2023

Gupta, S.; Sharma, S. N.; Kundu, J.; Pattanayak, S.; and Sinha, S. Morpholino oligonucleotide-mediated exon skipping for DMD treatment: Past insights, present challenges and future perspectives. J. BioSci. 2023, 48:38 https://doi.org/10.1007/s12038-023-00365-z

 

Das, A.; Ghosh, A.; Kundu, J.; Egli, M.; Manoharan, M. and Sinha, S. Synthesis and Biophysical Studies of High-Affinity Morpholino Oligomers Containing G-clamp Analogs. J. Org. Chem. 2023, 88, 21, 15168–15175, https://doi.org/10.1021/acs.joc.3c01658

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Sarkar, S.; Kar, A.; Shaw, P.; DasGupta, B.; Keithellakpam, O. J.; Mukherjee, P. K.; Bhardwaj, P. K.; Sharma, N.; Haldar, P. K. and Sinha. S. Hydroalcoholic root extracts of Houttuynia cordata (Thunb.) standardized by UPLC-Q-TOF-MS/MS promotes apoptosis in human hepatocarcinoma cell HepG2 via GSK-3β/β-catenin/PDL-1 axis. Fitoterapia 2023,171,105684 (https://doi.org/10.1016/j.fitote.2023.105684)

 

Self-transfecting GMO-PMO antisense chimera targeting Nanog enable gene silencing in vitro and suppresses tumor growth in 4T1 allografts in mouse. Das, Ujjal.; Kundu, J.; Shaw, P.; Bose, C.; Ghosh, A.; Gupta, S.; Sarkar, S.; Bhadra, J.; and Sinha, S. Mol. Ther. Nucleic Acids 2023. https://doi.org/10.1016/j.omtn.2023.03.011

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Synthesis and Biophysical Properties of Phosphorodiamidate Piperidino Oligomers (PPOs). Ghosh, A.; Akabane-Nakata, M.; Kundu, J.; Harp, J. M.; Madaoui, M.; Egli, M.; Manoharan, M.;  and Sinha, S.

Org. Lett. 2023, 25, 6, 901–906, https://doi.org/10.1021/acs.orglett.2c04067

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Synthesis of Chlorophosphoramidate Monomer Morpholinos and PMOs. Kundu, J.; Ghosh, U.; Ghosh, A.; Pattanayak, S.; Das, A. and Sinha, S.  Current Protocols in Nucl. Acid Chem,  2023,3, 1-25, https://doi.org/10.1002/cpz1.686

 

C5-Pyrimidine-Functionalized Morpholino Oligonucleotides Exhibit Differential Binding Affinity, Target Specificity and Lipophilicity. Das, A.; Ghosh, A.; Sinha, S. Org. Biomol. Chem. 2023, 21, 1242 - 1253 https://doi.org/10.1039/D2OB01759H

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Synthesis of 5ʹ-Thiol Functionalized Morpholino Oligo-nucleotide and Subsequent Conjugation with IGT to Improve Delivery and Antisense Efficacy In Vitro. Ghosh, U.; Gupta, S. and Sinha, S. Bioconjugate Chem. 2023, 34, 174–180, https://doi.org/10.1021/acs.bioconjchem.2c00587

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2022

IGT mediated Nanog siRNA delivery in prostate cancer cells improves chemosensitization of Epirubicin in vitro.

Gupta, S.; Das, U.; Sinha, S. Bioorg. Med. Chem. Lett. 2022, https://doi.org/10.1016/j.bmcl.2022.129017.

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AUF-1 knock down in mice overarches butyrate driven hypo-cholesteraemia by conjuring 1 AUF-1-Dicer-1-miR122 hierarchy

Das, O.; Kundu, J.; Ghosh, A.; Gautam, A.; Ghosh, S.; Chakraborty, M.; Masid, A.; Gauri, S. S.; Mitra, D.; Dutta, M.; Mukherjee, B.; Sinha, S.; Bhaumik, M. BioRxiv 2022, https://doi.org/10.1101/2022.06.13.496022, Published in Frontiers Cellular and Infection Microbiology 2022, 1-20 (doi: 10.3389/fcimb.2022.1011386).

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Guanidinium Functionalized Flexible Azaproline Transporter for Efficient Intracellular Delivery of Proapoptotic Peptide and PDL1 Antisense Morpholino Oligo in Human Carcinoma Cells In Vitro.

