Fluorescein-thiourea-PEG2-azide

 CAS No.: 1146195-72-3  Cat No.: BP-500631  Purity: 96% 4.5  

Fluorescein-thiourea-PEG2-azide is a bifunctional PROTAC linker construct combining a fluorescein fluorophore with a thiourea-derived handle and a short polyethylene glycol spacer terminating in an azide group. Structurally, it features a PEG2 chain that provides aqueous solubility and spatial separation between the recognition/conjugation sites, while the thiourea linkage offers a stable connection motif commonly used to tune linker electronics and reactivity for subsequent coupling. In targeted protein degradation workflows, the azide enables bioorthogonal conjugation (typically via copper-free azide–alkyne cycloaddition) to attach the linker to a complementary alkyne-bearing ligand or warhead-bearing component, allowing assembly of fluorescently traceable PROTACs. The fluorescein tag facilitates experimental monitoring of conjugation efficiency, cellular uptake, and intracellular localization, supporting optimization of linker length and attachment geometry. This reagent is therefore valuable for mechanistic studies and iterative PROTAC design where visualization and controlled modular assembly are required.

Fluorescein-thiourea-PEG2-azide

Structure of 1146195-72-3

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Category
PROTAC Linker
Molecular Formula
C₂₇H₂₅N₅O₇S
Molecular Weight
563.58

* For research and manufacturing use only. Not for human or clinical use.

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Purity
96%
Solubility
DMSO, DMF, DCM
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
1-[2-[2-(2-azidoethoxy)ethoxy]ethyl]-3-(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)thiourea
Synonyms
Fluorescein-PEG2-azide
Excitation
494
Emission
517
InChI Key
ZLPFCAHUXVVHPW-UHFFFAOYSA-N
InChI
InChI=1S/C27H25N5O7S/c28-32-30-8-10-37-12-11-36-9-7-29-26(40)31-16-1-4-20-19(13-16)25(35)39-27(20)21-5-2-17(33)14-23(21)38-24-15-18(34)3-6-22(24)27/h1-6,13-15,33-34H,7-12H2,(H2,29,31,40)
SMILES
C1=CC2=C(C=C1NC(=S)NCCOCCOCCN=[N+]=[N-])C(=O)OC23C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O

Fluorescein-thiourea-PEG2-azide, combines a thiourea-derived fluorescein motif with a short polyethylene glycol spacer terminating in an azide handle. The linker is designed to support efficient conjugation chemistry in targeted protein degradation workflows, enabling attachment to ligands while providing a built-in fluorescent tag for monitoring synthesis and assembly. The points below describe its structure and practical reactivity for PROTAC construction in detail.

Structure: The molecule features a fluorescein-thiourea core connected to a short PEG chain and capped with a terminal azide. It contains aromatic rings, a thiourea linkage, and ether functionalities from the PEG segment. The azide provides a stable, bioorthogonal reactive group, while the fluorescein unit offers strong fluorescence for tracking.

Reactivity: The azide functionality is well suited for copper-catalyzed azide–alkyne cycloaddition or related bioorthogonal coupling strategies to connect the linker to alkyne-bearing PROTAC ligands. Typical preparations use inert atmosphere, appropriate copper sources and ligands, and polar organic or mixed solvent systems compatible with fluorescein stability. Reaction progress can often be monitored by fluorescence, and the thiourea and fluorescein groups generally tolerate mild coupling conditions used for click-type conjugations.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
g/mol
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