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Beyond the Dimer and Trimer: Tetraspiro[2.1.2(5).1.2(9).1.2(13).1(3)] hexadecane-1,3,5,7-tetraone--the Cyclic Tetramer of Carbonylcyclopropane.

Chemistry (Weinheim an der Bergstrasse, Germany)

Sedenkova KN, Averina EB, Grishin YK, Andriasov KS, Stepanova SA, Roznyatovsky VA, Kutateladze AG, Rybakov VB, Albov DV, Kuznetsova TS, Zefirov NS.
PMID: 26762227
Chemistry. 2016 Mar 14;22(12):3996-9. doi: 10.1002/chem.201600140. Epub 2016 Feb 03.

Tetraspiro[2.1.2(5).1.2(9).1.2(13).1(3)]hexadecane-1,3,5,7-tetraone 4, a unique tetraketone containing a cyclooctane core and four spiroannelated cyclopropane moieties, represents the previously unknown cyclotetramer of carbonylcyclopropane. For this purpose oxidation of the parent polyspirocyclic hydrocarbon was examined under various oxidative conditions, and the reactivity...

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Sedenkova KN, Averina EB, Grishin YK, et al. Beyond the Dimer and Trimer: Tetraspiro[2.1.2(5).1.2(9).1.2(13).1(3)] hexadecane-1,3,5,7-tetraone--the Cyclic Tetramer of Carbonylcyclopropane. Chemistry. 2016;22(12):3996-9doi: 10.1002/chem.201600140.
Sedenkova, K. N., Averina, E. B., Grishin, Y. K., Andriasov, K. S., Stepanova, S. A., Roznyatovsky, V. A., Kutateladze, A. G., Rybakov, V. B., Albov, D. V., Kuznetsova, T. S., & Zefirov, N. S. (2016). Beyond the Dimer and Trimer: Tetraspiro[2.1.2(5).1.2(9).1.2(13).1(3)] hexadecane-1,3,5,7-tetraone--the Cyclic Tetramer of Carbonylcyclopropane. Chemistry (Weinheim an der Bergstrasse, Germany), 22(12), 3996-9. https://doi.org/10.1002/chem.201600140
Sedenkova, Kseniya N, et al. "Beyond the Dimer and Trimer: Tetraspiro[2.1.2(5).1.2(9).1.2(13).1(3)] hexadecane-1,3,5,7-tetraone--the Cyclic Tetramer of Carbonylcyclopropane." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,12 (2016): 3996-9. doi: https://doi.org/10.1002/chem.201600140
Sedenkova KN, Averina EB, Grishin YK, Andriasov KS, Stepanova SA, Roznyatovsky VA, Kutateladze AG, Rybakov VB, Albov DV, Kuznetsova TS, Zefirov NS. Beyond the Dimer and Trimer: Tetraspiro[2.1.2(5).1.2(9).1.2(13).1(3)] hexadecane-1,3,5,7-tetraone--the Cyclic Tetramer of Carbonylcyclopropane. Chemistry. 2016 Mar 14;22(12):3996-9. doi: 10.1002/chem.201600140. Epub 2016 Feb 03. PMID: 26762227.
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Photoassisted Diversity-Oriented Synthesis: Intramolecular Cycloadditions of Photogenerated Azaxylylenes with Oxazole Pendants, and Subsequent Postphotochemical Multicomponent Modifications.

Organic letters

Kumar NN, Kutateladze AG.
PMID: 26760049
Org Lett. 2016 Feb 05;18(3):460-3. doi: 10.1021/acs.orglett.5b03503. Epub 2016 Jan 13.

Photogenerated aza-o-xylylenes undergo intramolecular cycloaddition reactions to tethered oxazoles, with primary photoproducts featuring a reactive cyclic imine moiety suitable for multicomponent postphotochemical transformations. For example, the reaction of these imine photoproducts with bromoacetyl bromide leads to a key 1,4-dielectrophilic...

