Structural Studies and Anticancer Activity of a Novel Class of β-Peptides
Functionalized oligomeric organic compounds with well‐defined β‐proline scaffold have been synthesized by a cycloadditive oligomerization approach in racemic and enantiopure forms. The structure of the novel β‐peptides was investigated by NMR spectroscopic and X‐ray methods determining the conformat...
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| Published in | Chemistry, an Asian journal Vol. 10; no. 2; pp. 383 - 389 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.02.2015
WILEY‐VCH Verlag |
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| Abstract | Functionalized oligomeric organic compounds with well‐defined β‐proline scaffold have been synthesized by a cycloadditive oligomerization approach in racemic and enantiopure forms. The structure of the novel β‐peptides was investigated by NMR spectroscopic and X‐ray methods determining the conformational shapes of the β‐proline oligomers in solution and solid states. The main structural elements subject to conformational switches are β‐peptide bonds between 5‐arylpyrrolidine‐2‐carboxylic acid units existing in Z/E configurations. The whole library of short β‐peptides and intermediate acrylamides has been tested on antiproliferative activity towards the hormone‐refractory prostate cancer cell line PC‐3 revealing several oligomeric compounds with low micromolar and submicromolar activities. Bromine‐substituted dimeric and trimeric acrylamides induced caspase‐dependent apoptosis of PC‐3 cells through cell‐cycle arrest and mitochondrial damage.
Oligomers stop proliferation: Cycloadditive oligomerization efficiently produces a set of well‐defined β‐peptides having potent activity for the reduction of growth of prostate cancer cells. |
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| AbstractList | Functionalized oligomeric organic compounds with well-defined β-proline scaffold have been synthesized by a cycloadditive oligomerization approach in racemic and enantiopure forms. The structure of the novel β-peptides was investigated by NMR spectroscopic and X-ray methods determining the conformational shapes of the β-proline oligomers in solution and solid states. The main structural elements subject to conformational switches are β-peptide bonds between 5-arylpyrrolidine-2-carboxylic acid units existing in Z/E configurations. The whole library of short β-peptides and intermediate acrylamides has been tested on antiproliferative activity towards the hormone-refractory prostate cancer cell line PC-3 revealing several oligomeric compounds with low micromolar and submicromolar activities. Bromine-substituted dimeric and trimeric acrylamides induced caspase-dependent apoptosis of PC-3 cells through cell-cycle arrest and mitochondrial damage. Functionalized oligomeric organic compounds with well‐defined β‐proline scaffold have been synthesized by a cycloadditive oligomerization approach in racemic and enantiopure forms. The structure of the novel β‐peptides was investigated by NMR spectroscopic and X‐ray methods determining the conformational shapes of the β‐proline oligomers in solution and solid states. The main structural elements subject to conformational switches are β‐peptide bonds between 5‐arylpyrrolidine‐2‐carboxylic acid units existing in Z / E configurations. The whole library of short β‐peptides and intermediate acrylamides has been tested on antiproliferative activity towards the hormone‐refractory prostate cancer cell line PC‐3 revealing several oligomeric compounds with low micromolar and submicromolar activities. Bromine‐substituted dimeric and trimeric acrylamides induced caspase‐dependent apoptosis of PC‐3 cells through cell‐cycle arrest and mitochondrial damage. Functionalized oligomeric organic compounds with well‐defined β‐proline scaffold have been synthesized by a cycloadditive oligomerization approach in racemic and enantiopure forms. The structure of the novel β‐peptides was investigated by NMR spectroscopic and X‐ray methods determining the conformational shapes of the β‐proline oligomers in solution and solid states. The main structural elements subject to conformational switches are β‐peptide bonds between 5‐arylpyrrolidine‐2‐carboxylic acid units existing in Z/E configurations. The whole library of short β‐peptides and intermediate acrylamides has been tested on antiproliferative activity towards the hormone‐refractory prostate cancer cell line PC‐3 revealing several oligomeric compounds with low micromolar and submicromolar activities. Bromine‐substituted dimeric and trimeric acrylamides induced caspase‐dependent apoptosis of PC‐3 cells through cell‐cycle arrest and mitochondrial damage. Oligomers stop proliferation: Cycloadditive oligomerization efficiently produces a set of well‐defined β‐peptides having potent activity for the reduction of growth of prostate cancer cells. Functionalized oligomeric