Rodrigo L. O. R. Cunha | UFABC - Federal University of ABC (original) (raw)
Papers by Rodrigo L. O. R. Cunha
![Research paper thumbnail of Acetonyldichloro[( Z )-2-chloro-1-methyl-2-phenylethenyl]tellurium(IV)](https://attachments.academia-assets.com/46127500/thumbnails/1.jpg)
](Acta Crystallographica Section C Crystal Structure Communications, 1999
Acta Crystallographica Section C Crystal Structure Communications, 1999
Abstract The geometry around the TeTM atom in the title com-pound, C12H15C1302Te or [TeC12 (CsHsC... more Abstract The geometry around the TeTM atom in the title com-pound, C12H15C1302Te or [TeC12 (CsHsCIO)(C7HTO)], is pseudo-trigonal bipyramidal, with the C1 atoms in the apical positions and the Te lone pair occupying the fifth position in the equatorial plane. By including the intermolecular secondary Te.-. CI contact [3.485 (1),~] trans to the Te---Cvinyl bond, the structure may be regarded as pseudo-octahedral. The molecules are associated via an O--H... C1 hydrogen bond to form centrosymmetric dimeric units, which in turn are ...
Toxicology, 2015
Phenothiazine derivatives are neuroleptic drugs used in the treatment of schizophrenia and anxiet... more Phenothiazine derivatives are neuroleptic drugs used in the treatment of schizophrenia and anxiety. Several side effects are described for these drugs, including hepatotoxicity, which may be related to their cytotoxic activity. Working with isolated rat liver mitochondria, we previously showed that phenothiazine derivatives induced the mitochondrial permeability transition associated with cytochrome c release. Since the mitochondrial permeabilization process plays a central role in cell death, the aim of this work was to evaluate the effects of five phenothiazine derivatives (chlorpromazine, fluphenazine, thioridazine, trifluoperazine, and triflupromazine) on the viability of hepatoma tissue culture (HTC) cells to establish the structural requirements for cytotoxicity. All phenothiazine derivatives decreased the viability of the HTC cells in a concentration-dependent manner and exhibited different cytotoxic potencies. The EC 50 values ranged from 45 to 125 mM, with the piperidinic derivative thioridazine displaying the most cytotoxicity, followed by the piperazinic and aliphatic derivatives. The addition of the phenothiazine derivatives to cell suspensions resulted in significant morphological changes and plasma membrane permeabilization. Octanol/water partition studies revealed that these drugs partitioned preferentially to the apolar phase, even at low pH values ( 4.5). Also, structural and electronic properties were calculated employing density functional theory. Interestingly, the phenothiazine derivatives promoted an immediate dissipation of the mitochondrial transmembrane potential in HTC cells, and the EC 50 values were closely correlated with those obtained in cell viability assays, as well as the EC 50 for swelling in isolated mitochondria. These results significantly contribute to improving our understanding of the specific structural requirements of the phenothiazine derivatives to induce cell death and suggest the involvement of the mitochondrial permeability transition in phenothiazine-induced cytotoxicity in HTC cells.
Biotechnology advances, Jan 2, 2015
The kinetic resolution of racemates and desymmetrization are the most common approaches to the pr... more The kinetic resolution of racemates and desymmetrization are the most common approaches to the preparation of enantiomerically enriched compounds. These procedures allow the access of high valuable, chiral building blocks for many purposes in academic or industrial R&D endeavors. Nevertheless, the scope of stereochemistry recognition in biotransformations usually occurs at the site of the transformation or when it is close to it (not more than 3 bonds). However, there are a growing number of enzymatic transformations which surpass the limits of stereorecognition of remote chiral (or prochiral) centers. In this account, we would like to present some aspects of biocatalyzed remote resolutions and remote desymmetrizations to call attention for these challenging transformations.