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Kumar NN, Kutateladze AG. Photoassisted Diversity-Oriented Synthesis: Intramolecular Cycloadditions of Photogenerated Azaxylylenes with Oxazole Pendants, and Subsequent Postphotochemical Multicomponent Modifications. Org Lett. 2016;18(3):460-3doi: 10.1021/acs.orglett.5b03503.
Kumar, N. N., & Kutateladze, A. G. (2016). Photoassisted Diversity-Oriented Synthesis: Intramolecular Cycloadditions of Photogenerated Azaxylylenes with Oxazole Pendants, and Subsequent Postphotochemical Multicomponent Modifications. Organic letters, 18(3), 460-3. https://doi.org/10.1021/acs.orglett.5b03503
Kumar, N N Bhuvan, and Kutateladze, Andrei G. "Photoassisted Diversity-Oriented Synthesis: Intramolecular Cycloadditions of Photogenerated Azaxylylenes with Oxazole Pendants, and Subsequent Postphotochemical Multicomponent Modifications." Organic letters vol. 18,3 (2016): 460-3. doi: https://doi.org/10.1021/acs.orglett.5b03503
Kumar NN, Kutateladze AG. Photoassisted Diversity-Oriented Synthesis: Intramolecular Cycloadditions of Photogenerated Azaxylylenes with Oxazole Pendants, and Subsequent Postphotochemical Multicomponent Modifications. Org Lett. 2016 Feb 05;18(3):460-3. doi: 10.1021/acs.orglett.5b03503. Epub 2016 Jan 13. PMID: 26760049.
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Intramolecular cycloadditions of photogenerated azaxylylenes: an experimental and theoretical study.

The journal of physical chemistry. A

Mukhina OA, Cronk WC, Kumar NN, Sekhar MC, Samanta A, Kutateladze AG.
PMID: 24958234
J Phys Chem A. 2014 Nov 13;118(45):10487-96. doi: 10.1021/jp504281y. Epub 2014 Jun 24.

The mechanism of intramolecular cycloadditions of azaxylylenes photogenerated via excited-state intramolecular proton transfer (ESIPT) in aromatic o-amido ketones and aldehydes bearing unsaturated functionalities was studied experimentally and computationally. In time-correlated single-photon counting experiments, no relation was found between lifetimes...

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Mukhina OA, Cronk WC, Kumar NN, et al. Intramolecular cycloadditions of photogenerated azaxylylenes: an experimental and theoretical study. J Phys Chem A. 2014;118(45):10487-96doi: 10.1021/jp504281y.
Mukhina, O. A., Cronk, W. C., Kumar, N. N., Sekhar, M. C., Samanta, A., & Kutateladze, A. G. (2014). Intramolecular cycloadditions of photogenerated azaxylylenes: an experimental and theoretical study. The journal of physical chemistry. A, 118(45), 10487-96. https://doi.org/10.1021/jp504281y
Mukhina, Olga A, et al. "Intramolecular cycloadditions of photogenerated azaxylylenes: an experimental and theoretical study." The journal of physical chemistry. A vol. 118,45 (2014): 10487-96. doi: https://doi.org/10.1021/jp504281y
Mukhina OA, Cronk WC, Kumar NN, Sekhar MC, Samanta A, Kutateladze AG. Intramolecular cycloadditions of photogenerated azaxylylenes: an experimental and theoretical study. J Phys Chem A. 2014 Nov 13;118(45):10487-96. doi: 10.1021/jp504281y. Epub 2014 Jun 24. PMID: 24958234.
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New multiplex PCR methods for rapid screening of genetically modified organisms in foods.

Frontiers in microbiology

Datukishvili N, Kutateladze T, Gabriadze I, Bitskinashvili K, Vishnepolsky B.
PMID: 26257724
Front Microbiol. 2015 Jul 24;6:757. doi: 10.3389/fmicb.2015.00757. eCollection 2015.

We present novel multiplex PCR methods for rapid and reliable screening of genetically modified organisms (GMOs). New designed PCR primers targeting four frequently used GMO specific sequences permitted identification of new DNA markers, in particular 141 bp fragment of...

