Shielding Unit Engineering of NIR-II Molecular Fluorophores for Improved Fluorescence Performance and Renal Excretion Ability

Molecular fluorophores emitting in the second near-infrared (NIR-II) window with good renal excretion ability are favorable for in vivo bio-imaging and clinical applications. So far, renally excretable fluorophores are still less studied. Understanding the influences of molecular structure on optical properties and renal excretion abilities are vital for fluorophore optimization. Herein, a series of shielding unit-donor-acceptor-donor-shielding unit (S-D-A-D-S) NIR-II molecular fluorophores are designed and synthesized with dialkoxy chains substituted benzene as the S unit. The anchoring positions of dialkoxy chains on benzene are tuned as meso-2,6, para-2,5, or ortho-3,4 to afford three fluorophores: BGM6P, BGP6P and BGO6P, respectively. Experimental and calculation results reveal that alkoxy side chains anchored closer to the conjugated backbone can provide better protection from water molecules and PEG chains, affording higher fluorescence quantum yield (QY) in aqueous solutions. Further, these side chains can enable good encapsulation of backbone, resulting in decreased binding with albumin and improved renal excretion. Thus, fluorophore BGM6P with meso-2,6-dialkoxy chains exhibits the highest quantum yield and fastest renal excretion. This work emphasizes the important roles of side chain patterns on optimizing NIR-II fluorophores with high brightness and renal excretion ability.

Download Full-text

Uniform Spheres of α-NaYF4:RE3+ (RE=Eu, Tb, Ce, Er, and Tm): Template-Free Synthesis, Multi-Color Photoluminescence, and Their Application in Cellular Imaging

Crystals ◽

10.3390/cryst10020119 ◽

2020 ◽

Vol 10 (2) ◽

pp. 119

Author(s):

Xiaofeng Fan ◽

Laiqin Gu ◽

Yiling Hu ◽

Qi Zhu

Keyword(s):

Near Infrared ◽

Infrared Emission ◽

Particle Sizes ◽

Hydrothermal Processing ◽

High Brightness ◽

Luminescent Probes ◽

Bio Imaging ◽

Template Free ◽

Near Infrared Emission

Uniformly dispersed luminescent probes with a high brightness and high resolution are desired in bio imaging fields. Here, ~100 nm sized and well-dispersed spheres of RE3+ doped α-NaYF4 (rare earth (RE) = Eu, Tb, Ce, Er, and Tm) have been facile synthesized through hydrothermal processing in the absence of a template, followed by a proper annealing. The processing window of the cubic structured spheres is wide, because the hydrothermal products are independent of the processing conditions, including reaction time and temperature. The original morphology and crystal structure can be well retained with a calcination temperature up to 600 °C. However, calcination gives rise to a reduction of particle sizes, as a result of the crystallite growth and densification. Under ultraviolet radiation, α-NaYF4:RE3+ spheres show characteristic f-f emissions of RE3+ (RE = Eu, Tb, Ce, Er, and Tm), and exhibit orange red, green, ultraviolet (UV), blue green, and blue emissions, respectively. Mainly because of the near-infrared emission at ~697 nm (5D0→7F4 transitions of Eu3+), the successful imaging of macrophages was achieved by NH2-NaYF4:Eu3+ probes, indicating their excellent imaging capacity for cells in vitro.

Download Full-text

Subtle changes in network composition impact the biodistribution and tumor accumulation of nanogels

Chemical Communications ◽

10.1039/c8cc05627g ◽

2018 ◽

Vol 54 (83) ◽

pp. 11777-11780 ◽

Cited By ~ 7

Author(s):

Ilona Zilkowski ◽

Ioanna Theodorou ◽

Krystyna Albrecht ◽

Frederic Ducongé ◽

Jürgen Groll

Keyword(s):

Breast Tumor ◽

Tumor Targeting ◽

Near Infrared ◽

Side Chain ◽

Human Breast ◽

Human Breast Tumor ◽

Tumor Xenografts ◽

Network Composition ◽

Tumor Accumulation

We studied the effect of subtle changes in side-chain chemistry and labelling with near infrared fluorophores of nanogels (NGs) prepared from thiolated poly(glycidol) on in vivo biodistribution in mice bearing human breast tumor xenografts. Side chain chemistry as well as labelling clearly influenced tumor targeting and overall biodistribution.

