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771848

Sigma-Aldrich

NVOC2-5-carboxy-Q-rhodamine-NHS ester

95% (HPLC)

Synonym(s):

1′,11′-bis{[(4,5-dimethoxy-2-nitrobenzyl)oxy]carbonyl}-3-oxo-1′,2′,3′,4′,8′,9′,10′,11′-octahydro-spiro[isobenzofuran-1(3H),6′-pyrano[3,2-g:5,6-g′]diquinoline]-5-carboxylic acid, 5-succinimidyl ester, ortho-nitroveratryloxycarbonyl-Q-rhodamine-5-succinimidyl ester

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About This Item

Empirical Formula (Hill Notation):
C51H43N5O19
CAS Number:
1352809-17-6
Molecular Weight:
1029.91
MDL number:
MFCD26405981
UNSPSC Code:
12352200
PubChem Substance ID:
329767520

Quality Level

100

Assay

95% (HPLC)

form

solid

mp

250-255 °C (decomposition)

storage temp.

−20°C

SMILES string

O=C(C1=C2C=CC(C(ON(C(CC3)=O)C3=O)=O)=C1)OC42C5=C(C=C(N(C(OCC6=CC(OC)=C(OC)C=C6[N+]([O-])=O)=O)CCC7)C7=C5)OC8=C4C=C(CCCN9C(OCC%10=C([N+]([O-])=O)C=C(OC)C(OC)=C%10)=O)C9=C8

InChI

1S/C51H43N5O19/c1-67-41-18-29(37(55(63)64)22-43(41)69-3)24-71-49(61)52-13-5-7-26-16-33-39(20-35(26)52)73-40-21-36-27(8-6-14-53(36)50(62)72-25-30-19-42(68-2)44(70-4)23-38(30)56(65)66)17-34(40)51(33)32-10-9-28(15-31(32)48(60)74-51)47(59)75-54-45(57)11-12-46(54)58/h9-10,15-23H,5-8,11-14,24-25H2,1-4H3

InChI key

ANVQNDABUUZZMB-UHFFFAOYSA-N

Application

Photoactivatable rhodamine derivative functionalized with a succinimidyl ester (NHS). The NHS functionality can be used to conjugate this caged rhodamine to amine containing compounds or biomolecules. 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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBP0560V

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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)
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

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