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Datukishvili N, Kutateladze T, Gabriadze I, et al. New multiplex PCR methods for rapid screening of genetically modified organisms in foods. Front Microbiol. 2015;6:757doi: 10.3389/fmicb.2015.00757.
Datukishvili, N., Kutateladze, T., Gabriadze, I., Bitskinashvili, K., & Vishnepolsky, B. (2015). New multiplex PCR methods for rapid screening of genetically modified organisms in foods. Frontiers in microbiology, 6757. https://doi.org/10.3389/fmicb.2015.00757
Datukishvili, Nelly, et al. "New multiplex PCR methods for rapid screening of genetically modified organisms in foods." Frontiers in microbiology vol. 6 (2015): 757. doi: https://doi.org/10.3389/fmicb.2015.00757
Datukishvili N, Kutateladze T, Gabriadze I, Bitskinashvili K, Vishnepolsky B. New multiplex PCR methods for rapid screening of genetically modified organisms in foods. Front Microbiol. 2015 Jul 24;6:757. doi: 10.3389/fmicb.2015.00757. eCollection 2015. PMID: 26257724; PMCID: PMC4513241.
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Photoinduced 1,3-proton shift in methyldithiepines as a potential way of modulating hyperpolarizabilities.

The Journal of organic chemistry

Wan Y, Kurchan A, Kutateladze A.
PMID: 11262142
J Org Chem. 2001 Mar 09;66(5):1894-9. doi: 10.1021/jo005707i.

No abstract available.

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Wan Y, Kurchan A, Kutateladze A. Photoinduced 1,3-proton shift in methyldithiepines as a potential way of modulating hyperpolarizabilities. J Org Chem. 2001;66(5):1894-9doi: 10.1021/jo005707i.
Wan, Y., Kurchan, A., & Kutateladze, A. (2001). Photoinduced 1,3-proton shift in methyldithiepines as a potential way of modulating hyperpolarizabilities. The Journal of organic chemistry, 66(5), 1894-9. https://doi.org/10.1021/jo005707i
Wan, Y, et al. "Photoinduced 1,3-proton shift in methyldithiepines as a potential way of modulating hyperpolarizabilities." The Journal of organic chemistry vol. 66,5 (2001): 1894-9. doi: https://doi.org/10.1021/jo005707i
Wan Y, Kurchan A, Kutateladze A. Photoinduced 1,3-proton shift in methyldithiepines as a potential way of modulating hyperpolarizabilities. J Org Chem. 2001 Mar 09;66(5):1894-9. doi: 10.1021/jo005707i. PMID: 11262142.
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Effect of beta-alkylthioethyl substitution in 1,3-dithianes: quasianchimeric assistance in photoinduced electron transfer?.

The Journal of organic chemistry

Valiulin RV, Kutateladze AG.
PMID: 18630878
J Org Chem. 2008 Aug 15;73(16):6393-6. doi: 10.1021/jo800938d. Epub 2008 Jul 16.

Nanosecond laser flash photolysis (LFP) experiments show that the rates of ET quenching of triplet benzophenone by 2-alkyldithianes significantly decrease with bulkier substitution. Introduction of sulfur at the beta-position of the flexible alkyl chain reverses this trend, whereas such...

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Valiulin RV, Kutateladze AG. Effect of beta-alkylthioethyl substitution in 1,3-dithianes: quasianchimeric assistance in photoinduced electron transfer?. J Org Chem. 2008;73(16):6393-6doi: 10.1021/jo800938d.
Valiulin, R. V., & Kutateladze, A. G. (2008). Effect of beta-alkylthioethyl substitution in 1,3-dithianes: quasianchimeric assistance in photoinduced electron transfer?. The Journal of organic chemistry, 73(16), 6393-6. https://doi.org/10.1021/jo800938d
Valiulin, Roman V, and Kutateladze, Andrei G. "Effect of beta-alkylthioethyl substitution in 1,3-dithianes: quasianchimeric assistance in photoinduced electron transfer?." The Journal of organic chemistry vol. 73,16 (2008): 6393-6. doi: https://doi.org/10.1021/jo800938d
Valiulin RV, Kutateladze AG. Effect of beta-alkylthioethyl substitution in 1,3-dithianes: quasianchimeric assistance in photoinduced electron transfer?. J Org Chem. 2008 Aug 15;73(16):6393-6. doi: 10.1021/jo800938d. Epub 2008 Jul 16. PMID: 18630878.
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Intramolecular photoassisted cycloadditions of azaxylylenes and postphotochemical capstone modifications via Suzuki coupling provide access to complex polyheterocyclic biaryls.