Gupta, A.; Gupta, S.; Das, U. and Sinha, S. Bioconjugate Chem. 2022, 33, 907-917 https://doi.org/10.1021/acs.bioconjchem.2c00129

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J. Kundu, A. Ghosh, U. Ghosh, A. Das, D. Nagar, S. Pattanayak, A. Ghose and S. Sinha: Synthesis of Phosphorodiamidate Morpholino Oligonucleotides Using Trityl and Fmoc Chemistry in an Automated Oligo Synthesizer. J. Org. Chem. 2022, 87, 15, 9466–9478 https://doi.org/10.1021/acs.joc.2c00265

 

Mana, T.; Kundu, J.; Lahiri, H.; Bera, S.; Kolay, J.; Sinha, S.; Mukhopadhyay, R. Molecularly Resolved, Label-free Nucleic Acid Sensing at Solid-liquid Interface using Non-ionic DNA Analogues. RSC Adv. 2022, 12, 9263-9274, https://doi.org/10.1039/D2RA00386D

 

Bose, C.; Das, U.; Kuilya, T. K.; Mondal, J.; Bhadra, J.; Banerjee, P.; Goswami, R. K. and Sinha, S. Cananginone Abrogates EMT in Breast Cancer Cells through Hedgehog Signaling. Chem. Biodiversity 2022, e202100823 (https://doi.org/10.1002/cbdv.202100823)

 

Gupta, S.; Qasim, Md.; Gupta, A.; Kundu, J.; Sinha, S. Structural Modifications to the Internal Oligoguanidinium Transporter Uncover Two Potent Analogues that Effectively Deliver the Pro-apoptotic Peptide in Multiple Cancer Cell Lines. Bioconj. Chem. 2022, 33 (1), 121-133, doi.org/10.1021/acs.bioconjchem.1c00456

 

 

2021

Kundu, J.; Das, U.; Bose, C.; Bhadra, J. and Sinha, S. Self-transfecting GMO-PMO and PMO-GMO chimeras enable gene silencing in vitro and in vivo zebrafish model and NANOG Inhibition Induce the Apoptosis in Breast and Prostate Cancer Cells. BioRxiv 2021, https://doi.org/10.1101/2021.06.04.447039

 

Banerjee, I. ; Ghosh, K. C. ; Oheix, E. ; Jean, M.; Naubron, J-V.; Réglier, M.; Iranzo, O.* and Sinha, S.* Synthesis of Protected 3,4- and 2,3-Dimercaptophenylalanines as Building Blocks for Fmoc-Peptide Synthesis and Incorporation of the 3,4-Analogue in a Decapeptide Using Solid-Phase Synthesis. J. Org. Chem. 2021, 86, 2210−2223, doi.org/10.1021/acs.joc.0c02359.

 

2020

Chandra Bose, Priyanjalee Banerjee, Jayanta Kundu, Biswadeb Dutta, Indranil Ghosh, Shreya Sinha, Argha Ghosh, Abhishek Barua, Shalini Gupta, Ujjal Das, Siddhartha S. Jana, Surajit Sinha. Evaluation of tubulin targeted pyrimidine indole hybrid molecule as an anticancer agent. ChemSelect 2020, 5, 14021‒14031.

 

J. Kundu, P. Banerjee, C. Bose, U. Das, U. Ghosh and S. Sinha: Internal Oligoguanidinium Transporter: Mercury Free Scalable Synthesis, Improvement of Cellular Localization, Endosomal Escape, Mitochondrial Localization and Conjugation with Antisense Morpholino for NANOG Inhibition to Induce Chemosensitisation of Taxol in MCF-7 Cells. Bioconj. Chem. 2020, 31 (10), 2367‒2382, doi.org/10.1021/acs.bioconjchem.0c00444.

 

J. Kundu, U. Ghosh, A. Ghosh, A. Das, D. Nagar, A. Ghose and S. Sinha: Synthesis of Phosphorodiamidate Morpholino Oligonucleotides Using Trityl and Fmoc Chemistry-A New Method Amenable to Automated Synthesizer. ChemRxiv 2020, 10.26434/chemrxiv.12765563

 

2018-2019

Ghosh, K. C.; Duttagupta, I.; Bose, C.; Banerjee, P.; Gayen, A. K. and Sinha, S. Synthesis and anti-cancer activities of prolein-containing cyclic peptides and their linear analogs and congeners Syn. Commun. 2019, 49, 221‒236.

 

Ghosh K. C.; Banerjee, I. And Sinha, S. Montrillonite K 10 catalysed highly regioselective azidolysis of epoxides. A short and efficinat synthesis of phenylglycine. Syn. Commun. 2018, 48, 2923‒2934.