Analytical Biochemistry, 2015
In the intraerythrocytic trophozoite stages of Plasmodium falciparum, the calcium-dependent cyste... more In the intraerythrocytic trophozoite stages of Plasmodium falciparum, the calcium-dependent cysteine protease calpain (Pf-calpain) has an important role in the parasite calcium modulation and cell development. We established specific conditions to follow by confocal microscopy and spectrofluorimetry measurements the intracellular activity of Pf-calpain in live cells. The catalytic activity was measured using the fluorogenic Z-Phe-Arg-MCA (where Z is carbobenzoxy and MCA is 4-methylcoumaryl-7-amide). The calmodulin inhibitor calmidazolium and the sarcoplasmic reticulum calcium ATPase inhibitor thapsigargin were used for modifications in the cytosolic calcium concentrations that persisted in the absence of extracellular calcium. The observed calcium-dependent peptidase activity was greatly inhibited by specific cysteine protease inhibitor E-64 and by the selective calpain inhibitor ALLN (N-acetyl-L-leucyl-L-leucyl-L-norleucinal). Taken together, we observed that intracellular Pf-calpain can be selectively detected and is the main calcium-dependent protease in the intraerythrocytic stages of the parasite. The method described here can be helpful in cell metabolism studies and antimalarial drug screening.
Natural Product Research, 2012
Bioactivity-guided fractionation of n-hexane phase from MeOH extract of the seeds of Cassia fistu... more Bioactivity-guided fractionation of n-hexane phase from MeOH extract of the seeds of Cassia fistula L. (Leguminosae) yielded two bioactive substances against Cladosporium cladosporioides and C. sphaerospermum. After spectroscopic analysis, these compounds were characterised as the known benzyl 2-hydroxy-3,6-dimethoxybenzoate and its dimer dibenzyl 2,2'-dihydroxy-3,6,3″,6″-tetramethoxy-biphenyl-1,1'-dicarboxylate, which showed a new structural arrangement.
A mitoc��ndria �� a organela respons��vel pela produ����o da maior quantidade de ATP na c��lula. ... more A mitoc��ndria �� a organela respons��vel pela produ����o da maior quantidade de ATP na c��lula. Al��m desta fun����o, a mitoc��ndria tamb��m desempenha um papel fundamental na morte celular, seja por apoptose ou por necrose. Estudos demonstram que a membrana interna mitocondrial, normalmente imperme��vel, torna-se perme��vel a solutos de peso molecular maior do que 1500 Da quando ocorre a abertura de um poro denominado de poro de transi����o de permeabilidade (PTP). A abertura deste poro se d�� de v��rias ...
Experimental parasitology, Nov 28, 2011
Leishmaniasis and Chagas' are parasitic protozoan diseases that affect the poorest populatio... more Leishmaniasis and Chagas' are parasitic protozoan diseases that affect the poorest population in the world, causing a high mortality and morbidity. As a result of highly toxic and long-term treatments, novel, safe and more efficacious drugs are essential. In this work, the CH2Cl2 phase from MeOH extract from the leaves of Baccharis retusa DC.(Asteraceae) was fractioned to afford two flavonoids: naringenin (1) and sakuranetin (2). These compounds were in vitro tested against Leishmania spp. promastigotes and amastigotes and ...
Bioorganic & Medicinal Chemistry, 2011
A new series of organotelluranes were synthesized and investigated, and the structure-activity re... more A new series of organotelluranes were synthesized and investigated, and the structure-activity relationships in cysteine proteases inhibition were determinated. It was possible to identify the relevance of structural components linked to the reactivity of these compounds as inhibitors. For example, dibromo-organotelluranes showed to be more reactive than dichloro-organotelluranes towards cysteine cathepsins V and S. Besides, no remarkable enantio-selectivity was verified. In general the achiral organotelluranes were more reactive than the chiral congeners against cysteine cathepsins V and S. A reactivity order for organochalcogenanes and cysteine cathepsins was proposed after the comparison of the inhibitory potencies of organotelluranes with the related organoselenanes.
Cheminform, 2007
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
Cheminform, 2007
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
A mitocôndria é a organela responsável pela produção da maior quantidade de ATP na célula. Além d... more A mitocôndria é a organela responsável pela produção da maior quantidade de ATP na célula. Além desta função, a mitocôndria também desempenha um papel fundamental na morte celular, seja por apoptose ou por necrose. Estudos demonstram que a membrana interna mitocondrial, normalmente impermeável, torna-se permeável a solutos de peso molecular maior do que 1500 Da quando ocorre a abertura de um poro denominado de poro de transição de permeabilidade (PTP).