The Journal of organic chemistry

Cronk WC, Mukhina OA, Kutateladze AG.
PMID: 24397435
J Org Chem. 2014 Feb 07;79(3):1235-46. doi: 10.1021/jo4026447. Epub 2014 Jan 14.

Modular preassembly of azaxylylene photoprecursors, halogen-substituted in the aromatic ring, their intramolecular [4 + 4] or [4 + 2] cycloadditions to tethered unsaturated pendants, and subsequent postphotochemical capstone modification of the primary photoproducts via Suzuki coupling provides rapid access...

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Cronk WC, Mukhina OA, Kutateladze AG. Intramolecular photoassisted cycloadditions of azaxylylenes and postphotochemical capstone modifications via Suzuki coupling provide access to complex polyheterocyclic biaryls. J Org Chem. 2014;79(3):1235-46doi: 10.1021/jo4026447.
Cronk, W. C., Mukhina, O. A., & Kutateladze, A. G. (2014). Intramolecular photoassisted cycloadditions of azaxylylenes and postphotochemical capstone modifications via Suzuki coupling provide access to complex polyheterocyclic biaryls. The Journal of organic chemistry, 79(3), 1235-46. https://doi.org/10.1021/jo4026447
Cronk, W Cole, et al. "Intramolecular photoassisted cycloadditions of azaxylylenes and postphotochemical capstone modifications via Suzuki coupling provide access to complex polyheterocyclic biaryls." The Journal of organic chemistry vol. 79,3 (2014): 1235-46. doi: https://doi.org/10.1021/jo4026447
Cronk WC, Mukhina OA, Kutateladze AG. Intramolecular photoassisted cycloadditions of azaxylylenes and postphotochemical capstone modifications via Suzuki coupling provide access to complex polyheterocyclic biaryls. J Org Chem. 2014 Feb 07;79(3):1235-46. doi: 10.1021/jo4026447. Epub 2014 Jan 14. PMID: 24397435.
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A triple action CDK4/6-PI3K-BET inhibitor with augmented cancer cell cytotoxicity.

Cell discovery

Burgoyne AM, Vann KR, Joshi S, Morales GA, Vega FM, Singh A, Pal D, Merati AB, Kutateladze TG, Durden DL.
PMID: 34315865
Cell Discov. 2020 Jul 28;6(1):49. doi: 10.1038/s41421-020-0181-z.

No abstract available.

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Burgoyne AM, Vann KR, Joshi S, et al. A triple action CDK4/6-PI3K-BET inhibitor with augmented cancer cell cytotoxicity. Cell Discov. 2020;6(1):49doi: 10.1038/s41421-020-0181-z.
Burgoyne, A. M., Vann, K. R., Joshi, S., Morales, G. A., Vega, F. M., Singh, A., Pal, D., Merati, A. B., Kutateladze, T. G., & Durden, D. L. (2020). A triple action CDK4/6-PI3K-BET inhibitor with augmented cancer cell cytotoxicity. Cell discovery, 6(1), 49. https://doi.org/10.1038/s41421-020-0181-z
Burgoyne, Adam M, et al. "A triple action CDK4/6-PI3K-BET inhibitor with augmented cancer cell cytotoxicity." Cell discovery vol. 6,1 (2020): 49. doi: https://doi.org/10.1038/s41421-020-0181-z
Burgoyne AM, Vann KR, Joshi S, Morales GA, Vega FM, Singh A, Pal D, Merati AB, Kutateladze TG, Durden DL. A triple action CDK4/6-PI3K-BET inhibitor with augmented cancer cell cytotoxicity. Cell Discov. 2020 Jul 28;6(1):49. doi: 10.1038/s41421-020-0181-z. PMID: 34315865.
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The BTK/PI3K/BRD4 axis inhibitor SRX3262 overcomes Ibrutinib resistance in mantle cell lymphoma.

iScience

Pal D, Vann KR, Joshi S, Sahar NE, Morales GA, El-Gamal D, Kutateladze TG, Durden DL.
PMID: 34557659
iScience. 2021 Jul 30;24(9):102931. doi: 10.1016/j.isci.2021.102931. eCollection 2021 Sep 24.

