1‐Hydroxymethyl‐7‐oxabicyclo[2.2.1]hept‐2‐ene skeleton in enantiopure form through enzymatic kinetic resolution

Reddy, U. Chandrasekhar; Manheri, Muraleedharan K.

doi:10.1002/chir.23060

Cited by 7 publications

(1 citation statement)

References 84 publications

(109 reference statements)

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“…We investigated the enzyme-assisted interfacial regioselective ester hydrolysis of synthetic ONB-based amphiphiles . Moreover, our research explored lipase-catalyzed acetylation and deacetylation processes aimed at achieving the enantiopure form of the ONB headgroup . In our most recent studies, the ONB-based synthetic lipids were investigated as novel drug delivery carriers for anticancer drugs. , The cell viability and hemolytic assays revealed that ONB-based lipids have a good safety profile.…”

Section: Introductionmentioning

confidence: 99%

Exploring the Physical Properties of Lipid Membranes with Polyhydroxy Oxanorbornane Head Group Using NBD-Conjugated and DPH Fluorescent Probes

Sahu,

Reddy,

Kannoth Manheri

et al. 2024

Langmuir

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The present study focuses on exploring the physical properties of lipid membranes based on the polyhydroxy oxanorbornane (PH-ONB) headgroup, designed as synthetic analogues of naturally occurring archaeal lipid membranes. Specifically, we study two variants of PH-ONB headgroup-based lipids differing in the number of hydroxy groups present in the headgroup, with one having two hydroxy groups (ONB-2OH) and the other having three (ONB-3OH). These lipids form stable bilayer membranes. The study begins with a comprehensive analysis of the fluorescence characteristics of nitrobenzoxadiazole (NBD)-tagged ONB-based lipids in different solvent environments and within a model lipid membrane 1,2-dimyristoyl-sn-glycero-3phosphocholine (DMPC). Subsequently, the physical properties of the ONB-based membranes were examined by using an NBDtagged ONB-based probe and a commonly used extrinsic 1,6-diphenyl-1,3,5-hexatriene (DPH) fluorescent probe. The steady-state and time-resolved fluorescence properties of the NBD-tagged ONB-based probe and DPH were used to compare the physical properties of the ONB-based membranes, including polarity, fluidity, phase transition, order, hydration, location, heterogeneity, and rotational diffusion. The solid gel to liquid crystalline phase transition temperatures of ONB-2OH and ONB-3OH lipid membranes are found to be (68 ± 1) °C and (74 ± 1) °C, respectively. The variation in organization (size), fluidity, and phase transition temperature of ONB-based lipid membranes is explained by the extent of hydrogen bonding interactions between lipid head groups. ONB-based membranes exhibit characteristics similar to those of phospholipid membranes and possess a notably high phase transition temperature. These properties make them a promising and cost-effective synthetic alternative to archaeal lipid membranes with a wide range of potential applications.

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Section: Introductionmentioning

confidence: 99%

Exploring the Physical Properties of Lipid Membranes with Polyhydroxy Oxanorbornane Head Group Using NBD-Conjugated and DPH Fluorescent Probes

Sahu,

Reddy,

Kannoth Manheri

et al. 2024

Langmuir

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Sequential Release of Ibuprofen and the Gasotransmitter Hydrogen sulfide using Oxanorbornane‐Based Synthetic Lipids as Carriers

Kana Veedu,

Panthalattu Parambil,

Manheri

2024

ChemPlusChem

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After understanding the biological signaling roles of hydrogen sulfide and its involvement in various physiological processes, there has been enormous interest in exploring its therapeutic utility in areas such as cancer, inflammation, cardiovascular diseases, etc. There is also growing interest in using suitable H2S donors in combination with other drugs to improve the treatment outcome through the modulation of multiple pathways. The premature release of H2S from small molecule donors and the difficulty in controlling its spatio‐temporal distribution are the major challenges during these efforts. Hence the development of appropriate carriers that can release this gasotransmitter along with the therapeutic entity of interest in a controlled manner has high significance. In this regard, this report presents a novel drug delivery system from oxanorbornane‐based synthetic lipids that carries a H2S‐releasing 1,2‐dithiole‐3‐thione moiety as part of the head group. Nanoaggregates of the resulting conjugate are not only capable of efficiently entrapping a non‐steroidal anti‐inflammatory drug such as ibuprofen, but also release this drug and H2S in a controlled and sequential manner.

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Cancer cell uptake and distribution of oxanorbornane-based synthetic lipids and their prospects as novel drug delivery systems

Kesavan

Reddy

Kurian

et al. 2022

Journal of Drug Delivery Science and Technology

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1‐Hydroxymethyl‐7‐oxabicyclo[2.2.1]hept‐2‐ene skeleton in enantiopure form through enzymatic kinetic resolution

Cited by 7 publications

References 84 publications

Exploring the Physical Properties of Lipid Membranes with Polyhydroxy Oxanorbornane Head Group Using NBD-Conjugated and DPH Fluorescent Probes

Exploring the Physical Properties of Lipid Membranes with Polyhydroxy Oxanorbornane Head Group Using NBD-Conjugated and DPH Fluorescent Probes

Sequential Release of Ibuprofen and the Gasotransmitter Hydrogen sulfide using Oxanorbornane‐Based Synthetic Lipids as Carriers

Cancer cell uptake and distribution of oxanorbornane-based synthetic lipids and their prospects as novel drug delivery systems

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