Download Full-text

FadD19 of Rhodococcus rhodochrous DSM43269, a Steroid-Coenzyme A Ligase Essential for Degradation of C-24 Branched Sterol Side Chains

Applied and Environmental Microbiology ◽

10.1128/aem.00380-11 ◽

2011 ◽

Vol 77 (13) ◽

pp. 4455-4464 ◽

Cited By ~ 48

Author(s):

M. H. Wilbrink ◽

M. Petrusma ◽

L. Dijkhuizen ◽

R. van der Geize

Keyword(s):

Mutant Strain ◽

Coenzyme A ◽

Side Chain ◽

Side Chains ◽

Rhodococcus Rhodochrous ◽

Content Type ◽

Coa Ligase ◽

Coenzyme A Ligase ◽

Sequential Inactivation

ABSTRACTThe actinobacterial cholesterol catabolic gene cluster contains a subset of genes that encode β-oxidation enzymes with a putative role in sterol side chain degradation. We investigated the physiological roles of several genes, i.e.,fadD17,fadD19,fadE26,fadE27, andro04690DSM43269, by gene inactivation studies in mutant strain RG32 ofRhodococcus rhodochrousDSM43269. Mutant strain RG32 is devoid of 3-ketosteroid 9α-hydroxylase (KSH) activity and was constructed following the identification, cloning, and sequential inactivation of fivekshAgene homologs in strain DSM43269. We show that mutant strain RG32 is fully blocked in steroid ring degradation but capable of selective sterol side chain degradation. Except for RG32ΔfadD19, none of the mutants constructed in RG32 revealed an aberrant phenotype on sterol side chain degradation compared to parent strain RG32. Deletion offadD19in strain RG32 completely blocked side chain degradation of C-24 branched sterols but interestingly not that of cholesterol. The additional inactivation offadD17in mutant RG32ΔfadD19also did not affect cholesterol side chain degradation. Heterologously expressed FadD19DSM43269nevertheless was active toward steroid-C26-oic acid substrates. Our data identified FadD19 as a steroid-coenzyme A (CoA) ligase with an essentialin vivorole in the degradation of the side chains of C-24 branched-chain sterols. This paper reports the identification and characterization of a CoA ligase with anin vivorole in sterol side chain degradation. The high similarity (67%) between the FadD19DSM43269and FadD19H37Rvenzymes further suggests that FadD19H37Rvhas anin vivorole in sterol metabolism ofMycobacterium tuberculosisH37Rv.

Download Full-text

High-Quantum-Yield Mitochondria-Targeting Near-Infrared Fluorescent Probe for Imaging Native Hypobromous Acid in Living Cells and in Vivo

Analytical Chemistry ◽

10.1021/acs.analchem.6b04094 ◽

2017 ◽

Vol 89 (3) ◽

pp. 1787-1792 ◽

Cited By ~ 32

Author(s):

Xiaojun Liu ◽

Aishan Zheng ◽

Dongrui Luan ◽

Xiaoting Wang ◽

Fanpeng Kong ◽

...

Keyword(s):

Quantum Yield ◽

Fluorescent Probe ◽

Near Infrared ◽

Living Cells ◽

High Quantum Yield ◽

High Quantum ◽

Hypobromous Acid ◽

Mitochondria Targeting

Download Full-text

“CinNapht” Dyes as New Cinnoline/Naphthalimide Fused Hybrids Fluorophores: Synthesis, Photo-Physical Study and Use for Bio-Imaging

10.26434/chemrxiv.14269004.v1 ◽

2021 ◽

Author(s):

Minh-Duc Hoang ◽

Jean-Baptiste Bodin ◽

Farah Savina ◽

Vincent Steinmetz ◽

Jérôme Bignon ◽

...

Keyword(s):

Quantum Yield ◽

Red Emission ◽

Solvatochromic Effect ◽

Physical Study ◽

Donor Acceptor ◽

Bio Imaging ◽

Naphthalimide Dye

Six-membered diaza ring of Cinnoline have been fused on Naphthalimide dye to give donor–acceptor system called CinNapht. These red shifted fluorophore, that can be synthetised in gram scale, exhibits a large Stoke Shift and quantum yield up to 0.33. It is also caracterized by strong solvatochromic effect for green to red emission as well and can be used for bio-imaging

Download Full-text

Glucose-functionalized near-infrared Ag2Se quantum dots with renal excretion ability for long-term in vivo tumor imaging

Journal of Materials Chemistry B ◽

10.1039/c9tb01112a ◽

2019 ◽

Vol 7 (38) ◽

pp. 5782-5788 ◽

Cited By ~ 5

Author(s):

Xiao-Lei Ge ◽

Biao Huang ◽

Zhi-Ling Zhang ◽

Xiaolan Liu ◽

Man He ◽

...

