Discovery of new photoactivatable diaryltetrazoles for photoclick chemistry via scaffold hopping

Zhipeng Yu; Lok Yin Ho; Zhiyong Wang; Qing Lin

doi:10.1016/j.bmcl.2011.04.087

Discovery of new photoactivatable diaryltetrazoles for photoclick chemistry via scaffold hopping

Zhipeng Yu
, Lok Yin Ho
, Zhiyong Wang
, Qing Lin

Chemistry

SUNY Buffalo

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

54 Scopus citations

Abstract

We report the discovery of two long-wavelength (365 nm) photoactivatable diaryltetrazoles through screening a small library of diaryltetrazoles that were designed using a 'scaffold hopping' strategy. A naphthalene-derived tetrazole showed excellent reactivity in the photoinduced cycloaddition reaction with methyl methacrylate under 365 nm photoirradiation in acetonitrile PBS buffer mixture. Besides, the brightly fluorescent pyrazoline cycloadducts that were formed further increase the potential utility of these new diaryltetrazoles as 'photoclick' reagents and as reporters in biological studies.

Original language	English
Pages (from-to)	5033-5036
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	17
DOIs	https://doi.org/10.1016/j.bmcl.2011.04.087
State	Published - Sep 1 2011

Keywords

Bioorthogonal chemistry
Dipolar cycloaddition
Fluorophores
Photoclick chemistry
Tetrazoles

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10.1016/j.bmcl.2011.04.087

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title = "Discovery of new photoactivatable diaryltetrazoles for photoclick chemistry via scaffold hopping",

abstract = "We report the discovery of two long-wavelength (365 nm) photoactivatable diaryltetrazoles through screening a small library of diaryltetrazoles that were designed using a 'scaffold hopping' strategy. A naphthalene-derived tetrazole showed excellent reactivity in the photoinduced cycloaddition reaction with methyl methacrylate under 365 nm photoirradiation in acetonitrile PBS buffer mixture. Besides, the brightly fluorescent pyrazoline cycloadducts that were formed further increase the potential utility of these new diaryltetrazoles as 'photoclick' reagents and as reporters in biological studies.",

keywords = "Bioorthogonal chemistry, Dipolar cycloaddition, Fluorophores, Photoclick chemistry, Tetrazoles",

author = "Zhipeng Yu and Ho, \{Lok Yin\} and Zhiyong Wang and Qing Lin",

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AU - Yu, Zhipeng

AU - Ho, Lok Yin

AU - Wang, Zhiyong

AU - Lin, Qing

PY - 2011/9/1

Y1 - 2011/9/1

N2 - We report the discovery of two long-wavelength (365 nm) photoactivatable diaryltetrazoles through screening a small library of diaryltetrazoles that were designed using a 'scaffold hopping' strategy. A naphthalene-derived tetrazole showed excellent reactivity in the photoinduced cycloaddition reaction with methyl methacrylate under 365 nm photoirradiation in acetonitrile PBS buffer mixture. Besides, the brightly fluorescent pyrazoline cycloadducts that were formed further increase the potential utility of these new diaryltetrazoles as 'photoclick' reagents and as reporters in biological studies.

AB - We report the discovery of two long-wavelength (365 nm) photoactivatable diaryltetrazoles through screening a small library of diaryltetrazoles that were designed using a 'scaffold hopping' strategy. A naphthalene-derived tetrazole showed excellent reactivity in the photoinduced cycloaddition reaction with methyl methacrylate under 365 nm photoirradiation in acetonitrile PBS buffer mixture. Besides, the brightly fluorescent pyrazoline cycloadducts that were formed further increase the potential utility of these new diaryltetrazoles as 'photoclick' reagents and as reporters in biological studies.

KW - Bioorthogonal chemistry

KW - Dipolar cycloaddition

KW - Fluorophores

KW - Photoclick chemistry

KW - Tetrazoles

UR - https://www.scopus.com/pages/publications/80051789999

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M3 - Article

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AN - SCOPUS:80051789999

SN - 0960-894X

VL - 21

SP - 5033

EP - 5036

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 17

ER -

Discovery of new photoactivatable diaryltetrazoles for photoclick chemistry via scaffold hopping

Abstract

Keywords

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