NDLI: Chromatographic Enantioresolution of Six Purine Derivatives Endowed with Anti-Human Breast Cancer Activity

Content Provider	Springer Nature Link
Author	Natalini, Benedetto Sardella, Roccaldo Ianni, Federica García Rubiño, María Eugenia Conejo García, Ana Núñez, María del Carmen Gallo, Miguel Angel Campos, Joaquín María
Copyright Year	2013
Abstract	Three (R,S)-9-(2,3-dihydro-1,4-benzoxathiin-3-ylmethyl)-9H-purine derivatives (1–3) and three (R,S)-9-(2,3-dihydro-1,4-benzoxathiin-2-ylmethyl)-9H-purine derivatives (4–6) showed relevant activity against human breast cancer cell line MCF-7, when assayed as racemates. The relevant structural analogy among these compounds stimulated us to evaluate and compare their chromatographic behaviour with five polysaccharide-based chiral stationary phases (CSPs). For a column screening purpose, four cellulose-based (Chiralcel OD-H, Chiralpak IB, Lux Cellulose-2, and Sepapak-4; CSPs 1–4, respectively) and an amylose-based (Lux Amylose-2; CSP 5) CSPs were initially assayed by employing the same “standard” eluent mixture. With CSP 2, the performance from “non standard” eluent systems was also evaluated. The different type and position of the substituents onto the carbamate moiety, the coated or immobilized nature of the modified polymer chain, and the different type of winding as well as the eluent composition were found to deeply affect the enantiorecognition mechanism. While the different winding of the polymer and the derived different morphology of the binding cleft in the 2,5-disubstituted chloromethyl phenyl carbamate amylose-based CSP 5 was found to be unsuited to get profitable enantio-discriminations of all the analyzed compounds, CSP 3 and CSP 4 produced the highest α and R S values in the enantioselective analysis of four out of six racemates (that is 1–3 and 6). In CSP 2, the conformational change of the polysaccharide chain upon immobilization produced a profound influence on the chromatographic behaviour of compounds 1–6. A relevant improvement of the enantioresolution quality of CSP 2 was obtained when used in combination with “non standard” solvents as constituents of the mobile phase mixture.
Starting Page	475
Ending Page	482
Page Count	8
File Format	PDF
ISSN	00095893
Journal	Chromatographia
Volume Number	76
Issue Number	9-10
e-ISSN	16121112
Language	English
Publisher	Springer-Verlag
Publisher Date	2013-01-30
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Liquid chromatography Polysaccharide-based chiral stationary phases Column screening Non-standard solvents Enantiomer resolution Chromatography Proteomics Pharmacy Laboratory Medicine
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Analytical Chemistry Biochemistry Clinical Biochemistry

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

Chiral Separation of 4-Iminoflavan Derivatives on Several Polysaccharide-Based Chiral Stationary Phases by HPLC

Small Molecules as Chromatographic Tools for HPLC Enantiomeric Resolution: Pirkle-Type Chiral Stationary Phases Evolution

HPLC Separation of Enantiomers of Some Chiral Carboxylic Acid Derivatives Using Polysaccharide-Based Chiral Columns and Polar Organic Mobile Phases

Chiral Resolution of Enantiomers of Homocamptothecin Derivatives, Antitumor Topoisomerase I Inhibitors, Using High Performance Liquid Chromatography on Polysaccharide-Based Chiral Stationary Phases

HPLC Separation of Enantiomers of Some Flavanone Derivatives Using Polysaccharide-Based Chiral Selectors Covalently Immobilized on Silica

Liquid Chromatographic Resolution of Racemic α-Hydroxycarboxylic Acids on Ligand Exchange Chiral Stationary Phases

Enantioseparation of Chiral Antimycotic Drugs by HPLC with Polysaccharide-Based Chiral Columns and Polar Organic Mobile Phases with Emphasis on Enantiomer Elution Order

Preparation of Regioselectively Modified Amylose Derivatives and Their Applications in Chiral HPLC

Separation of the enantiomers of amino acid esters as benzophenone imine derivatives on polysaccharide-derived chiral stationary phases

Chromatographic Enantioresolution of Six Purine Derivatives Endowed with Anti-Human Breast Cancer Activity

Similar Documents

Chiral Separation of 4-Iminoflavan Derivatives on Several Polysaccharide-Based Chiral Stationary Phases by HPLC

Small Molecules as Chromatographic Tools for HPLC Enantiomeric Resolution: Pirkle-Type Chiral Stationary Phases Evolution

HPLC Separation of Enantiomers of Some Chiral Carboxylic Acid Derivatives Using Polysaccharide-Based Chiral Columns and Polar Organic Mobile Phases

Chiral Resolution of Enantiomers of Homocamptothecin Derivatives, Antitumor Topoisomerase I Inhibitors, Using High Performance Liquid Chromatography on Polysaccharide-Based Chiral Stationary Phases

HPLC Separation of Enantiomers of Some Flavanone Derivatives Using Polysaccharide-Based Chiral Selectors Covalently Immobilized on Silica

Liquid Chromatographic Resolution of Racemic α-Hydroxycarboxylic Acids on Ligand Exchange Chiral Stationary Phases

Enantioseparation of Chiral Antimycotic Drugs by HPLC with Polysaccharide-Based Chiral Columns and Polar Organic Mobile Phases with Emphasis on Enantiomer Elution Order

Preparation of Regioselectively Modified Amylose Derivatives and Their Applications in Chiral HPLC

Separation of the enantiomers of amino acid esters as benzophenone imine derivatives on polysaccharide-derived chiral stationary phases

Chromatographic Enantioresolution of Six Purine Derivatives Endowed with Anti-Human Breast Cancer Activity