#chiralpedia

Chirality and You: Understanding and Appreciating Molecular Handedness

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Lead Chirality, or molecular handedness, is a fundamental concept in chemistry and biology that affects many aspects of our daily lives. From the structure of DNA to the effectiveness of medications, chirality plays a crucial role in how molecules interact and function. This blog aims to make the concept of chirality accessible and relevant, encouraging readers to appreciate the hidden handedness around and within them and explore the fascinating world of molecular chirality and chiral …

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Introduction to Chirality: Understanding the Basics

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Lead Chirality, derived from the Greek word “cheir” meaning hand, is a fundamental concept in chemistry that describes an object’s property of being non-superimposable on its mirror image. This property is not just an abstract mathematical idea but has profound implications in various scientific fields, particularly chemistry and biology. Understanding chirality is essential for comprehending molecular interactions and their impacts on our daily lives. This first of this blog series delves into the definition, historical …

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Protein-based CSPs

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Lead Proteins are complex, high-MW biopolymers composed of L-amino acids and possess ordered 3D-structure. They are known to bind /interact  stereoselectively with small molecules  reversibly, making them extremely versatile CSPs for chiral separation of drug molecules.   Number of CSPs has been developed by immobilizing proteins. These type of CSPs operate under RP-mode; (phosphate buffer and organic modifiers)   Characteristics of proteins used in commercial CSPs Mechanism Protein polymer remains in twisted form because of the …

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Rediscovery of stereochemistry

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Stereochemistry, in particular chirality, is known to us as early as 1809, when Malus, Arago and Biot discovered plane polarized light and its characteristics. It is observed that during 1950s to the 1970s, the “Golden Age” of drug discovery & development, stereochemistry was largely ignored resulting in approximately 57% of pharmaceuticals being marketed as racemates by the 1980s. Before going further let us examine the stereospecific awareness level that existed during 1980s’. Stereospecific Awareness level  …

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Levamisole

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Levamisole is used as anthelmintic agent to get rid of the intestinal worms. It is (S)-(-)-enantiomer of tetramisole. This drug is used in veterinary to treat hookworm infections.  Levamisole also finds therapeutic application in the treatment of colon cancer when given in conjunction with fluorouracil.   Chirality and biological activity Tetramisole carries one chiral stereogenic center and exists as an enantiomeric pair. The anthelmintic activity resides in the (S)-(-)-enantiomer, levamisole. The (R)- isomer harbors undesirable …

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Beta-Blockers

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Beta blockers, also spelled β-blockers, used as antihypertensive agents (lowering blood pressure), represent a class of chiral drugs that are marketed as racemates since the distomer exhibits no undesirable adverse effects. Three most important β-blockers viz. propranolol, atenolol, and metoprolol are marketed as racemic mixture. Chirality and biological activity β-blockers are aryloxy propanolamines with one stereogenic center and exists as a pair of enantiomers. It is observed that their therapeutic effect resides entirely in the (S)-enantiomer …

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L-Dopa

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Levodopa, L-Dopa, belong to a class of medications called dopamine agonists.  L-Dopa is used to increase dopamine concentrations in the treatment of  Parkinson’s disease. Most commonly, clinicians use levodopa as a dopamine replacement agent for the treatment of Parkinson disease. L-dopa is the precursor to dopamine and crosses the blood-brain barrier to increase dopamine neurotransmission. Chirality and Biological activity L-dopa, the (S)-enantiomer, is a chiral drug with one stereogenic center. It exists as a pair of enantiomers. The initial use …

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Terodiline

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(±)-Terodiline, the antianginal agent, perhaps represents the best authenticated example of a drug that had to be withdrawn from the world market as consequence of proven stereospecific toxicity. Terodiline has a close similarity to prenylamine from a structural and pharmacological view point. It was firs marketed as an antianginal agent but it exhibited urinary retention as a frequent and worrying side-effect. It was decided to exploit the the side-effect. Therefore the drug was redeveloped and …

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Prenylamine

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(±)-Prenylamine, an antianginal agent, was introduced in the market since early 1960. Reports associating Prenylamine with prolongation of the QT interval, ventricular tachycardia, and ventricular fibrillation started to appear. Some of these events had a fatal outcome and the drug was withdrawn from the market world-wide in 1988.  Chirality and drug withdrawals Prenylamine is chemically diphenyl-propyl derivative of phenylalkylamine. The drug is optically active with one stereogenic center (indicated by a red arrows), giving rise …

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Dilevalol

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Dilevalol is the (R,R)-diastereoisomer of labetalol. Labetalol has been in clinical use since 1977 for the treatment of hypertension.  Labetalol is an adrenergic antagonist used to treat high blood pressure. It has a role as an antihypertensive agent, a sympatholytic agent, an alpha-adrenergic antagonist and a beta-adrenergic antagonist. Chirality and drug withdrawals Labetalol has two stereogenic centers and consequently exists as four stereoisomers. It is a diastereoisomeric mixture of approximately equal amounts of all four possible stereoisomers …

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