N-alkylated aminopyrazines for use as hydrophilic optical agents

Amruta R. Poreddy; Bethel Asmelash; Karen P. Galen; Richard M. Fitch; Jeng-Jong Shieh; James M. Wilcox; Tasha M. Schoenstein; Jolette K. Wojdyla; Kimberly R. Gaston; John N. Freskos; William L. Neumann; Raghavan Rajagopalan; Hyo-Yang Ahn; James G. Kostelc; Martin P. Debreczeny; Kevin D. Belfield; Richard B. Dorshow

doi:10.1117/12.809287

20 February 2009 N-alkylated aminopyrazines for use as hydrophilic optical agents

Amruta R. Poreddy, Bethel Asmelash, Karen P. Galen, Richard M. Fitch, Jeng-Jong Shieh, James M. Wilcox, Tasha M. Schoenstein, Jolette K. Wojdyla, Kimberly R. Gaston, John N. Freskos, William L. Neumann, Raghavan Rajagopalan, Hyo-Yang Ahn, James G. Kostelc, Martin P. Debreczeny, Kevin D. Belfield, Richard B. Dorshow

Author Affiliations +

Proceedings Volume 7190, Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications; 71900P (2009) https://doi.org/10.1117/12.809287
Event: SPIE BiOS, 2009, San Jose, California, United States

Abstract

Rapid assessment of glomerular filtration rate (GFR), which measures the amount of plasma filtered through the kidney within a given time, would greatly facilitate monitoring of renal function for patients at the bedside in the clinic. In our pursuit to develop exogenous fluorescent tracers for real-time monitoring of renal function by optical methods, N-alkylated aminopyrazine dyes and their hydrophilic conjugates based on poly (ethylene glycol) (PEG) were synthesized via reductive amination as the key step. Photophysical properties indicated a bathochromic shift on the order of 50 nm in both absorption and emission compared to naked aminopyrazines which could be very useful in enhancing both tissue penetration as well as easier detection methods. Structure-activity relationship (SAR) and pharmacokinetic (PK) studies, and the correlation of in vivo optical data with plasma PK for measurement of clearance (and hence GFR) are focus of the current investigation.

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Amruta R. Poreddy, Bethel Asmelash, Karen P. Galen, Richard M. Fitch, Jeng-Jong Shieh, James M. Wilcox, Tasha M. Schoenstein, Jolette K. Wojdyla, Kimberly R. Gaston, John N. Freskos, William L. Neumann, Raghavan Rajagopalan, Hyo-Yang Ahn, James G. Kostelc, Martin P. Debreczeny, Kevin D. Belfield, and Richard B. Dorshow "N-alkylated aminopyrazines for use as hydrophilic optical agents", Proc. SPIE 7190, Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications, 71900P (20 February 2009); https://doi.org/10.1117/12.809287

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