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Issue 103, 2015
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Orosomucoid binding induced amplification of inherent chirality of the immunosuppressant drug sirolimus

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Abstract

Circular dichroism (CD) spectroscopic data indicate the conformational change of the triene moiety of the immunosuppressive agent sirolimus (rapamycin) upon its binding to human α1-acid glycoprotein (orosomucoid). The development of an intense, negative π → π* CD Cotton effect and the bathochromic shift of the corresponding UV band are attributed to the increased helical distortion of the conjugated π-system. Comparative chiroptical evaluation of the interaction of sirolimus with the separated genetic variants of orosomucoid suggests that the F1/S form is dominant in the amplification of inherent chirality of the triene chromophore while the A variant induces much weaker structural modification. Consistently, the drug binding affinities of the native protein and the F1/S variant estimated from the CD spectra are close to each other (∼2 × 105 M−1).

Graphical abstract: Orosomucoid binding induced amplification of inherent chirality of the immunosuppressant drug sirolimus

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Publication details

The article was received on 22 Jul 2015, accepted on 28 Sep 2015 and first published on 06 Oct 2015


Article type: Communication
DOI: 10.1039/C5RA14546E
Citation: RSC Adv., 2015,5, 84523-84525

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    Orosomucoid binding induced amplification of inherent chirality of the immunosuppressant drug sirolimus

    F. Zsila, RSC Adv., 2015, 5, 84523
    DOI: 10.1039/C5RA14546E

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