Mantle cell lymphoma (MCL) is an aggressive subtype of non-Hodgkin's lymphoma and one of the most challenging blood cancers to combat due to frequent relapse after treatment. Here, we developed the first-in-class BTK/PI3K/BRD4 axis inhibitor SRX3262, which simultaneously blocks...

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Pal D, Vann KR, Joshi S, et al. The BTK/PI3K/BRD4 axis inhibitor SRX3262 overcomes Ibrutinib resistance in mantle cell lymphoma. iScience. 2021;24(9):102931doi: 10.1016/j.isci.2021.102931.
Pal, D., Vann, K. R., Joshi, S., Sahar, N. E., Morales, G. A., El-Gamal, D., Kutateladze, T. G., & Durden, D. L. (2021). The BTK/PI3K/BRD4 axis inhibitor SRX3262 overcomes Ibrutinib resistance in mantle cell lymphoma. iScience, 24(9), 102931. https://doi.org/10.1016/j.isci.2021.102931
Pal, Dhananjaya, et al. "The BTK/PI3K/BRD4 axis inhibitor SRX3262 overcomes Ibrutinib resistance in mantle cell lymphoma." iScience vol. 24,9 (2021): 102931. doi: https://doi.org/10.1016/j.isci.2021.102931
Pal D, Vann KR, Joshi S, Sahar NE, Morales GA, El-Gamal D, Kutateladze TG, Durden DL. The BTK/PI3K/BRD4 axis inhibitor SRX3262 overcomes Ibrutinib resistance in mantle cell lymphoma. iScience. 2021 Jul 30;24(9):102931. doi: 10.1016/j.isci.2021.102931. eCollection 2021 Sep 24. PMID: 34557659; PMCID: PMC8445847.
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Protocol for Biochemical Analysis and Structure Determination of the ZZ Domain of the E3 Ubiquitin Ligase HERC2.

STAR protocols

Liu J, Xue Z, Vann KR, Shi X, Kutateladze TG.
PMID: 33377049
STAR Protoc. 2020 Oct 28;1(3):100155. doi: 10.1016/j.xpro.2020.100155. eCollection 2020 Dec 18.

Since its discovery, several ligands of the ZZ domain have been identified; however, molecular and structural information underlying binding of these ligands remains limited. Here, we describe a protocol for biochemical and structural analysis of the ZZ domain of...

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Liu J, Xue Z, Vann KR, et al. Protocol for Biochemical Analysis and Structure Determination of the ZZ Domain of the E3 Ubiquitin Ligase HERC2. STAR Protoc. 2020;1(3):100155doi: 10.1016/j.xpro.2020.100155.
Liu, J., Xue, Z., Vann, K. R., Shi, X., & Kutateladze, T. G. (2020). Protocol for Biochemical Analysis and Structure Determination of the ZZ Domain of the E3 Ubiquitin Ligase HERC2. STAR protocols, 1(3), 100155. https://doi.org/10.1016/j.xpro.2020.100155
Liu, Jiuyang, et al. "Protocol for Biochemical Analysis and Structure Determination of the ZZ Domain of the E3 Ubiquitin Ligase HERC2." STAR protocols vol. 1,3 (2020): 100155. doi: https://doi.org/10.1016/j.xpro.2020.100155
Liu J, Xue Z, Vann KR, Shi X, Kutateladze TG. Protocol for Biochemical Analysis and Structure Determination of the ZZ Domain of the E3 Ubiquitin Ligase HERC2. STAR Protoc. 2020 Oct 28;1(3):100155. doi: 10.1016/j.xpro.2020.100155. eCollection 2020 Dec 18. PMID: 33377049; PMCID: PMC7757301.
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DU8+ Computations Reveal a Common Challenge in the Structure Assignment of Natural Products Containing a Carboxylic Anhydride Moiety.