organic compounds with well-defined β-proline scaffold have been synthesized by a cycloadditive oligomerization approach in racemic and enantiopure forms. The structure of the novel β-peptides was investigated by NMR spectroscopic and X-ray methods determining the conformational shapes of the β-proline oligomers in solution and solid states. The main structural elements subject to conformational switches are β-peptide bonds between 5-arylpyrrolidine-2-carboxylic acid units existing in Z/E configurations. The whole library of short β-peptides and intermediate acrylamides has been tested on antiproliferative activity towards the hormone-refractory prostate cancer cell line PC-3 revealing several oligomeric compounds with low micromolar and submicromolar activities. Bromine-substituted dimeric and trimeric acrylamides induced caspase-dependent apoptosis of PC-3 cells through cell-cycle arrest and mitochondrial damage.Functionalized oligomeric organic compounds with well-defined β-proline scaffold have been synthesized by a cycloadditive oligomerization approach in racemic and enantiopure forms. The structure of the novel β-peptides was investigated by NMR spectroscopic and X-ray methods determining the conformational shapes of the β-proline oligomers in solution and solid states. The main structural elements subject to conformational switches are β-peptide bonds between 5-arylpyrrolidine-2-carboxylic acid units existing in Z/E configurations. The whole library of short β-peptides and intermediate acrylamides has been tested on antiproliferative activity towards the hormone-refractory prostate cancer cell line PC-3 revealing several oligomeric compounds with low micromolar and submicromolar activities. Bromine-substituted dimeric and trimeric acrylamides induced caspase-dependent apoptosis of PC-3 cells through cell-cycle arrest and mitochondrial damage. |
| Author | Yu, Chia-Chun Ivantcova, Polina M. Churakov, Andrei V. Zefirov, Nikolay S. Guh, Jih-Hwa Polshakov, Vladimir I. Kudryavtsev, Konstantin V. Bräse, Stefan |
| Author_xml | – sequence: 1 givenname: Konstantin V. surname: Kudryavtsev fullname: Kudryavtsev, Konstantin V. email: kudr@med.chem.msu.ru organization: Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow (Russian Federation) – sequence: 2 givenname: Chia-Chun surname: Yu fullname: Yu, Chia-Chun organization: School of Pharmacy, National Taiwan University, No.1, Sect. 1, Jen-Ai Rd, Taipei 100 (Taiwan) – sequence: 3 givenname: Polina M. surname: Ivantcova fullname: Ivantcova, Polina M. organization: Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow (Russian Federation) – sequence: 4 givenname: Vladimir I. surname: Polshakov fullname: Polshakov, Vladimir I. organization: Faculty of Fundamental Medicine, M. V. Lomonosov Moscow State University, 119991 Moscow (Russian Federation) – sequence: 5 givenname: Andrei V. surname: Churakov fullname: Churakov, Andrei V. organization: Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii prosp. 31, 119991 Moscow (Russian Federation) – sequence: 6 givenname: Stefan surname: Bräse fullname: Bräse, Stefan organization: Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76133 Karlsruhe (Germany) – sequence: 7 givenname: Nikolay S. surname: Zefirov fullname: Zefirov, Nikolay S. organization: Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow (Russian Federation) – sequence: 8 givenname: Jih-Hwa surname: Guh fullname: Guh, Jih-Hwa email: jhguh@ntu.edu.tw organization: School of Pharmacy, National Taiwan University, No.1, Sect. 1, Jen-Ai Rd, Taipei 100 (Taiwan) |
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| Copyright | 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
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| Keywords | mTOR pathway prostate cancer cycloaddition antiproliferative agents oligomers β-proline |
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| Snippet | Functionalized oligomeric organic compounds with well‐defined β‐proline scaffold have been synthesized by a cycloadditive oligomerization approach in racemic... Functionalized oligomeric organic compounds with well-defined β-proline scaffold have been synthesized by a cycloadditive oligomerization approach in racemic... |
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| SubjectTerms | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - toxicity antiproliferative agents Apoptosis - drug effects Caspases - metabolism Cell Cycle Checkpoints - drug effects Cell Line, Tumor cycloaddition Cycloaddition Reaction Humans Membrane Potential, Mitochondrial - drug effects mTOR pathway oligomers Peptides - chemical synthesis Peptides - chemistry Peptides - toxicity Proline - analogs & derivatives Proline - chemistry prostate cancer Protein Conformation Stereoisomerism β-proline |
| Title | Structural Studies and Anticancer Activity of a Novel Class of β-Peptides |
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