Toward Optimal Ru(II) Photocages: Balancing Photochemistry, Stability, and Biocompatibility through Fine Tuning of Steric, Electronic, and Physiochemical Features

Dmytro Havrylyuk; Kimberly Stevens; Sean Parkin; Edith C. Glazer

doi:10.1021/acs.inorgchem.9b02065

Toward Optimal Ru(II) Photocages: Balancing Photochemistry, Stability, and Biocompatibility through Fine Tuning of Steric, Electronic, and Physiochemical Features

Dmytro Havrylyuk, Kimberly Stevens, Sean Parkin, Edith C. Glazer

Chemistry

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

Abstract

Ru(II) complex photocages are used in a variety of biological applications, but the thermal stability, photosubstitution quantum yield, and biological compatibility of the most commonly used Ru(II) systems remain unoptimized. Here, multiple compounds used in photocaging applications were analyzed and found to have several unsatisfactory characteristics. To address these deficiencies, three new scaffolds were designed to improve key properties through modulation of a combination of electronic, steric, and physiochemical features. One of these new systems, containing the 2,2′-biquinoline-4,4′-dicarboxylic acid (2,2′-bicinchoninic acid) ligand, fulfills several of the requirements for an optimal photocage. Another complex, containing the 2-benzothiazol-2-yl-quinoline ligand, provides a scaffold for the creation of "dual action" agents.

Original language	English
Pages (from-to)	1006-1013
Number of pages	8
Journal	Inorganic Chemistry
Volume	59
Issue number	2
DOIs	https://doi.org/10.1021/acs.inorgchem.9b02065
State	Published - Jan 21 2020

Bibliographical note

Funding Information:
We gratefully acknowledge the National Institutes of Health (Grant GM107586) for the support of this research. Crystallographic work was made possible by the National Science Foundation (NSF) MRI program, grants CHE-0319176 and CHE-1625732.

Publisher Copyright:
Copyright © 2020 American Chemical Society.

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry

Access to Document

10.1021/acs.inorgchem.9b02065

Cite this

@article{ed8899130ce147aaa72f454e228eb13d,

title = "Toward Optimal Ru(II) Photocages: Balancing Photochemistry, Stability, and Biocompatibility through Fine Tuning of Steric, Electronic, and Physiochemical Features",

abstract = "Ru(II) complex photocages are used in a variety of biological applications, but the thermal stability, photosubstitution quantum yield, and biological compatibility of the most commonly used Ru(II) systems remain unoptimized. Here, multiple compounds used in photocaging applications were analyzed and found to have several unsatisfactory characteristics. To address these deficiencies, three new scaffolds were designed to improve key properties through modulation of a combination of electronic, steric, and physiochemical features. One of these new systems, containing the 2,2′-biquinoline-4,4′-dicarboxylic acid (2,2′-bicinchoninic acid) ligand, fulfills several of the requirements for an optimal photocage. Another complex, containing the 2-benzothiazol-2-yl-quinoline ligand, provides a scaffold for the creation of {"}dual action{"} agents.",

author = "Dmytro Havrylyuk and Kimberly Stevens and Sean Parkin and Glazer, {Edith C.}",

note = "Funding Information: We gratefully acknowledge the National Institutes of Health (Grant GM107586) for the support of this research. Crystallographic work was made possible by the National Science Foundation (NSF) MRI program, grants CHE-0319176 and CHE-1625732. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = jan,

day = "21",

doi = "10.1021/acs.inorgchem.9b02065",

language = "English",

volume = "59",

pages = "1006--1013",

number = "2",

}

TY - JOUR

T1 - Toward Optimal Ru(II) Photocages

T2 - Balancing Photochemistry, Stability, and Biocompatibility through Fine Tuning of Steric, Electronic, and Physiochemical Features

AU - Havrylyuk, Dmytro

AU - Stevens, Kimberly

AU - Parkin, Sean

AU - Glazer, Edith C.

N1 - Funding Information: We gratefully acknowledge the National Institutes of Health (Grant GM107586) for the support of this research. Crystallographic work was made possible by the National Science Foundation (NSF) MRI program, grants CHE-0319176 and CHE-1625732. Publisher Copyright: Copyright © 2020 American Chemical Society.

PY - 2020/1/21

Y1 - 2020/1/21

N2 - Ru(II) complex photocages are used in a variety of biological applications, but the thermal stability, photosubstitution quantum yield, and biological compatibility of the most commonly used Ru(II) systems remain unoptimized. Here, multiple compounds used in photocaging applications were analyzed and found to have several unsatisfactory characteristics. To address these deficiencies, three new scaffolds were designed to improve key properties through modulation of a combination of electronic, steric, and physiochemical features. One of these new systems, containing the 2,2′-biquinoline-4,4′-dicarboxylic acid (2,2′-bicinchoninic acid) ligand, fulfills several of the requirements for an optimal photocage. Another complex, containing the 2-benzothiazol-2-yl-quinoline ligand, provides a scaffold for the creation of "dual action" agents.

AB - Ru(II) complex photocages are used in a variety of biological applications, but the thermal stability, photosubstitution quantum yield, and biological compatibility of the most commonly used Ru(II) systems remain unoptimized. Here, multiple compounds used in photocaging applications were analyzed and found to have several unsatisfactory characteristics. To address these deficiencies, three new scaffolds were designed to improve key properties through modulation of a combination of electronic, steric, and physiochemical features. One of these new systems, containing the 2,2′-biquinoline-4,4′-dicarboxylic acid (2,2′-bicinchoninic acid) ligand, fulfills several of the requirements for an optimal photocage. Another complex, containing the 2-benzothiazol-2-yl-quinoline ligand, provides a scaffold for the creation of "dual action" agents.

UR - http://www.scopus.com/inward/record.url?scp=85078397022&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85078397022&partnerID=8YFLogxK

U2 - 10.1021/acs.inorgchem.9b02065

DO - 10.1021/acs.inorgchem.9b02065

M3 - Article

C2 - 31899619

AN - SCOPUS:85078397022

VL - 59

SP - 1006

EP - 1013

IS - 2

ER -

Toward Optimal Ru(II) Photocages: Balancing Photochemistry, Stability, and Biocompatibility through Fine Tuning of Steric, Electronic, and Physiochemical Features

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this