 

Khatra, H.; Khan, P. P.; Pattanayak, S.; Bhadra, J.; Rather, B.; Chakrabarti, S.; Saha, T. and Sinha, S. Hedgehog antagonist pyrimidine-indole-hybrid molecule inhibits ciliogenesis through microtubule destabilization. ChemBioChem 2018, 19, 723–735.

 

2010-2017

Nandi, B.; Khatra, H.; Khan, P. P.; Bhadra, J.; Pattanayak, S. and Sinha, S. “Cationic Cytosine Morpholino-Based Transporters: Synthesis and Regulation of Intracellular Localization”. ChemSelect 2017, 2, 5059–5067.

 

Khatra, H.; Bose, C. and Sinha, S. "Discovery of hedgehog antagonists for cancer therapy". Current Med. Chem. 2017, 24, 1–26, invited review).

 

Bhadra, J.; Pattanayak, S.; Khan, P. P.; Kundu, J.; Sinha, S. “Internal Oligoguanidinium-based Cellular Transporter Enhances Antisense Efficacy of Morpholinos in in vitro and Zebrafish model”. Bioconjugate Chem. 2016, 27, 2254–2259.

 

Khatra, H.; Kundu, J.; Khan, P. P.; Duttagupta, I.; Pattanayak, S. and Sinha, S. “Piperazic Acid Derivatives Inhibit Gli1 in Hedgehog Signaling Pathway”. Bioorg. Med. Chem. Lett. 2016, 26, 4423–4426.

 

Duttagupta, I.; Bhadra, J.; Das, S. K.; Sinha, S. “Proteolytic stability of α-hydrazino acid-containing peptides: a qualitative study”. Tetrahedron Lett. 2016, 57, 3858–3861.

 

Duttagupta, I.; Ghosh, K. C.; Sinha, S. “Synthetic Studies Toward Nonribosomal Peptides”. Studies in Natural Product Chem. (Elsevier, UK) (Elsevier, UK) 2016, 48, 31–66 (invited).

 

Duttagupta, I.; Misra, D.; Bhunya, S.; Paul, A.; Sinha, S. “Cis - Trans Conformational Analysis of δ – Azaproline in Peptides”. J. Org. Chem. 2015, 80, 10585−10604.

 

Bhadra, J.; Pattanayak, S. “Synthesis of Morpholino Monomers, Chlorophosphoramidate Monomers and Solid Phase Synthesis of Short Morpholino Oligomers”. Current Protocols in Nucl. Acid Chem. 2015, 4.65.1–4.65.26 (Wiley).

 

Bhadra, J.; Kundu, J.; Ghosh, K.; Sinha, S. “Synthesis of phosphorodiamidate morpholino oligonucleotides by H-phosphonate method”. Tetrahedron Lett. 2015, 56, 4565–4568.

 

Banerjee, T. S.; Paul, S.; Sinha, S.*; Das, S.* “Synthesis of iboga-like isoquinuclidines: Dual opioid receptors agonists having antinociceptive properties”. Bioorg. Med. Chem. 2014, 22, 6062–6070.

 

Chakraborty, A.; Jyothi, K.; Sinha, S. “Palladium-catalyzed synthesis of 2-allylindole and 2-allylbenzofuran derivatives from 2-((trimethylsilyl)ethynyl)arenes.” Tetrahedron Lett. 2014, 55, 6795–6798.

 

Duttagupta, I.; Goswami, K.; Chatla, P. and Sinha, S. “Improved Synthesis of Cyclic α-Hydrazino Acids of 5 to 9-Membered Rings and Optical Resolution of 5, 6, 7-Membered Ring Hydrazino Acids” Syn.Commun. 2014, 44, 2510–2519.

 

Paul, S.; Pattanayak, S.; Sinha, S. “Synthesis and Cell Transfection Properties of cationic uracil-morpholinotetramer”. Tetrahedron Lett. 2014, 55, 1072–1076.

 

Pattanayak, S.; Khatra, H.; Saha, S. and Sinha, S. “Cationic Morpholino Antisense Oligomer Conjugate: Synthesis, Cellular uptake and Inhibition of Gli1 in Hedgehog Hedgehog Signalling Pathway” RSC Advances 2014, 4, 1951–1954.

 

Paul, S.; Jana, S.; Bhadra, J.; Sinha, S. “Photophysical Studies and Submicron Ring Formation of Morpholino U-Nucleoside Monomers” Chem. Commun. 2013, 49, 11278–11280.