PloS one, Nov 7, 2012
Tellurium compounds have shown several biological properties and recently the leishmanicidal effe... more Tellurium compounds have shown several biological properties and recently the leishmanicidal effect of one organotellurane was demonstrated. These findings led us to test the effect of the organotellurium compound RF07 on Leishmania (Leishmania) chagasi, the agent of visceral leishmaniasis in Latin America. In vitro assays were performed in L. (L.) chagasi-infected bone marrow derived macrophages treated with different concentrations of RF07. In in vivo experiments Golden hamsters were infected with L. (L.) chagasi and injected intraperitoneally with RF07 whereas control animals received either Glucantime or PBS. The effect of RF07 on cathepsin B activity of L. (L.) chagasi amastigotes was assayed spectrofluorometrically using fluorogenic substrates. The main findings were: 1) RF07 showed significant leishmanicidal activity against intracellular parasites at submicromolar concentrations (IC50 of 529.7626.5 nM), and the drug displayed 10fold less toxicity to macrophages (CC50 of 5,4266272.8 nM); 2) kinetics assays showed an increasing leishmanicidal action of RF07 at longer periods of treatment; 3) one month after intraperitoneal injection of RF07 L. (L.) chagasi-infected hamsters showed a reduction of 99.6% of parasite burden when compared to controls that received PBS; 4) RF07 inhibited the cathepsin B activity of L. (L.) chagasi amastigotes. The present results demonstrated that the tellurium compound RF07 is able to destroy L. (L.) chagasi in vitro and in vivo at concentrations that are non toxic to the host. We believe these findings support further study of the potential of RF07 as a possible alternative for the chemotherapy of visceral leishmaniasis.
PLoS Neglected Tropical Diseases, May 10, 2012
Background: Antitumor cyclopalladated complexes with low toxicity to laboratory animals have show... more Background: Antitumor cyclopalladated complexes with low toxicity to laboratory animals have shown leishmanicidal effect. These findings stimulated us to test the leishmanicidal property of one palladacycle compound called DPPE 1.2 on Leishmania (Leishmania) amazonensis, an agent of simple and diffuse forms of cutaneous leishmaniasis in the Amazon region, Brazil. Methodology/Principal Findings: Promastigotes of L. (L.) amazonensis and infected bone marrow-derived macrophages were treated with different concentrations of DPPE 1.2. In in vivo assays foot lesions of L. (L.) amazonensis-infected BALB/c mice were injected subcutaneously with DPPE 1.2 and control animals received either Glucantime or PBS. The effect of DPPE 1.2 on cathepsin B activity of L. (L.) amazonensis amastigotes was assayed spectrofluorometrically by use of fluorogenic substrates. The main findings were: 1) axenic L. (L.) amazonensis promastigotes were destroyed by nanomolar concentrations of DPPE 1.2 (IC50 = 2.13 nM); 2) intracellular parasites were killed by DPPE 1.2 (IC50 = 128.35 nM), and the drug displayed 10-fold less toxicity to macrophages (CC50 = 1,267 nM); 3) one month after intralesional injection of DPPE 1.2 infected BALB/c mice showed a significant decrease of foot lesion size and a reduction of 97% of parasite burdens when compared to controls that received PBS; 4) DPPE 1.2 inhibited the cysteine protease activity of L. (L.) amazonensis amastigotes and more significantly the cathepsin B activity.
Free Radical Biology …, Nov 2012
… of Molecular Structure, Jan 16, 2012
The crystallographically determined structure of biologically active 4,4-dichloro-1,3-diphenyl-4-... more The crystallographically determined structure of biologically active 4,4-dichloro-1,3-diphenyl-4-telluraoct-2-en-1-one, 3, shows the coordination geometry for Te to be distorted ψ-pentagonal bipyramidal based on a C2OCl3(lone pair) donor set. Notable is the presence of an intramolecular axial Te⋯O(carbonyl) interaction, a design element included to reduce hydrolysis. Raman and molecular modelling studies indicate the persistence of the Te⋯O(carbonyl) interaction in the solution (CHCl3) and gas-phases, respectively. Docking studies of 3′ (i.e. original 3 less one chloride) with Cathepsin B reveals a change in the configuration about the vinyl C► Tellurium compounds display pharmaceutical potential. ► Cathepsin B is a likely target for thiophilic tellurium. ► Intramolecular Te⋯O(carbonyl) contacts prevent hydrolysis. ► Tellurium forms a Te–S bond with Cathepsin B according to docking studies. ► Optimal ligand⋯Cathepsin B interactions rationalise differences in inhibition.