The Journal of organic chemistry

Novitskiy IM, Kutateladze AG.
PMID: 34743508
J Org Chem. 2021 Dec 03;86(23):17511-17515. doi: 10.1021/acs.joc.1c02291. Epub 2021 Nov 08.

DU8+ computations of NMR spectra revealed a relatively common error in the structure assignment of carboxylic anhydride-containing natural products. Computationally driven revisions of ten of these structures are reported in this Note. The majority of the misassigned structures featured...

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Novitskiy IM, Kutateladze AG. DU8+ Computations Reveal a Common Challenge in the Structure Assignment of Natural Products Containing a Carboxylic Anhydride Moiety. J Org Chem. 2021;86(23):17511-17515doi: 10.1021/acs.joc.1c02291.
Novitskiy, I. M., & Kutateladze, A. G. (2021). DU8+ Computations Reveal a Common Challenge in the Structure Assignment of Natural Products Containing a Carboxylic Anhydride Moiety. The Journal of organic chemistry, 86(23), 17511-17515. https://doi.org/10.1021/acs.joc.1c02291
Novitskiy, Ivan M, and Kutateladze, Andrei G. "DU8+ Computations Reveal a Common Challenge in the Structure Assignment of Natural Products Containing a Carboxylic Anhydride Moiety." The Journal of organic chemistry vol. 86,23 (2021): 17511-17515. doi: https://doi.org/10.1021/acs.joc.1c02291
Novitskiy IM, Kutateladze AG. DU8+ Computations Reveal a Common Challenge in the Structure Assignment of Natural Products Containing a Carboxylic Anhydride Moiety. J Org Chem. 2021 Dec 03;86(23):17511-17515. doi: 10.1021/acs.joc.1c02291. Epub 2021 Nov 08. PMID: 34743508.
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Combinatorial inhibition of BTK, PI3K-AKT and BRD4-MYC as a strategy for treatment of mantle cell lymphoma.

Molecular biomedicine

Vann KR, Pal D, Smith AL, Sahar NE, Krishnaiah M, El-Gamal D, Kutateladze TG.
PMID: 35031886
Mol Biomed. 2022 Jan 15;3(1):2. doi: 10.1186/s43556-021-00066-9.

Mantle cell lymphoma (MCL) is a subtype of non-Hodgkin's lymphoma characterized by poor prognosis. The complexity of MCL pathogenesis arises from aberrant activities of diverse signaling pathways, including BTK, PI3K-AKT-mTOR and MYC-BRD4. Here, we report that MCL-related signaling pathways...

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Vann KR, Pal D, Smith AL, et al. Combinatorial inhibition of BTK, PI3K-AKT and BRD4-MYC as a strategy for treatment of mantle cell lymphoma. Mol Biomed. 2022;3(1):2doi: 10.1186/s43556-021-00066-9.
Vann, K. R., Pal, D., Smith, A. L., Sahar, N. E., Krishnaiah, M., El-Gamal, D., & Kutateladze, T. G. (2022). Combinatorial inhibition of BTK, PI3K-AKT and BRD4-MYC as a strategy for treatment of mantle cell lymphoma. Molecular biomedicine, 3(1), 2. https://doi.org/10.1186/s43556-021-00066-9
Vann, Kendra R, et al. "Combinatorial inhibition of BTK, PI3K-AKT and BRD4-MYC as a strategy for treatment of mantle cell lymphoma." Molecular biomedicine vol. 3,1 (2022): 2. doi: https://doi.org/10.1186/s43556-021-00066-9
Vann KR, Pal D, Smith AL, Sahar NE, Krishnaiah M, El-Gamal D, Kutateladze TG. Combinatorial inhibition of BTK, PI3K-AKT and BRD4-MYC as a strategy for treatment of mantle cell lymphoma. Mol Biomed. 2022 Jan 15;3(1):2. doi: 10.1186/s43556-021-00066-9. PMID: 35031886.
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