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[ CAS No. 58656-04-5 ] {[proInfo.proName]}

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Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
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Chemical Structure| 58656-04-5
Chemical Structure| 58656-04-5
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Product Citations

Product Citations

William E. Meador ; Timothy A. Lewis ; Abdul K. Shaik , et al. DOI:

Abstract: Fluorescence-based biological imaging in the shortwave infrared (SWIR, 1000–1700 nm) is an attractive replacement for modern in vivo imaging techniques currently employed in both medical and research settings. Xanthene-based fluorophores containing heterocycle donors have recently emerged as a way to access deep SWIR emitting fluorophores. A concern for xanthene-based SWIR fluorophores though is chemical stability toward ambient nucleophiles due to the high electrophilicity of the cationic fluorophore core. Herein, a series of SWIR emitting silicon-rosindolizine (SiRos) fluorophores with emission maxima >1300 nm (up to 1550 nm) are synthesized. The SiRos fluorophore photophysical properties and chemical stability toward nucleophiles are examined through systematic derivatization of the silicon-core alkyl groups, indolizine donor substitution, and the use of o-tolyl or o-xylyl groups appended to the fluorophore core. The dyes are studied via absorption spectroscopy, steady-state emission spectroscopy, solution-based cyclic voltammetry, time-dependent density functional theory (TD-DFT) computational analysis, X-ray diffraction crystallography, and relative chemical stability over time. Optimal chemical stability is observed via the incorporation of the 2-ethylhexyl silicon substituent and the o-xylyl group to protect the core of the fluorophore.

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Product Details of [ 58656-04-5 ]

CAS No. :58656-04-5 MDL No. :MFCD03840580
Formula : C18H34BF4P Boiling Point : -
Linear Structure Formula :- InChI Key :MYSMMEUXKHJYKH-UHFFFAOYSA-O
M.W : 368.24 Pubchem ID :11710396
Synonyms :

Calculated chemistry of [ 58656-04-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 101.86
TPSA : 13.59 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 7.59
Log Po/w (WLOGP) : 9.18
Log Po/w (MLOGP) : 6.07
Log Po/w (SILICOS-IT) : 4.77
Consensus Log Po/w : 5.52

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.71
Solubility : 0.0000723 mg/ml ; 0.000000196 mol/l
Class : Poorly soluble
Log S (Ali) : -7.71
Solubility : 0.00000714 mg/ml ; 0.0000000194 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -4.3
Solubility : 0.0185 mg/ml ; 0.0000501 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.22

Safety of [ 58656-04-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 UN#:1759
Hazard Statements:H302-H314 Packing Group:Ⅲ
GHS Pictogram:
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