Acta Crystallographica Section C Crystal Structure Communications, 1999
Acta Crystallographica Section C Crystal Structure Communications, 1999
Abstract The geometry around the TeTM atom in the title com-pound, C12H15C1302Te or [TeC12 (CsHsC... more Abstract The geometry around the TeTM atom in the title com-pound, C12H15C1302Te or [TeC12 (CsHsCIO)(C7HTO)], is pseudo-trigonal bipyramidal, with the C1 atoms in the apical positions and the Te lone pair occupying the fifth position in the equatorial plane. By including the intermolecular secondary Te.-. CI contact [3.485 (1),~] trans to the Te---Cvinyl bond, the structure may be regarded as pseudo-octahedral. The molecules are associated via an O--H... C1 hydrogen bond to form centrosymmetric dimeric units, which in turn are ...
Toxicology, 2015
Phenothiazine derivatives are neuroleptic drugs used in the treatment of schizophrenia and anxiet... more Phenothiazine derivatives are neuroleptic drugs used in the treatment of schizophrenia and anxiety. Several side effects are described for these drugs, including hepatotoxicity, which may be related to their cytotoxic activity. Working with isolated rat liver mitochondria, we previously showed that phenothiazine derivatives induced the mitochondrial permeability transition associated with cytochrome c release. Since the mitochondrial permeabilization process plays a central role in cell death, the aim of this work was to evaluate the effects of five phenothiazine derivatives (chlorpromazine, fluphenazine, thioridazine, trifluoperazine, and triflupromazine) on the viability of hepatoma tissue culture (HTC) cells to establish the structural requirements for cytotoxicity. All phenothiazine derivatives decreased the viability of the HTC cells in a concentration-dependent manner and exhibited different cytotoxic potencies. The EC 50 values ranged from 45 to 125 mM, with the piperidinic derivative thioridazine displaying the most cytotoxicity, followed by the piperazinic and aliphatic derivatives. The addition of the phenothiazine derivatives to cell suspensions resulted in significant morphological changes and plasma membrane permeabilization. Octanol/water partition studies revealed that these drugs partitioned preferentially to the apolar phase, even at low pH values ( 4.5). Also, structural and electronic properties were calculated employing density functional theory. Interestingly, the phenothiazine derivatives promoted an immediate dissipation of the mitochondrial transmembrane potential in HTC cells, and the EC 50 values were closely correlated with those obtained in cell viability assays, as well as the EC 50 for swelling in isolated mitochondria. These results significantly contribute to improving our understanding of the specific structural requirements of the phenothiazine derivatives to induce cell death and suggest the involvement of the mitochondrial permeability transition in phenothiazine-induced cytotoxicity in HTC cells.
Biotechnology advances, Jan 2, 2015
The kinetic resolution of racemates and desymmetrization are the most common approaches to the pr... more The kinetic resolution of racemates and desymmetrization are the most common approaches to the preparation of enantiomerically enriched compounds. These procedures allow the access of high valuable, chiral building blocks for many purposes in academic or industrial R&D endeavors. Nevertheless, the scope of stereochemistry recognition in biotransformations usually occurs at the site of the transformation or when it is close to it (not more than 3 bonds). However, there are a growing number of enzymatic transformations which surpass the limits of stereorecognition of remote chiral (or prochiral) centers. In this account, we would like to present some aspects of biocatalyzed remote resolutions and remote desymmetrizations to call attention for these challenging transformations.
Analytical Biochemistry, 2015
In the intraerythrocytic trophozoite stages of Plasmodium falciparum, the calcium-dependent cyste... more In the intraerythrocytic trophozoite stages of Plasmodium falciparum, the calcium-dependent cysteine protease calpain (Pf-calpain) has an important role in the parasite calcium modulation and cell development. We established specific conditions to follow by confocal microscopy and spectrofluorimetry measurements the intracellular activity of Pf-calpain in live cells. The catalytic activity was measured using the fluorogenic Z-Phe-Arg-MCA (where Z is carbobenzoxy and MCA is 4-methylcoumaryl-7-amide). The calmodulin inhibitor calmidazolium and the sarcoplasmic reticulum calcium ATPase inhibitor thapsigargin were used for modifications in the cytosolic calcium concentrations that persisted in the absence of extracellular calcium. The observed calcium-dependent peptidase activity was greatly inhibited by specific cysteine protease inhibitor E-64 and by the selective calpain inhibitor ALLN (N-acetyl-L-leucyl-L-leucyl-L-norleucinal). Taken together, we observed that intracellular Pf-calpain can be selectively detected and is the main calcium-dependent protease in the intraerythrocytic stages of the parasite. The method described here can be helpful in cell metabolism studies and antimalarial drug screening.
