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Related Concept Videos

Chirality in Nature02:30

Chirality in Nature

16.4K
Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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Chirality02:25

Chirality

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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
14.7K
Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Related Experiment Video

Updated: Jan 4, 2026

Fabrication of Spherical and Worm-shaped Micellar Nanocrystals by Combining Electrospray, Self-assembly, and Solvent-based Structure Control
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Chiral Supraparticles for Controllable Nanomedicine.

Jihyeon Yeom1, Pedro P G Guimaraes1,2, Hyo Min Ahn3

  • 1David H. Koch Institute for Integrative Cancer Research, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA.

Advanced Materials (Deerfield Beach, Fla.)
|November 6, 2019
PubMed
Summary

Chiral-engineered nanoparticles with d-chirality show enhanced cancer cell uptake and longer circulation times. This chirality-dependent interaction offers new possibilities for biomaterials in medicine.

Keywords:
chiralitydrug delivery systemsnanomedicineself-assemblysupraparticles

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Area of Science:

  • Biomaterials Science
  • Nanotechnology
  • Cell Biology

Background:

  • Chirality is fundamental to biological systems.
  • Controlling biomaterial chirality for cellular interactions is an emerging field.
  • Chiral-engineered supraparticles (SPs) offer a platform to study chirality-dependent biological interactions.

Purpose of the Study:

  • To investigate the differential interactions of chiral-engineered supraparticles (SPs) with cancer cells.
  • To elucidate the mechanism behind chirality-specific cellular uptake and in vivo stability.
  • To explore the potential of chiral nanosystems in biomedical applications.

Main Methods:

  • Synthesis of chiral-engineered supraparticles (SPs) with defined handedness (d- and l-chirality).
  • Assessment of cell membrane penetration using breast, cervical, and multiple myeloma cancer cell lines.
  • Mechanism elucidation using Quartz Crystal Microbalance with Dissipation (QCM-D) and Isothermal Titration Calorimetry (ITC).
  • Evaluation of in vivo stability and biological half-life.

Main Results:

  • SPs with d-chirality demonstrated over threefold enhanced cell membrane penetration in multiple cancer cell lines.
  • d-SPs exhibited more stable adhesion to lipid bilayers compared to l-SPs, explained by thermodynamic analysis.
  • In vivo studies showed superior stability and longer biological half-lives for d-SPs, attributed to protection from endogenous proteins.

Conclusions:

  • Incorporating d-chirality into nanosystems significantly enhances cancer cell uptake and prolongs in vivo circulation stability.
  • Chirality is a critical factor in biomaterial design for improved therapeutic and diagnostic applications.
  • Chiral nanosystems hold promise for advanced drug delivery, tumor detection, and biosensing.