 

Chakraborty, A.; Goswami, K.; Adiyala, A.; Sinha, S. “Syntheses of Spiro[cyclopent[3]ene-1,3_-indole]s and Tetrahydrocyclo-hepta[b]indoles from 2,3-Disubstituted Indoles through Sigmatropic Rearrangement” Euro. J. Org. Chem. 2013, 7117–7127.

 

Goswami, K.; Chakraborty, A.; Sinha, S. “Synthesis of Optically Active Selenium-Containing Isotryptophan, Homoisotryptophan and Homotryptophan” Euro. J. Org. Chem. 2013, 3645–3647.

 

Nandi, B.; Pattanayak, S.; Paul, S. and Sinha, S. “Synthesis of Nucleobase-Functionalized Morpholino Modified Nucleoside Monomers Through Palladium-Catalyzed Cross-Coupling Reactions” Euro. J. Org. Chem. 2013, 1271–1286.

 

Pattanayak, S.; Paul, S.; Nandi, B. and Sinha, S. “Improved protocol for the synthesis of Flexibly ProtectedMorpholino Monomers from Unprotected Ribonucleosides” Nucleosides, Nucleotides and Nucleic Acids 2012, 31, 763–782.

 

Pattanayak, S.; Sinha, S. “Lithium bromide–DBU mediated synthesis of chlorophosphoramidate-activatedmorpholino nucleoside subunits” Tetrahedron Lett. 2012, 53, 6714–6717.

 

Duttagupta, I.; Goswami, K.; Sinha, S. “Synthesis of cyclic α-hydrazino acids” Tetrahedron 2012, 68,8347–8357.

 

Jana, G. K. and Sinha, S. “Total synthesis of ibogaine, epiibogaine and their analogues” Tetrahedron 2012,68, 7155–7165.

 

Paul, S.; Nandi, B.; Pattanayak, S.; Sinha, S. “Synthesis of 5-alkynylated uracil–morpholino monomersusing Sonogashira coupling” Tetrahedron Lett. 2012, 53, 4179–4183.

 

Jana, G. K. and Sinha, S. “Reductive Heck coupling: an efficient approach toward the iboga alkaloids.Synthesis of ibogamine, epiibogamine and iboga analogs” Tetrahedron Lett. 2012, 53, 1671-1674.

 

Goswami, K.; Duttagupta, I.; Sinha, S. “Synthesis of optically active homotryptophan and its oxygen andand sulfur analogues” Tetrahedron 2012, 68, 280–286.

 

Goswami, K.; Duttagupta, I.; Sinha, S. “Synthesis of Optically Active 2- and 3-Indolylglycine derivatives and their Oxygen Analogues” J. Org. Chem. 2012, 77, 7081−7085.

 

Pattanayak, S.; Sinha, S. “Ceric ammonium nitrate-mediated detritylation of tritylated amines” TetrahedronLett. 2011, 52, 34–37.

 

Paul, S.; Pattanayak, S.; Sinha, S. “Synthesis of new series of iboga analogues” Tetrahedron Lett. 2011,52, 6166–6169.

 

Chakraborty, A.; Sinha, S. “Synthesis of 3-[2-(1,3-butadienyl)]-1H-indoles en route to murrapanineanalogue” Tetrahedron Lett. 2011, 52, 6635–6638.

 

Jana, G. K.; Paul, S.; Sinha, S. “Recent Progress in the Synthesis of Iboga-alkaloids and their congeners”Org. Prep. Proc. International (Invited Review) 2011, 43, 541–573.

 

Nandi, B.; Sinha, S. “Alkylation of acylmetalates with alkyl halides to prepare Fischer carbine complexes:an improved protocol” Tetrahedron 2011, 67, 106–113.

 

Jana, G. K.; Sinha, S. “Synthesis of iboga alkaloids by Pd-catalyzed heteroannulation of 2-iodoaniline with an internal alkyne as the key step” Tetrahedron Lett. 2010, 51,1441–1443.

 

Jana, G. K.; Sinha, S. “A concise route to iboga-analogues via the formation of suitably substituted-2-indoles” Tetrahedron Lett. 2010, 51, 1994–1996.

 

 

Hyman, J. M.; Firestone, A. J.; Heine, V. M.; Zhao, Y.; Ocasio, C. A.; Han, K.; Sun, M.; Rack, P. G.; Surajit Sinha; Wu, J. J.; Solow-Cordero, D. E.; Jiang, J.; Rowitch, D. H.; James K. Chen. “Small-molecule inhibitors reveal multiple Strategies for Hedgehog pathway blockade” Proc. Natl. Acad. Sci USA 2009, 106,14132 – 14137.

