Synthesis of heteroatom substituted naphthoporphyrazine derivatives with near-infrared absorption and emission

Evan R. Trivedi; Sangwan Lee; Hong Zong; Carl M. Blumenfeld; Anthony G.M. Barrett; Brian M Hoffman

doi:10.1021/jo9026947

Synthesis of heteroatom substituted naphthoporphyrazine derivatives with near-infrared absorption and emission

Evan R. Trivedi, Sangwan Lee, Hong Zong, Carl M. Blumenfeld, Anthony G.M. Barrett, Brian M Hoffman

Chemistry

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

14 Scopus citations

Abstract

"Chemical equation presented" In an effort to develop effective new optical contrast agents, we report the synthesis of porphyrazines (pzs) of the form H₂[pz(A_4-n;C_n)], n = 1, and 2 (trans-), where "A" represents peripheral heteroatom (S- and O-) Rgroups and "C" is a fused, β,β′-diisopropyloxynapntho group. The sulfide appended trans-H₂[pz(A₂;C ₂)] pz (7) has the longest wavelength absorption, ∼874 nm (log ε= 4.53), and S₁ fluorescence at ∼927 nm, wavelengths within the window of maximum tissue penetration. Emission from the oxygen-atom appended naphtho-pzs (8, 9) has been observed within carcinoma cells, confirming cellular uptake and their potential use as optical agents.

Original language	English (US)
Pages (from-to)	1799-1802
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	75
Issue number	5
DOIs	https://doi.org/10.1021/jo9026947
State	Published - Mar 5 2010

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo9026947

Cite this

@article{aae21648ded04344b12eed839ea26725,

title = "Synthesis of heteroatom substituted naphthoporphyrazine derivatives with near-infrared absorption and emission",

abstract = "{"}Chemical equation presented{"} In an effort to develop effective new optical contrast agents, we report the synthesis of porphyrazines (pzs) of the form H2[pz(A4-n;Cn)], n = 1, and 2 (trans-), where {"}A{"} represents peripheral heteroatom (S- and O-) Rgroups and {"}C{"} is a fused, β,β′-diisopropyloxynapntho group. The sulfide appended trans-H2[pz(A2;C 2)] pz (7) has the longest wavelength absorption, ∼874 nm (log ε= 4.53), and S1 fluorescence at ∼927 nm, wavelengths within the window of maximum tissue penetration. Emission from the oxygen-atom appended naphtho-pzs (8, 9) has been observed within carcinoma cells, confirming cellular uptake and their potential use as optical agents.",

author = "Trivedi, {Evan R.} and Sangwan Lee and Hong Zong and Blumenfeld, {Carl M.} and Barrett, {Anthony G.M.} and Hoffman, {Brian M}",

year = "2010",

month = mar,

day = "5",

doi = "10.1021/jo9026947",

language = "English (US)",

volume = "75",

pages = "1799--1802",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Synthesis of heteroatom substituted naphthoporphyrazine derivatives with near-infrared absorption and emission

AU - Trivedi, Evan R.

AU - Lee, Sangwan

AU - Zong, Hong

AU - Blumenfeld, Carl M.

AU - Barrett, Anthony G.M.

AU - Hoffman, Brian M

PY - 2010/3/5

Y1 - 2010/3/5

N2 - "Chemical equation presented" In an effort to develop effective new optical contrast agents, we report the synthesis of porphyrazines (pzs) of the form H2[pz(A4-n;Cn)], n = 1, and 2 (trans-), where "A" represents peripheral heteroatom (S- and O-) Rgroups and "C" is a fused, β,β′-diisopropyloxynapntho group. The sulfide appended trans-H2[pz(A2;C 2)] pz (7) has the longest wavelength absorption, ∼874 nm (log ε= 4.53), and S1 fluorescence at ∼927 nm, wavelengths within the window of maximum tissue penetration. Emission from the oxygen-atom appended naphtho-pzs (8, 9) has been observed within carcinoma cells, confirming cellular uptake and their potential use as optical agents.

AB - "Chemical equation presented" In an effort to develop effective new optical contrast agents, we report the synthesis of porphyrazines (pzs) of the form H2[pz(A4-n;Cn)], n = 1, and 2 (trans-), where "A" represents peripheral heteroatom (S- and O-) Rgroups and "C" is a fused, β,β′-diisopropyloxynapntho group. The sulfide appended trans-H2[pz(A2;C 2)] pz (7) has the longest wavelength absorption, ∼874 nm (log ε= 4.53), and S1 fluorescence at ∼927 nm, wavelengths within the window of maximum tissue penetration. Emission from the oxygen-atom appended naphtho-pzs (8, 9) has been observed within carcinoma cells, confirming cellular uptake and their potential use as optical agents.

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U2 - 10.1021/jo9026947

DO - 10.1021/jo9026947

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SN - 0022-3263

VL - 75

SP - 1799

EP - 1802

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

Synthesis of heteroatom substituted naphthoporphyrazine derivatives with near-infrared absorption and emission

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CCDC 812181: Experimental Crystal Structure Determination

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Synthesis of heteroatom substituted naphthoporphyrazine derivatives with near-infrared absorption and emission

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CCDC 812181: Experimental Crystal Structure Determination

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