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MilliporeSigma

803545

Sigma-Aldrich

SPB (succinimidyl-[4-(psoralen-8-yloxy)]butyrate)

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About This Item

Fórmula empírica (notación de Hill):
C19H15NO8
Peso molecular:
385.32
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22

form

powder

mol wt

385.32

reaction suitability

reagent type: cross-linking reagent

storage condition

desiccated

solubility

DMSO or DMF: soluble

shipped in

ambient

storage temp.

2-8°C

SMILES string

O=C1CCC(N1OC(CCCOC2=C(OC(C=C3)=O)C3=CC4=C2OC=C4)=O)=O

InChI

1S/C19H15NO8/c21-13-4-5-14(22)20(13)28-16(24)2-1-8-25-19-17-12(7-9-26-17)10-11-3-6-15(23)27-18(11)19/h3,6-7,9-10H,1-2,4-5,8H2

InChI key

ZOMXGWWLJXRQKZ-UHFFFAOYSA-N

General description

SPB is an amine-reactive and photoreactive heterobifunctional crosslinking reagent. The photoreactive psoralen group provides much greater covalent insertion yields than phenyl azide-containing compounds, which makes this reagent a superior alternative to typical photoreactive NHS-ester crosslinkers. The psoralen tricyclic planar ring system intercalates into double-stranded, and to a lesser extent, single-stranded, DNA, RNA, PCR products, cDNA or oligonucleotides. It also can be used with agarose gel-purified oligonucleotides because the presence of agarose does not interfere with the coupling reaction. The nucleic acid labeling site of the psoralen group (the 5,6 double bond in thymine residues) does not interfere with subsequent hybridization reactions, creating a highly-sensitive direct labeling alternative to radioactive probes.

Features and Benefits

  • Reactive groups: NHS ester and psoralen
  • Reactive toward: amino groups and thymine
  • DNA intercalating agent and nucleic acid probe1,2
  • Reagent for photo-immobilization to microplates3
  • Melting point: 177-178°C

Caution

This product is sensitive to moisture. The vial is packaged in a resealable bag with a desiccant to reduce exposure to moisture. After cold storage, equilibrate the vial to room temperature before opening to reduce condensation inside the vial. Make fresh solutions. Storage of stock solutions is not recommended. After use, return the vial to the resealable bag. Close the bag and store the product at the recommended temperature.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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A Oser et al.
Nucleic acids research, 16(3), 1181-1196 (1988-02-11)
A new labelling method for cloned DNA probes used in hybridization assays is described. The DNA insert of recombinant plasmid DNA was made partially single-stranded for the labelling reaction by a restriction enzyme digest, followed by a controlled exonuclease III
Psoralen photochemistry.
B J Parsons
Photochemistry and photobiology, 32(6), 813-821 (1980-12-01)
Psoralen crosslinking of small RNAs in vitro.
D A Wassarman
Molecular biology reports, 17(2), 143-151 (1993-02-01)
J D Laskin et al.
Proceedings of the National Academy of Sciences of the United States of America, 83(21), 8211-8215 (1986-11-01)
The psoralens, when activated by ultraviolet light of 320-400 nm (UVA light), are potent modulators of epidermal cell growth and differentiation. Previously, we reported that, in mammalian cells, these compounds bind to specific saturable high-affinity cellular receptor sites. In the

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