New Approaches Towards Synthesis of Enigmol Sphingolipids and its Analogues as Anti- Cancer agents.

PI Details Co-PI Details
Dr. Vasundhara Singh

Designation: Professor
Department: Applied Sciences
Email ID: Vasun7@gmail.co

 Dr. Navneet Agnihotri

Designation: Professor
Department: Department of Biochemistry, Panjab University
Email ID: Agnihotri.navneet@gmail.com
Funding Agency Project Cost
Department of Science and Technology-Science and Engineering Research Board (DST-SERB)

Rs. 27,75,520
Start Date Completion Date Status
2017-07-05 2021-07-04 Completed
Abstract
  1. Enigmol, a known anti-cancer 1-deoxyshingolipid and its stereo isomers have been synthesized by a new route starting from the chiral pool using both isomers of L-alanine via Stereoselective Grignard reaction and Cross metathesis reaction as the key steps.
  2. The Enigmol analogues have been synthesized by varying chain lengths and an additional additional hydroxyl group on the C-4 position of Enigmol and its chain analogues. The key reaction involved the installation of different lipophilic chain lengths via stereoselective cross metathesis reaction followed by mCPBA epoxidation, Red-Al ring opening and deprotection for the chain analogues and OsO4/NMO mediated dihydroxylation for the 4-hydroxy substituted analogues on the earlier synthesized 1-deoxysphingosines.
  3. The butyrate ceramides of the 1-deoxysphingosines have been synthesized using the oleic acid and butyric acid, a known chemo-preventative agents via N-Acylation using p-nitrophenyl oleate and butyrate respectively.
  4. A library of peptidomimetic 1-deoxysphingosine ceramides by Multi Component UGI Reaction have been synthesized using different aldehydes, cyclohexyl isocyanide and butyric acid with the previously synthesized 1- deoxysphingosine
  5. The in-vitro biological evaluation has been done on the PC-3 and HCT-116 cell lines and the IC50 value have been calculated giving the encouraging results
Manpower Sanctioned/Hired Manpower Trained

JRF- One (1)

Ph.D Produced- One (1)
Equipment Sanctioned/Procured
Publications
List of SCI Publications under Project

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DOI
Parleen Kaur, Vasundhara Singh* Synthesis and In Vitro Analysis of 1- Deoxysphingolipid Ceramide Analogues via UGI Reaction as Potential Anti- cancer Agents. Chemistry Select 7(2)   2022 10.1002/slct.202104 062.
Parleen Kaur, Vasundhara Singh* Comprehensive Insight view on Synthetic strategies of Enigmol and its analogues as Therapeutic agents. Mini- Reviews in Organic Chemistry 20 675-686 2023 10.2174/1570193X1 9666220820115630
 Parleen Kaur, Vasundhara Singh* 4-Hydroxy Enigmol, a 1- Deoxyphytosphingo lipid that Exhibit Good Activity against Prostate and Colon Cancer Chemistry Select 8(5)   2023 https://doi.org/10.10 02/slct.202203861
Output/Outcome of the Project