Natural Product Research, 2012
Bioactivity-guided fractionation of n-hexane phase from MeOH extract of the seeds of Cassia fistu... more Bioactivity-guided fractionation of n-hexane phase from MeOH extract of the seeds of Cassia fistula L. (Leguminosae) yielded two bioactive substances against Cladosporium cladosporioides and C. sphaerospermum. After spectroscopic analysis, these compounds were characterised as the known benzyl 2-hydroxy-3,6-dimethoxybenzoate and its dimer dibenzyl 2,2'-dihydroxy-3,6,3″,6″-tetramethoxy-biphenyl-1,1'-dicarboxylate, which showed a new structural arrangement.
A mitoc��ndria �� a organela respons��vel pela produ����o da maior quantidade de ATP na c��lula. ... more A mitoc��ndria �� a organela respons��vel pela produ����o da maior quantidade de ATP na c��lula. Al��m desta fun����o, a mitoc��ndria tamb��m desempenha um papel fundamental na morte celular, seja por apoptose ou por necrose. Estudos demonstram que a membrana interna mitocondrial, normalmente imperme��vel, torna-se perme��vel a solutos de peso molecular maior do que 1500 Da quando ocorre a abertura de um poro denominado de poro de transi����o de permeabilidade (PTP). A abertura deste poro se d�� de v��rias ...
Experimental parasitology, Nov 28, 2011
Leishmaniasis and Chagas' are parasitic protozoan diseases that affect the poorest populatio... more Leishmaniasis and Chagas' are parasitic protozoan diseases that affect the poorest population in the world, causing a high mortality and morbidity. As a result of highly toxic and long-term treatments, novel, safe and more efficacious drugs are essential. In this work, the CH2Cl2 phase from MeOH extract from the leaves of Baccharis retusa DC.(Asteraceae) was fractioned to afford two flavonoids: naringenin (1) and sakuranetin (2). These compounds were in vitro tested against Leishmania spp. promastigotes and amastigotes and ...
Bioorganic & Medicinal Chemistry, 2011
A new series of organotelluranes were synthesized and investigated, and the structure-activity re... more A new series of organotelluranes were synthesized and investigated, and the structure-activity relationships in cysteine proteases inhibition were determinated. It was possible to identify the relevance of structural components linked to the reactivity of these compounds as inhibitors. For example, dibromo-organotelluranes showed to be more reactive than dichloro-organotelluranes towards cysteine cathepsins V and S. Besides, no remarkable enantio-selectivity was verified. In general the achiral organotelluranes were more reactive than the chiral congeners against cysteine cathepsins V and S. A reactivity order for organochalcogenanes and cysteine cathepsins was proposed after the comparison of the inhibitory potencies of organotelluranes with the related organoselenanes.
Cheminform, 2007
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
Cheminform, 2007
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
A mitocôndria é a organela responsável pela produção da maior quantidade de ATP na célula. Além d... more A mitocôndria é a organela responsável pela produção da maior quantidade de ATP na célula. Além desta função, a mitocôndria também desempenha um papel fundamental na morte celular, seja por apoptose ou por necrose. Estudos demonstram que a membrana interna mitocondrial, normalmente impermeável, torna-se permeável a solutos de peso molecular maior do que 1500 Da quando ocorre a abertura de um poro denominado de poro de transição de permeabilidade (PTP).
