US 9,808,538 B2
PSMA-targeted NIR dyes and their uses
Sumith A. Kularatne, West Lafayette, IN (US); Philip S. Low, West Lafayette, IN (US); Pravin Gagare, West Lafayette, IN (US); and Carrie Myers, Chesterfield, MO (US)
Assigned to On Target Laboratories, LLC, West Lafayette, IN (US)
Filed by On Target Laboratories, LLC, West Lafayette, IN (US)
Filed on Nov. 10, 2015, as Appl. No. 14/937,169.
Claims priority of provisional application 62/216,157, filed on Sep. 9, 2015.
Prior Publication US 2017/0065729 A1, Mar. 9, 2017
This patent is subject to a terminal disclaimer.
Int. Cl. A61B 5/00 (2006.01); A61B 8/00 (2006.01); A61B 10/00 (2006.01); A61K 49/00 (2006.01); C07D 209/20 (2006.01); C07K 5/062 (2006.01); C07K 5/083 (2006.01); G01N 21/64 (2006.01); G01N 33/574 (2006.01); C07K 5/087 (2006.01); C07K 5/11 (2006.01); C07K 7/06 (2006.01); C07K 5/09 (2006.01); C07K 5/078 (2006.01); C07K 5/065 (2006.01); C07K 5/072 (2006.01); A61K 49/16 (2006.01)
CPC A61K 49/0052 (2013.01) [A61K 49/0032 (2013.01); A61K 49/0056 (2013.01); C07D 209/20 (2013.01); C07K 5/0606 (2013.01); C07K 5/06026 (2013.01); C07K 5/06078 (2013.01); C07K 5/06095 (2013.01); C07K 5/06121 (2013.01); C07K 5/06147 (2013.01); C07K 5/06156 (2013.01); C07K 5/0806 (2013.01); C07K 5/0812 (2013.01); C07K 5/0817 (2013.01); C07K 5/1019 (2013.01); C07K 7/06 (2013.01); G01N 21/6428 (2013.01); G01N 33/57492 (2013.01); A61K 49/16 (2013.01); C12Y 304/17021 (2013.01); G01N 2021/6439 (2013.01); G01N 2333/948 (2013.01)] 7 Claims
 
1. A method of optical imaging of a biological tissue that expresses PSMA, the method comprising:
(a) contacting the biological tissue with a composition a compound having the formula: B—X—Y—Z, wherein
B comprises a compound capable of binding to prostate specific membrane antigen (PSMA),
X, is selected from the group consisting of polyethylene glycol (PEG), N-amino-dPEG2-acid and polyethylene amine (PEA),
Y comprises at least one amino acid, or derivative thereof, and
Z comprises a near-infra red (NIR) dye,
(b) allowing time for the compound in the composition to distribute within the biological target;
(c) illuminating the tissue with an excitation light of a wavelength absorbable by the compound; and
(d) detecting the optical signal emitted by the compound.