Synthesis of a New Cyanoacrylate Monomer and Its Application in Fluorescence Imaging in vivo†

doi:10.7503/cjcu20160079

Abstract

Abstract:

A new cyanoacrylate monomer with fluorescein isothiocyanate(FITC) labeling was synthesized. It could copolymerize with any other cyanoacrylate monomers and result in copolymer being able to produce fluorescence. Well fluorescence imaging could be got when the copolymer was embedded in subcutaneous tissue of Sprague-Dawley(SD) mice. We also discussed the degradation pattern of polycyanoacrylate by monitoring the fluorescence intensity with time. The synthesis was started with anthracene /cyanoacrylate acid adduct and 6-(4,4'-dimethoxytriphenylmethyl)-amino-1-hexanol. After deprotection of 4,4'-dimethoxytriphenylmethyl group from intermediate anthracene/6-(4,4'-dimethoxytriphenylmethyl)-amino-1-hexanol cyanoacrylate adduct, FITC was labeled onto the amino group. The target product was finally got by reduction of the ethylenic bond. Structure of intermediates and target compound were identified by ¹H NMR and MS spectroscopy. Both the monomer and polymer could be observed fluorescence around 525 nm wavelength by an exciting light at 488 nm.

Key words: Cyanoacrylate, Fluorescein isothiocyanate(FITC), Fluorescence imaging in vivo

CLC Number:

O632.1

TrendMD:

ZHANG Tao, TANG Yongjia, XU Liang, LIU Keliang. Synthesis of a New Cyanoacrylate Monomer and Its Application in Fluorescence Imaging in vivo^†[J]. Chem. J. Chinese Universities, 2016, 37(6): 1168.

Figures/Tables 7

Scheme 1 Synthesis of 6-DMT-amino-1-hexanolConditions: C3H9ClSi, pyridine, r.t., 12 h.

Scheme 2 Synthesis of FITC-labeling 6-amino-1-hexanol cyanoacrylatei. DIC, DMAP, DCM, r.t., 6 h; ii. CH3COOH, DCM, r.t.; iii. FITC, DCM, EtOH, r.t.; iv. Maleic anhydride, dimethylbenzene, EtOH, r.t., 5 h.

Fig.1 In vitro fluorescence imaging of poly(FITC-labeling cyanoacrylate)a. Control group: poly(N-butyl cyanoacrylate); b. experimental group A: poly(FITC-labeling cyanoacrylate); c. experimental group B: poly[(FITC-labeling cyanoacrylate)∶N-butyl cyanoacrylate(mass ratio=1∶5)].

Fig.2 In vivo fluorescence imaging of poly(FITC-labeling cyanoacrylate)a. Control group∶poly(N-butyl cyanoacrylate); b. experimental group: poly[(FITC-labeling cyanoacrylate)∶N-butyl cyanoacrylate(mass ratio=1∶5)].

Fig.3 In vivo fluorescence intensity test of poly(FITC-labeling cyanoarylate)(A) Fluorescence imaging; (B) fluorescence intensity.

Fig.4 Residue of poly(FITC-labeling cyanoacrylate) embedded in SD mice after 14 d

Fig.5 GPC analysis of the residual solid embedded in SD mice after 14 d(A) Poly[(FITC-labeling cyanoacrylate)∶N-butyl cyanoacrylate(mass ratio=1∶5)] before degradation; (B) residual solid of poly[(FITC-labeling cyanoacrylate)∶N-butyl cyanoacrylate(mass ratio=1∶5)] after 14 d.

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