PloS one, Nov 7, 2012
Tellurium compounds have shown several biological properties and recently the leishmanicidal effe... more Tellurium compounds have shown several biological properties and recently the leishmanicidal effect of one organotellurane was demonstrated. These findings led us to test the effect of the organotellurium compound RF07 on Leishmania (Leishmania) chagasi, the agent of visceral leishmaniasis in Latin America. In vitro assays were performed in L. (L.) chagasi-infected bone marrow derived macrophages treated with different concentrations of RF07. In in vivo experiments Golden hamsters were infected with L. (L.) chagasi and injected intraperitoneally with RF07 whereas control animals received either Glucantime or PBS. The effect of RF07 on cathepsin B activity of L. (L.) chagasi amastigotes was assayed spectrofluorometrically using fluorogenic substrates. The main findings were: 1) RF07 showed significant leishmanicidal activity against intracellular parasites at submicromolar concentrations (IC50 of 529.7626.5 nM), and the drug displayed 10fold less toxicity to macrophages (CC50 of 5,4266272.8 nM); 2) kinetics assays showed an increasing leishmanicidal action of RF07 at longer periods of treatment; 3) one month after intraperitoneal injection of RF07 L. (L.) chagasi-infected hamsters showed a reduction of 99.6% of parasite burden when compared to controls that received PBS; 4) RF07 inhibited the cathepsin B activity of L. (L.) chagasi amastigotes. The present results demonstrated that the tellurium compound RF07 is able to destroy L. (L.) chagasi in vitro and in vivo at concentrations that are non toxic to the host. We believe these findings support further study of the potential of RF07 as a possible alternative for the chemotherapy of visceral leishmaniasis.
PLoS Neglected Tropical Diseases, May 10, 2012
Background: Antitumor cyclopalladated complexes with low toxicity to laboratory animals have show... more Background: Antitumor cyclopalladated complexes with low toxicity to laboratory animals have shown leishmanicidal effect. These findings stimulated us to test the leishmanicidal property of one palladacycle compound called DPPE 1.2 on Leishmania (Leishmania) amazonensis, an agent of simple and diffuse forms of cutaneous leishmaniasis in the Amazon region, Brazil. Methodology/Principal Findings: Promastigotes of L. (L.) amazonensis and infected bone marrow-derived macrophages were treated with different concentrations of DPPE 1.2. In in vivo assays foot lesions of L. (L.) amazonensis-infected BALB/c mice were injected subcutaneously with DPPE 1.2 and control animals received either Glucantime or PBS. The effect of DPPE 1.2 on cathepsin B activity of L. (L.) amazonensis amastigotes was assayed spectrofluorometrically by use of fluorogenic substrates. The main findings were: 1) axenic L. (L.) amazonensis promastigotes were destroyed by nanomolar concentrations of DPPE 1.2 (IC50 = 2.13 nM); 2) intracellular parasites were killed by DPPE 1.2 (IC50 = 128.35 nM), and the drug displayed 10-fold less toxicity to macrophages (CC50 = 1,267 nM); 3) one month after intralesional injection of DPPE 1.2 infected BALB/c mice showed a significant decrease of foot lesion size and a reduction of 97% of parasite burdens when compared to controls that received PBS; 4) DPPE 1.2 inhibited the cysteine protease activity of L. (L.) amazonensis amastigotes and more significantly the cathepsin B activity.
Free Radical Biology …, Nov 2012
… of Molecular Structure, Jan 16, 2012
The crystallographically determined structure of biologically active 4,4-dichloro-1,3-diphenyl-4-... more The crystallographically determined structure of biologically active 4,4-dichloro-1,3-diphenyl-4-telluraoct-2-en-1-one, 3, shows the coordination geometry for Te to be distorted ψ-pentagonal bipyramidal based on a C2OCl3(lone pair) donor set. Notable is the presence of an intramolecular axial Te⋯O(carbonyl) interaction, a design element included to reduce hydrolysis. Raman and molecular modelling studies indicate the persistence of the Te⋯O(carbonyl) interaction in the solution (CHCl3) and gas-phases, respectively. Docking studies of 3′ (i.e. original 3 less one chloride) with Cathepsin B reveals a change in the configuration about the vinyl C► Tellurium compounds display pharmaceutical potential. ► Cathepsin B is a likely target for thiophilic tellurium. ► Intramolecular Te⋯O(carbonyl) contacts prevent hydrolysis. ► Tellurium forms a Te–S bond with Cathepsin B according to docking studies. ► Optimal ligand⋯Cathepsin B interactions rationalise differences in inhibition.