Keyword(s):

Quantum Dots ◽

Fluorescent Probes ◽

Near Infrared ◽

Renal Excretion ◽

Tumor Imaging

Non-toxic and long-term fluorescent probes for tumor imaging are in urgent need for non-invasively obtaining information about tumor genesis and metastasis in vivo.

Download Full-text

Hyperglutamylation of Tubulin Can either Stabilize or Destabilize Microtubules in the Same Cell

Eukaryotic Cell ◽

10.1128/ec.00176-09 ◽

2009 ◽

Vol 9 (1) ◽

pp. 184-193 ◽

Cited By ~ 49

Author(s):

Dorota Wloga ◽

Drashti Dave ◽

Jennifer Meagley ◽

Krzysztof Rogowski ◽

Maria Jerka-Dziadosz ◽

...

Keyword(s):

Chain Length ◽

Eukaryotic Cells ◽

Side Chain ◽

Side Chains ◽

Primary Sequence ◽

Side Chain Length ◽

Length Regulation ◽

Cytoplasmic Microtubules

ABSTRACT In most eukaryotic cells, tubulin is subjected to posttranslational glutamylation, a conserved modification of unclear function. The glutamyl side chains form as branches of the primary sequence glutamic acids in two biochemically distinct steps: initiation and elongation. The length of the glutamyl side chain is spatially controlled and microtubule type specific. Here, we probe the significance of the glutamyl side chain length regulation in vivo by overexpressing a potent side chain elongase enzyme, Ttll6Ap, in Tetrahymena. Overexpression of Ttll6Ap caused hyperelongation of glutamyl side chains on the tubulin of axonemal, cortical, and cytoplasmic microtubules. Strikingly, in the same cell, hyperelongation of glutamyl side chains stabilized cytoplasmic microtubules and destabilized axonemal microtubules. Our observations suggest that the cellular outcomes of glutamylation are mediated by spatially restricted tubulin interactors of diverse nature.

Download Full-text

A stability study of polymer solar cells using conjugated polymers with different donor or acceptor side chain patterns

Journal of Materials Chemistry A ◽

10.1039/c6ta07244e ◽

2016 ◽

Vol 4 (42) ◽

pp. 16677-16689 ◽

Cited By ~ 4

Author(s):

Ilona M. Heckler ◽

Jurgen Kesters ◽

Maxime Defour ◽

Huguette Penxten ◽

Bruno Van Mele ◽

...

Keyword(s):

Solar Cells ◽

Conjugated Polymers ◽

Polymer Solar Cells ◽

Stability Study ◽

Side Chain ◽

Side Chains ◽

Acceptor Side ◽

Donor Acceptor

The position and nature of side chains in the donor–acceptor copolymer were investigated in terms of stability in polymer solar cells.

Download Full-text

Eukaryotic Wobble Uridine Modifications Promote a Functionally Redundant Decoding System

Molecular and Cellular Biology ◽

10.1128/mcb.01542-07 ◽

2008 ◽

Vol 28 (10) ◽

pp. 3301-3312 ◽

Cited By ~ 161

Author(s):

Marcus J. O. Johansson ◽

Anders Esberg ◽

Bo Huang ◽

Glenn R. Björk ◽

Anders S. Byström

Keyword(s):

Saccharomyces Cerevisiae ◽

Side Chain ◽

Side Chains ◽

Methyl Group ◽

Wobble Position ◽

Naturally Occurring

ABSTRACT The translational decoding properties of tRNAs are modulated by naturally occurring modifications of their nucleosides. Uridines located at the wobble position (nucleoside 34 [U34]) in eukaryotic cytoplasmic tRNAs often harbor a 5-methoxycarbonylmethyl (mcm5) or a 5-carbamoylmethyl (ncm5) side chain and sometimes an additional 2-thio (s2) or 2′-O-methyl group. Although a variety of models explaining the role of these modifications have been put forth, their in vivo functions have not been defined. In this study, we utilized recently characterized modification-deficient Saccharomyces cerevisiae cells to test the wobble rules in vivo. We show that mcm5 and ncm5 side chains promote decoding of G-ending codons and that concurrent mcm5 and s2 groups improve reading of both A- and G-ending codons. Moreover, the observation that the mcm5U34- and some ncm5U34-containing tRNAs efficiently read G-ending codons challenges the notion that eukaryotes do not use U-G wobbling.

Download Full-text