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

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

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

2 Scopus citations

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, Nalkylated 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.

Original language	English (US)
Title of host publication	Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications
DOIs	https://doi.org/10.1117/12.809287
State	Published - 2009
Externally published	Yes
Event	Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications - San Jose, CA, United States Duration: Jan 26 2009 → Jan 29 2009

Publication series

Name	Progress in Biomedical Optics and Imaging - Proceedings of SPIE
Volume	7190
ISSN (Print)	1605-7422

Other

Other	Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications
Country/Territory	United States
City	San Jose, CA
Period	1/26/09 → 1/29/09

All Science Journal Classification (ASJC) codes

Electronic, Optical and Magnetic Materials
Atomic and Molecular Physics, and Optics
Biomaterials
Radiology Nuclear Medicine and imaging

Keywords

Fluorescence
GFR
Optical monitoring
PEG
Pyrazine
Reductive amination
Renal clearnce.
Renal function

Access to Document

10.1117/12.809287

Cite this

Poreddy, A. R., Asmelash, B., Galen, K. P., Fitch, R. M., Shieh, J. J., Wilcox, J. M., Schoenstein, T. M., Wojdyla, J. K., Gaston, K. R., Freskos, J. N., Neumann, W. L., Rajagopalan, R., Ahn, H. Y., Kostelc, J. G., Debreczeny, M. P., Belfield, K. D., & Dorshow, R. B. (2009). N-Alkylated aminopyrazines for use as hydrophilic optical agents. In Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications Article 71900P (Progress in Biomedical Optics and Imaging - Proceedings of SPIE; Vol. 7190). https://doi.org/10.1117/12.809287

@inproceedings{9a10643318ca449d918f66d1d6cc3cd0,

title = "N-Alkylated aminopyrazines for use as hydrophilic optical agents",

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, Nalkylated 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.",

keywords = "Fluorescence, GFR, Optical monitoring, PEG, Pyrazine, Reductive amination, Renal clearnce., Renal function",

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

year = "2009",

doi = "10.1117/12.809287",

language = "English (US)",

isbn = "9780819474360",

series = "Progress in Biomedical Optics and Imaging - Proceedings of SPIE",

booktitle = "Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications",

note = "Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications ; Conference date: 26-01-2009 Through 29-01-2009",

}

Poreddy, AR, Asmelash, B, Galen, KP, Fitch, RM, Shieh, JJ, Wilcox, JM, Schoenstein, TM, Wojdyla, JK, Gaston, KR, Freskos, JN, Neumann, WL, Rajagopalan, R, Ahn, HY, Kostelc, JG, Debreczeny, MP, Belfield, KD & Dorshow, RB 2009, N-Alkylated aminopyrazines for use as hydrophilic optical agents. in Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications., 71900P, Progress in Biomedical Optics and Imaging - Proceedings of SPIE, vol. 7190, Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications, San Jose, CA, United States, 1/26/09. https://doi.org/10.1117/12.809287

N-Alkylated aminopyrazines for use as hydrophilic optical agents. / Poreddy, Amruta R.; Asmelash, Bethel; Galen, Karen P. et al.
Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications. 2009. 71900P (Progress in Biomedical Optics and Imaging - Proceedings of SPIE; Vol. 7190).

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

TY - GEN

T1 - N-Alkylated aminopyrazines for use as hydrophilic optical agents

AU - Poreddy, Amruta R.

AU - Asmelash, Bethel

AU - Galen, Karen P.

AU - Fitch, Richard M.

AU - Shieh, Jeng Jong

AU - Wilcox, James M.

AU - Schoenstein, Tasha M.

AU - Wojdyla, Jolette K.

AU - Gaston, Kimberly R.

AU - Freskos, John N.

AU - Neumann, William L.

AU - Rajagopalan, Raghavan

AU - Ahn, Hyo Yang

AU - Kostelc, James G.

AU - Debreczeny, Martin P.

AU - Belfield, Kevin D.

AU - Dorshow, Richard B.

PY - 2009

Y1 - 2009

N2 - 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, Nalkylated 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.

AB - 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, Nalkylated 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.

KW - Fluorescence

KW - GFR

KW - Optical monitoring

KW - PEG

KW - Pyrazine

KW - Reductive amination

KW - Renal clearnce.

KW - Renal function

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U2 - 10.1117/12.809287

DO - 10.1117/12.809287

M3 - Conference contribution

AN - SCOPUS:66749105829

SN - 9780819474360

T3 - Progress in Biomedical Optics and Imaging - Proceedings of SPIE

BT - Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications

T2 - Reporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications

Y2 - 26 January 2009 through 29 January 2009

ER -

N-Alkylated aminopyrazines for use as hydrophilic optical agents

Abstract

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All Science Journal Classification (ASJC) codes

Keywords

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