کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5371458 1388822 2011 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Intramolecular hydrogen bonding in articaine can be related to superior bone tissue penetration: A molecular dynamics study
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی تئوریک و عملی
پیش نمایش صفحه اول مقاله
Intramolecular hydrogen bonding in articaine can be related to superior bone tissue penetration: A molecular dynamics study
چکیده انگلیسی

Local anesthetics (LAs) are drugs that cause reversible loss of nociception during surgical procedures. Articaine is a commonly used LA in dentistry that has proven to be exceptionally effective in penetrating bone tissue and induce anesthesia on posterior teeth in maxilla and mandibula. In the present study, our aim was to gain a deeper understanding of the penetration of articaine through biological membranes by studying the interactions of articaine with a phospholipid membrane. Our approach involves Langmuir monolayer experiments combined with molecular dynamics simulations. Membrane permeability of LAs can be modulated by pH due to a titratable amine group with a pKa value close to physiological pH. A change in protonation state is thus known to act as a lipophilicity switch in LAs. Our study shows that articaine has an additional unique lipophilicity switch in its ability to form an intramolecular hydrogen bond. We suggest this intramolecular hydrogen bond as a novel and additional solvent-dependent mechanism for modulation of lipophilicity of articaine which may enhance its diffusion through membranes and connective tissue.

Graphical AbstractResearch Highlights► Internal hydrogen bond in articaine. ► Increased lipophilicity. ► Superior membrane penetration. ► Increased anesthetic efficacy.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Biophysical Chemistry - Volume 154, Issue 1, February 2011, Pages 18-25
نویسندگان
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