Fluorescence quenching properties of copper(II) ions have been used for designing Cu(II) sensitive fluorescent molecular probes. In this paper, we demonstrate that static quenching plays a key role in free Cu(II)-mediated fluorescence quenching of a near infrared (NIR) fluorescent dye cypate. The Stern-Volmer quenching constant was calculated to be KSV = 970,000 M-1 in 25 mM MES buffer, pH 6.5 at room temperature. We synthesized LS835, a compound containing cypate attached covalently to chelated Cu(II) to study fluorescence quenching by chelated Cu(II). The fluorescence quenching mechanism of chelated Cu(II) is predominantly dynamic or collisional quenching. The quenching efficiency of chelated Cu(II) was calculated to be 58% ± 6% in dimethylsulfoxide at room temperature. Future work will involve further characterization of the mechanism of NIR fluorescence quenching by Cu(II) and testing its reversibility for potential applications in designing fluorophore-quencher based molecular probes for biological imaging.