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Chemical Structure| 1145-80-8 Chemical Structure| 1145-80-8
Chemical Structure| 1145-80-8

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Cbz-Ser-OH is a serine derivative widely used in peptide synthesis. Serine plays a key role in cell signaling and metabolic pathways, and this compound is applied in signal transduction protein and enzyme mechanism research.

Synonyms: Z-Ser-OH

4.5 *For Research Use Only !

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Product Citations

Product Citations

Wang, Cuihua ; Motlagh, Negin Jalali ; Wojtkiewicz, Gregory R ; Yang, Hongzhi ; Kim, Hyung-Hwan ; Chen, John W

Abstract: Rationale: The mannose receptor (CD206, expressed by the gene Mrc1) is a surface marker overexpressed by anti-inflammatory and pro-tumoral macrophages. As such, CD206+ macrophages play key roles in the immune response to different pathophysiological conditions and represent a promising diagnostic and therapeutic target. However, methods to specifically target these cells remain challenging. In this study, we describe a multi-mannose approach to develop CD206-targeting fluorescent and MRI agents that specifically and sensitively detect and monitor CD206+ macrophage immune response in different disease conditions. Methods: We designed and synthesized fluorescent agents MR1-cy5 and MR2-cy5, and MRI agents Mann2-DTPA-Gd and MannGdFish. Cellular assays using pro-inflammatory and anti-inflammatory macrophages differentiated from RAW 264.7 cells were performed, and signals were detected by fluorescence microscopy and inductively coupled plasma mass spectrometry (ICP-MS) to validate specificity in vitro. In vivo specificity and efficacy of the agents were evaluated by MRI in a subcutaneous wound healing model and experimental glioma with Mrc1+/+ without and with D-mannose treatment, Mrc1+/-, and Mrc1-/- mice, and in stroke. One-way ANOVA and two-way ANOVA tests were used for data analysis. P < 0.05 was considered statistically different. Results: Both in vitro fluorescence imaging with MR2-cy5, ICP-MS with Mann2-DTPA-Gd, and in vivo MRI in Mrc1-/- mice confirmed the specificity of our approach. Mann2-DTPA-Gd MRI can track the changes of CD206+ macrophages at different stages of wound healing, correlating well with flow cytometry data using another anti-inflammatory macrophage marker (arginase-1). The specificity and efficacy of Mann2-DPTA-Gd were further validated in experimental glioma, in which Mann2-DTPA-Gd imaging detected CD206+ tumor-associated macrophages (TAMs), demonstrated significantly decreased signals in Mrc1+/- mice and Mrc1-/- mice, and tracked treatment changes in D-mannose-treated Mrc1+/+ mice. Furthermore, Mann2-DTPA-Gd can report microglia/macrophages and correlate with histology in stroke. The more Gd-stable agent MannGdFish demonstrated similar efficacy as Mann2-DTPA-Gd in vivo with favorable biodistribution and pharmacokinetics. Conclusion: We have developed a fluorescent agent (MR2-cy5) and MRI agents (Mann2-DTPA-Gd and MannGdFish) with two mannose moieties that are highly specific to CD206 and can track CD206+ macrophages in disease models of wound healing, tumor, and neurological disease. Importantly, MannGdFish, with its high specificity, stability, favorable biodistribution, and pharmacokinetics, is a promising translational candidate to noninvasively monitor CD206+ macrophages in repair/regeneration and tumors in patients. In addition, with the specific binding motif to CD206, other imaging modalities and therapeutic agents could also be introduced for theranostic applications.

Keywords: molecular magnetic resonance imaging ; mannose receptor (CD206) ; tumor-associated macrophages ; wound healing ; glioma ; stroke

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Product Details of Cbz-Ser-OH

CAS No. :1145-80-8
Formula : C11H13NO5
M.W : 239.22
SMILES Code : OC[C@@H](C(O)=O)NC(OCC1=CC=CC=C1)=O
Synonyms :
Z-Ser-OH
MDL No. :MFCD00002662
InChI Key :GNIDSOFZAKMQAO-VIFPVBQESA-N
Pubchem ID :100310

Safety of Cbz-Ser-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Cbz-Ser-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1145-80-8 ]

[ 1145-80-8 ] Synthesis Path-Downstream   1~8

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  • [ 114519-10-7 ]
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  • [ 104926-48-9 ]
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  • [ 4089-07-0 ]
  • (S)-2-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid ethyl ester [ No CAS ]
  • 7
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  • [ 19647-68-8 ]
  • 8
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  • methylammonium hydrochloride [ No CAS ]
  • [ 19647-68-8 ]
 

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