A chemically stable fluorescent marker of the ureter
Open accessAbstract
Surgical methods guided by exogenous fluorescent markers have the potential to define tissue types in real time. Small molecule dyes with efficient and selective renal clearance could enable visualization of the ureter during surgical procedures involving the abdomen and pelvis. These studies report the design and synthesis of a water soluble, net neutral C4'-O-alkyl heptamethine cyanine, Ureter-Label (UL)-766, with excellent properties for ureter visualization. This compound is accessed through a concise synthetic sequence involving an N- to O-transposition reaction that provides other inaccessible C4'-O-alkyl heptamethine cyanines. Unlike molecules containing a C4'-O-aryl substituent, which have also been used for ureter visualization, UL-766 is not reactive towards glutathione and the cellular proteome. In addition, rat models of abdominal surgery reveal that UL-766 undergoes efficient and nearly exclusive renal clearance in vivo. In total, this molecule represents a promising candidate for visualizing the ureter during a variety of surgical interventions.
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The common issue of low chemical stability and reduced fluorescence intensity of polymethines in an aqueous environment can be overcome by proper charge balancing and the introduction of steric shielding.
“The common issue of low chemical stability and reduced fluorescence intensity of polymethines in an aqueous environment can be overcome by proper charge balancing and the introduction of steric shielding.29,32,33”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [32]
The supplied passage labelled Abstract (page not provided) says that a charged group near the cyanine polyene can mitigate undesirable H-aggregation, and reports that the propyl-linker dye resisted thiol reaction in aqueous buffer. It does not establish that steric shielding and charge balancing together overcome reduced fluorescence intensity or broadly solve the chemical-stability problem for polymethines in water. (LLM, conf=0.84)
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References 25 · Cited by 59
- Authors
- Cha, J., Nani, R. R., Luciano, M. P., Kline, G., Broch, A., Kim, K., Namgoong, J.-M., Kulkarni, R. A., Meier, J. L., Kim, P., & Schnermann, M. J.
- Affiliations
- Children's National (US)
- National Cancer Institute (US)
- Frederick National Laboratory for Cancer Research (US)
- Corresponding author
- Cha, Jaepyeong
- Schnermann, Martin J.
- ORCID
- Venue
- Bioorganic & Medicinal Chemistry Letters
- Publisher
- Elsevier BV
- Published
- 2018-09
- Volume
- 28
- Issue
- 16
- Pages
- 2741-2745
- ISSN
- 0960-894X (ISSN-L)
- PMC
- PMC6437767
- OpenAlex
- W2789655593
- Cited by
- 59
- References
- 25
- Citations by year
- 2026: 5 · 2025: 5 · 2024: 5 · 2023: 7 · 2022: 8 · 2021: 10 · 2020: 11 · 2019: 5 · 2018: 3
- FWCI
- 3.13
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Licence
- Locations
- Bioorganic & Medicinal Chemistry Letters (acceptedVersion)
- PubMed (publishedVersion)
- Europe PMC (PubMed Central) (acceptedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Institutes of Health
- National Cancer Institute
- Center for Cancer Research
- Sheikh Zayed Institute for Pediatric Surgical Innovation
- Topics
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Health Sciences › Medicine › Radiology, Nuclear Medicine and Imaging › Optical Imaging and Spectroscopy Techniques
- Keywords
- fluorescent markers, heptamethine cyanine, renal clearance, glutathione resistance, abdominal surgery, dye synthesis
- MeSH terms
- Animals, Dose-Response Relationship, Drug, Fluorescent Dyes, Humans, Injections, Intravenous, Structure-Activity Relationship, Tissue Distribution, Ureter, Molecular Structure, Biomarkers, Rats, HEK293 Cells
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