 

Ouyang, X.; Shestopalov, I. A.; Surajit Sinha, Zheng, G.; Pitt, C. L. W.; Li, W. H.; Olson, A. J.; James K. Chen. “Versatile Synthesis and Rational Design of Caged Morpholinos” J. Am. Chem. Soc. 2009, 131, 13255–13269.

 

Cupido, T.; Rack, P. G.; Firestone, A. J.; Hyman, J. M.; Han, K.; Surajit Sinha; Ocasio, C. A. and James K. Chen. “The Imidazopyridine Derivative JK184 Reveals Dual Roles for Microtubules in Hedgehog Signaling.” Angew. Chem. Int. Ed. 2009, 48, 2321 – 2324.

 

Shestopalov, I. A.; Sinha, S.; Chen, J. K. “Light-controlled gene silencing in zebrafish embryos”. Nature Chemical Biology. 2007, 3, 650 - 651. (Authors contributed equally). (It was cited by the Faculty of 1000 as a "must read" with an F1000 factor of 6.4 and won ‘2008 NIH Pioneer Awards’).

 

Sinha, S.; Chen, J. K. “Purmorphamine activates the hedgehog pathway by targeting smoothened”. Nature Chemical Biology. 2006, 2, 29 – 30. (Work appeared as news and views in this issue).

 

Switzer, C.; Sinha S.; Kim, P. H.; Heuberger, B. D. “A purine-like Nickel (II) base-pair for DNA”. Angew. Chem. Int. Ed. 2005, 44, 1529 – 1532. (Hot off the Press, Mol. BioSyst. 2005, 1, 109-111).

 

Sinha S.; Kim, P. H.; Switzer, C. “2’-5’-linked DNA is a template for polymerase-directed DNA synthesis J. Am. Chem. Soc. 2004, 126, 40-41.

 

Post doctoral work: Chaput, J. C.; Sinha, S.; Switzer, C. “5-Propynyluracil diaminopurine: an efficient base-pair for non-enzymatic transcription of DNA”. Chem. Commun. 2002, 1568-1569.

 

Sinha, S.; Tilve, S.; Chandrasekaran, S. “A convenient synthesis of trans-3-hydroxy-L-proline” ARKIVOC (Gainesville, FL, United States). 2005, 11, 209-217.

 

Bhat, R. G.; Sinha, S.; Chandrasekaran, S. “Propargyloxycarbonyl (Poc) amino acid chlorides asefficient coupling reagents for the synthesis of 100% diastereopure peptides and resin boundtetrathiomolybdate as an effective deblocking agent for the Poc group”. Chem. Commun. 2002, 812-813.

 

Sridhar, P. R.; Sinha, S.; Chandrasekaran, S. “Highly selective deprotection of tert-butyl estersusing ytterbium triflate as a catalyst under mild conditions”. Indian Journal of Chemistry, SectionB, 2002, 41B(1), 157-160.

 

Sinha, S.; Mandal, B.; Chandrasekaran, S. “Insertion of ethyl acetate to aromatic compounds by meansof Friedel-Crafts reaction with -chloro--(ethylthio)-acetate catalyzed by ytterbium triflate.” Tetrahedron Lett. 2000, 41, 9109-9112.

 

Sinha, S.; Mandal, B.; Chandrasekaran, S. “Selective para metalation of 3-methoxy and 3,5-dimethoxy benzoic acids with LIC-KOR: synthesis of 3,5-dimethoxy-4-methyl benzoic acid”. Tetrahedron Lett.2000, 41, 3157-60.

 

Sinha, S.; Ilankumaran, P.; Chandrasekaran, S. “The prop-2-ynyloxy carbonyl function (POC):a new amino-protecting group removable from sulfur-containing peptides by ultrasonicirradiation with tetrathiomolybdate under mild and neutral conditions”. Tetrahedron Lett. 1999, 40, 771-774.

 

Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. “Diastereoselectivity in the reduction of acycliccarbonyl compounds with diisopropoxytitanium(III) tetrahydroborate”. J. Org. Chem. 1999, 64, 5841-5844.

 

Sinha, S.; Ilankumaran, P.; Chandrasekaran, S. “One pot conversion of alcohols to disulfides mediated by tetrathiomolybdate”. Tetrahedron. 1999, 55, 14769-14776.