For research use only. Not for therapeutic Use.
CRANAD-2 is a difluoroboron-derivatized curcumins as near-infrared probe for in vivo detection of amyloid-beta deposits. Upon interacting with Abeta aggregates, CRANAD-2 undergoes a range of changes, which include a 70-fold fluorescence intensity increase, a 90 nm blue shift (from 805 to 715 nm), and a large increase in quantum yield. Moreover, this probe also shows a high affinity for Abeta aggregates (K(d) = 38.0 nM), a reasonable log P value (log P = 3), considerable stability in serum, and a weak interaction with albumin. After intravenous injection of this probe, 19-month-old Tg2576 mice exhibited significantly higher relative signal than that of the control mice over the same period of time.
| Catalog Number | R061912 |
| CAS Number | 1193447-34-5 |
| Synonyms | (T-4)-[(1E,6E)-1,7-Bis[4-(dimethylamino)phenyl]-1,6-heptadiene-3,5-dionato-κO3,κO5]difluoro-boron |
| Molecular Formula | C23H25BF2N2O2 |
| Purity | ≥95% |
| Target | Amyloid-β |
| Solubility | Limited solubility |
| Storage | Store at -20C |
| IUPAC Name | [4-[(2Z)-2-[6-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]-2,2-difluoro-1,3-dioxa-2-boranuidacyclohex-5-en-4-ylidene]ethylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium |
| InChI | InChI=1S/C23H25BF2N2O2/c1-27(2)20-11-5-18(6-12-20)9-15-22-17-23(30-24(25,26)29-22)16-10-19-7-13-21(14-8-19)28(3)4/h5-17H,1-4H3 |
| InChIKey | PVXQJYXODFZTBR-UHFFFAOYSA-N |
| SMILES | [B-]1(OC(=CC(=CC=C2C=CC(=[N+](C)C)C=C2)O1)C=CC3=CC=C(C=C3)N(C)C)(F)F |
| Reference | </br>1: Leung K. 5-(2E,4E)-5-(6-hydroxy-4-oxo-2-thioxo-1,2,3,4-tetrahydroxy-5</br> pyrimidinyl)-2,4-pentadienylidene-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione.</br> 2012 Jul 01 [updated 2012 Oct 25]. Molecular Imaging and Contrast Agent Database </br> (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information </br> (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK109729/</br> PubMed PMID: 23115807.</br>2: Bertoncini CW, Celej MS. Small molecule fluorescent probes for the detection</br> of amyloid self-assembly in vitro and in vivo. Curr Protein Pept Sci. 2011</br> May;12(3):205-20. Review. PubMed PMID: 21348839.</br>3: Ran C, Xu X, Raymond SB, Ferrara BJ, Neal K, Bacskai BJ, Medarova Z, Moore A. </br> Design, synthesis, and testing of difluoroboron-derivatized curcumins as</br> near-infrared probes for in vivo detection of amyloid-beta deposits. J Am Chem</br> Soc. 2009 Oct 28;131(42):15257-61. doi: 10.1021/ja9047043. PubMed PMID: 19807070;</br> PubMed Central PMCID: PMC2784241.</br> </br> |
