaging applications in NIR-I and NIR-II windows. The combined effect of these strategies, including improved photostability, enhanced nonradiative relaxation, and aggregation-caused quenching, enables the detection of optoacoustic signals with high sensitivity and effective photothermal treatment of in vivo tumor models when BC1010-NPs are administered before irradiation with a 1064 nm laser. This research introduces a barbiturate-functionalized cyanine derivative with optimal properties for efficient optoacoustics-guided theranostic applications. This new compound holds significant potential for biomedical use, facilitating advancements in optoacoustic-guided diagnostic and therapeutic approaches.

KW - Barbiturate functionalization

KW - Cyanine

KW - Nanoformulation

KW - NIR-II excitation

KW - Optoacoustic

KW - Photothermal therapy

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U2 - 10.1016/j.jconrel.2024.06.037

DO - 10.1016/j.jconrel.2024.06.037

M3 - Article

C2 - 38897293

AN - SCOPUS:85196820955

VL - 372

SP - 522

EP - 530

JO - Journal of controlled release

JF - Journal of controlled release

SN - 0168-3659

ER -

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