Analyte-Induced Restriction of Intramolecular Rotation: Turn-On aza-BODIPY Sensor for Biothiol Detection in Aqueous Media

Bleda Can Sadikogullari; Ayse Daut Ozdemir

doi:10.1021/acs.orglett.5c02543

Analyte-Induced Restriction of Intramolecular Rotation: Turn-On aza-BODIPY Sensor for Biothiol Detection in Aqueous Media

Bleda Can Sadikogullari
, Ayse Daut Ozdemir^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

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

3 Citations (Scopus)

Abstract

Two alternate aza-BODIPY fluorophores bearing a formyl-functional group were synthesized and evaluated for biothiol sensing. Both provide high binding constants (up to 9800 M^–1) and low limits of detection (as low as 1 μM). More importantly, this study introduces an unconventional “turn-on” sensing mechanism, in which fluorescence enhancement arises from analyte-induced restriction of intramolecular rotation rather than analyte-triggered cleavage of quencher. This alternative strategy provides a promising platform for the development of next-generation fluorescent probes.

Original language	English
Pages (from-to)	9884-9889
Number of pages	6
Journal	Organic Letters
Volume	27
Issue number	36
DOIs	https://doi.org/10.1021/acs.orglett.5c02543
Publication status	Published - 12 Sept 2025

Bibliographical note

Publisher Copyright:
© 2025 American Chemical Society

Access to Document

10.1021/acs.orglett.5c02543

Cite this

@article{2509af77cec84d1993118def3f9677f7,

title = "Analyte-Induced Restriction of Intramolecular Rotation: Turn-On aza-BODIPY Sensor for Biothiol Detection in Aqueous Media",

abstract = "Two alternate aza-BODIPY fluorophores bearing a formyl-functional group were synthesized and evaluated for biothiol sensing. Both provide high binding constants (up to 9800 M–1) and low limits of detection (as low as 1 μM). More importantly, this study introduces an unconventional “turn-on” sensing mechanism, in which fluorescence enhancement arises from analyte-induced restriction of intramolecular rotation rather than analyte-triggered cleavage of quencher. This alternative strategy provides a promising platform for the development of next-generation fluorescent probes.",

author = "Sadikogullari, \{Bleda Can\} and Ozdemir, \{Ayse Daut\}",

note = "Publisher Copyright: {\textcopyright} 2025 American Chemical Society",

year = "2025",

month = sep,

day = "12",

doi = "10.1021/acs.orglett.5c02543",

language = "English",

volume = "27",

pages = "9884--9889",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "36",

}

TY - JOUR

T1 - Analyte-Induced Restriction of Intramolecular Rotation

T2 - Turn-On aza-BODIPY Sensor for Biothiol Detection in Aqueous Media

AU - Sadikogullari, Bleda Can

AU - Ozdemir, Ayse Daut

PY - 2025/9/12

Y1 - 2025/9/12

N2 - Two alternate aza-BODIPY fluorophores bearing a formyl-functional group were synthesized and evaluated for biothiol sensing. Both provide high binding constants (up to 9800 M–1) and low limits of detection (as low as 1 μM). More importantly, this study introduces an unconventional “turn-on” sensing mechanism, in which fluorescence enhancement arises from analyte-induced restriction of intramolecular rotation rather than analyte-triggered cleavage of quencher. This alternative strategy provides a promising platform for the development of next-generation fluorescent probes.

AB - Two alternate aza-BODIPY fluorophores bearing a formyl-functional group were synthesized and evaluated for biothiol sensing. Both provide high binding constants (up to 9800 M–1) and low limits of detection (as low as 1 μM). More importantly, this study introduces an unconventional “turn-on” sensing mechanism, in which fluorescence enhancement arises from analyte-induced restriction of intramolecular rotation rather than analyte-triggered cleavage of quencher. This alternative strategy provides a promising platform for the development of next-generation fluorescent probes.

UR - https://www.scopus.com/pages/publications/105015686790

U2 - 10.1021/acs.orglett.5c02543

DO - 10.1021/acs.orglett.5c02543

M3 - Letter

C2 - 40866077

AN - SCOPUS:105015686790

SN - 1523-7060

VL - 27

SP - 9884

EP - 9889

JO - Organic Letters

JF - Organic Letters

IS - 36

ER -

Analyte-Induced Restriction of Intramolecular Rotation: Turn-On aza-BODIPY Sensor for Biothiol Detection in Aqueous Media

Abstract

Bibliographical note

Access to Document

Other files and links

Fingerprint

Cite this