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Sigma-Aldrich

NVOC2-Q-rhodamine-5-PEG3-azide

95%

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Synonym(s):
ortho-Nitroveratryloxycarbonyl-Q-rhodamine-5-PEG3-azide
Empirical Formula (Hill Notation):
C55H56N8O19
CAS Number:
1352809-21-2
Molecular Weight:
1133.08
MDL number:
MFCD24849720
UNSPSC Code:
12352200
PubChem Substance ID:
329767394
NACRES:
NA.22

Assay

95%

form

solid

reaction suitability

reaction type: click chemistry

mp

178-282 °C (decomposition)

storage temp.

−20°C

SMILES string

COc1cc(COC(=O)N2CCCc3cc4c(Oc5cc6N(CCCc6cc5C47OC(=O)c8cc(ccc78)C(=O)NCCOCCOCCOCCN=[N+]=[N-])C(=O)OCc9cc(OC)c(OC)cc9[N+]([O-])=O)cc23)c(cc1OC)[N+]([O-])=O

InChI

1S/C55H56N8O19/c1-72-47-24-35(43(62(68)69)28-49(47)74-3)30-79-53(66)60-13-5-7-32-22-39-45(26-41(32)60)81-46-27-42-33(8-6-14-61(42)54(67)80-31-36-25-48(73-2)50(75-4)29-44(36)63(70)71)23-40(46)55(39)38-10-9-34(21-37(38)52(65)82-55)51(64)57-11-15-76-17-19-78-20-18-77-16-12-58-59-56/h9-10,21-29H,5-8,11-20,30-31H2,1-4H3,(H,57,64)

InChI key

IWBUKVVLULQKCE-UHFFFAOYSA-N

Application

Photoactivatable rhodamine derivative functionalized with a PEG azide. The azide functionality can be used to conjugate this caged rhodamine to alkyne or cycloalkyne containing compounds or biomolecules using the azide-alkyne cycloaddition click chemistry reaction. The ortho-Nitroveratryloxycarbonyl (NVOC) cages can be removed upon irradiation with UV light, restoring the fluorescence of the base dye. NVOC has an absorption max at ~350 nm and has been shown to be cleaved at 350 nm, 405 nm and 420 nm.

Q-Rhodamine λ(ex) = 537 nm, λ(em) = 556 nm.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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K R Gee et al.
Bioorganic & medicinal chemistry letters, 11(16), 2181-2183 (2001-08-22)
An amine-reactive caged rhodamine was synthesized and conjugated to aminodextran. The resulting tracer was injected into a single cell zebrafish embryo, and a portion of the tracer was photolyzed in a single cell after development. The resulting fluorescent cell was
Facile and general synthesis of photoactivatable xanthene dyes.
Laura M Wysocki et al.
Angewandte Chemie (International ed. in English), 50(47), 11206-11209 (2011-09-29)

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