Facile synthesis of chlorin bioconjugates by a series of click reactions

Gonzales, Junior; Bhupathiraju, N. V. S. Dinesh K.; Perea, William; Chu, Huong; Berisha, Naxhije; Bueno, Veronica; Dodic, Naser; Rozenberg, Julia; Greenbaum, Nancy L.; Drain, Charles Michael

doi:10.1039/c7cc01265a

Cited by 13 publications

(31 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…One attraction of the de novo synthesis approach is the ability to achieve wavelength tunability across a family of chlorins, but doing so requires considerable synthetic effort. A less synthetically demanding route to a PEGylated bioconjugatable chlorin (without wavelength tunability) entails derivatization of a porphyrin [ 75 ]. While the design features for a palette of wavelength-tuned chlorins are now known to some extent, and approaches toward a number of desired architectural embodiments also have been established, an unsolved challenge entails how to create diverse chlorins in a concise and facile synthesis amenable to non-specialists.…”

Section: Discussionmentioning

confidence: 99%

Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media

Liu

Hood

et al. 2018

Molecules

View full text Add to dashboard Cite

Fluorophores that absorb and emit in the red spectral region (600–700 nm) are of great interest in photochemistry and photomedicine. Eight new target chlorins (and 19 new chlorins altogether)—analogues of chlorophyll—of different polarities have been designed and synthesized for various applications; seven of the chlorins are equipped with a bioconjugatable tether. Hydrophobic or amphiphilic chlorins in a non-polar organic solvent (toluene), polar organic solvent (DMF), and aqueous or aqueous micellar media show a sharp emission band in the red region and modest fluorescence quantum yield (Φf = 0.2–0.3). A Poisson analysis implies most micelles are empty and few contain >1 chlorin. Water-soluble chlorins each bearing three PEG (oligoethyleneglycol) groups exhibit narrow emission bands (full-width-at-half maximum <25 nm). The lifetime of the lowest singlet excited state and the corresponding yields and rate constants for depopulation pathways (fluorescence, intersystem crossing, internal conversion) are generally little affected by the PEG groups or dissolution in aqueous or organic media. A set of chlorin–avidin conjugates revealed a 2-fold increase in Φf with increased average chlorin/avidin ratio (2.3–12). In summary, the chlorins of various polarities described herein are well suited as red-emitting fluorophores for applications in aqueous or organic media.

show abstract

Section: Discussionmentioning

confidence: 99%

Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media

Liu

Hood

et al. 2018

Molecules

View full text Add to dashboard Cite

show abstract

“…This enhanced phototoxicity in HT-1376 cancer cells was justified by considering the ability of 34 to accumulate in the mitochondria, mediated by glucose transporter 1(GLUT1), in the period between single and repeated irradiation. In 2017, Drain and co-workers 56 selected the NH chlorin 35, obtained from the reaction of 9 with paraformaldehyde and glycine (ylide AZ3), to obtain the chlorin derivative 36 and from this one the multifunctional chlorin platforms 37 and 38 appended with short polyethylene glycols [2-(2methoxyethoxy)ethanol (O-PEG) and 2-(2-methoxyethoxy)ethanethiol (S-PEG) groups] and a carboxylate-linker (Scheme 8). This acid linker was considered to allow a rapid conjugation of the chlorins to bio targeting motifs such as proteins and oligonucleotides.…”

Section: Reaction Of Porphyrins With Azomethine Ylidesmentioning

confidence: 99%

“…Structures of the cationic meso-tetrakis(pentafluorophenyl)chlorin (56) and isobacteriochlorin (57).…”

Section: Figure 15mentioning

confidence: 99%

Synthesis of chlorins and bacteriochlorins from cycloaddition reactions with porphyrins

Cavaleiro¹,

Moura²,

Monteiro³

et al. 2022

Arkivoc

View full text Add to dashboard Cite

show abstract

“…Chlorin-FL (ChL-FL) was prepared following our previous report. 27 Acetonitrile (ACN) and water (H 2 O) were of high-performance liquid chromatography (HPLC) grade and of liquid chromatography mass spectroscopy (LCMS) grade, respectively. Phosphate-buffered saline (PBS) without Ca 2+ or Mg 2+ was obtained from the Media Preparation Facility at Memorial Sloan Kettering Cancer Center and used for all in vivo injections.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Bimodal Imaging of Mouse Peripheral Nerves with Chlorin Tracers

et al. 2021

Self Cite

View full text Add to dashboard Cite

Almost 17 million Americans have a history of cancer, a number expected to reach over 22 million by 2030. Cancer patients often undergo chemotherapy in the form of antineoplastic agents such as cis-platin and paclitaxel. Though effective, these agents can induce debilitating side effects; the most common neurotoxic effect, chemotherapy-induced peripheral neuropathy (CIPN), can endure long after treatment ends. Despite the widespread and chronic nature of the dysfunction, no tools exist to quantitatively measure chemotherapy-induced peripheral neuropathy. Such a tool would not only benefit patients but their stratification could also save significant financial and social costs associated with neuropathic pain. In our first step toward addressing this unmet clinical need, we explored a novel dual approach to localize peripheral nerves: Cerenkov luminescence imaging (CLI) and fluorescence imaging (FI). Our approach revolves around the targeting and imaging of voltage-gated sodium channel subtype Na V 1.7, highly expressed in peripheral nerves from both harvested human and mouse tissues. For the first time, we show that Hsp1a, a radiolabeled Na V 1.7-selective peptide isolated from Homoeomma spec. Peru, can serve as a targeted vector for delivering a radioactive sensor to the peripheral nervous system. In situ, we observe high signal-to-noise ratios in the sciatic nerves of animals injected with fluorescently labeled Hsp1a and radiolabeled Hsp1a. Moreover, confocal microscopy on fresh nerve tissue shows the same high ratios of fluorescence, corroborating our in vivo results. This study indicates that fluorescently labeled and radiolabeled Hsp1a tracers could be used to identify and demarcate nerves in a clinical setting.

show abstract

Facile synthesis of chlorin bioconjugates by a series of click reactions

Cited by 13 publications

References 20 publications

Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media

Chlorophyll-Inspired Red-Region Fluorophores: Building Block Synthesis and Studies in Aqueous Media

Synthesis of chlorins and bacteriochlorins from cycloaddition reactions with porphyrins

Bimodal Imaging of Mouse Peripheral Nerves with Chlorin Tracers

Contact Info

Product

Resources

About