Dr. José C. J. M. D. S. Menezes, completed his B.Sc (2000); M.Sc. (2002) and Ph.D (2009) from Goa University, India and worked on the synthesis of compounds derived from natural products for his PhD thesis. Since October 2010, he joined the organic chemistry and natural products (QOPNA) group with Prof. J.A.S. Cavaleiro at the Department of Chemistry, University of Aveiro, Portugal as a post-doctoral researcher. His research interests are synthesis of derivatives of natural compounds like Coumarins, Indanones, Flavonoids, Flavans; Drug design and application of synthesized compounds from naturally derived templates to biology are current research interests Synthesis of porphyrins, Chlorin e6, Protoporphyrin-IX and their derivatives and photophysical properties of these new porphyrin derivatives and their applications in photodynamic therapy (PDT) Structural analysis of compounds by mass spectrometry methods for application in biology. Fragmentation modes, and mechanistic pathways to determine fate of molecules when used in biological mediums.
Endereço de acesso a este CV: http://www.degois.pt/visualizador/curriculum.jsp?key=9902854333650317

Nome completo Full name	Jose Carlos Joaquim Maia De Souza Menezes
Nome em citações bibliográficas Quoting name	Menezes, J. C. J. M. D. S.
Domínio científico de atuação Scientific domain	Ciências Exactas-Química.

Endereço profissional Professional address

Universidade de Aveiro Departamento de Química Química Orgânica, Produtos Naturais e Agro-Alimentares - QOPNAA Departamento de Química, Universidade de Aveiro Aveiro 3810-193 Aveiro Portugal Correio electrónico: josemenezes@ua.pt Homepage: http://www.ua.pt/qopna/PageText.aspx?id=16726

Sexo Gender

Masculino»Male

2004-2009	Doutoramento Phd
Ph.D (5 anos » years) . Goa University, Department of Chemistry, Índia. Instituição portuguesa que atribuiu reconhecimento/equivalência/registo » Portuguese Instituition providing acknowledgement/equivalence/registry : Universidade de Aveiro. Com o tipo » With the type: Reconhecimento » Acknowledgement.

2000-2002	Mestrado Master degree
Master in Science (Chemistry) (2 anos » years) . Department of Chemistry, Índia. Instituição portuguesa que atribuiu reconhecimento/equivalência/registo » Portuguese Instituition providing acknowledgement/equivalence/registry : Universidade de Aveiro. Com o tipo » With the type: Reconhecimento » Acknowledgement.

1997-2000	Bacharelato Bachelor degree
Bachelor in Science (Chemistry) (3 anos » years) . Department of Chemistry, Índia. Instituição portuguesa que atribuiu reconhecimento/equivalência/registo » Portuguese Instituition providing acknowledgement/equivalence/registry : Universidade de Aveiro. Com o tipo » With the type: Reconhecimento » Acknowledgement.

2012	Curso de curta duração Short course
Photobiophysics. Universidade de Aveiro, Portugal.

2010-2010	Curso de curta duração Short course
Photobiophysics. Universidade de Aveiro, Portugal.

Universidade de Aveiro

Jun/2013-Actual

Outra Situação

Universidade de Aveiro

Mai/2011-Actual

Outra Situação

Universidade de Aveiro

Out/2010-Actual

Outra Situação

Neucon Pharma Pvt. Ltd.

Jan/2010-Ago/2010

Investigador-coordenador

Department of Chemistry

Fev/2004-Nov/2009

Outra Situação

Sumo Industries

Nov/2002-Jan/2004

Outra Situação

CIPLA

Jul/2002-Set/2002

Outra Situação

Participação como Investigador Participation as Researcher

2013- Síntese e caracterização de novas heteroaril-clorinas e avaliação biológica das suas potencialidades como agentes antitumorais -Synthesis and characterization of novel heteroaryl-chlorins and biological evaluation of their potential as anticancer agents

Referência do projeto»Project reference: Proc. No. 441.00 CNRST.

2011- Porfirinas e transformações de hetero-ciclo-adição com derivados naftoquinónicos: síntese de novos macrociclos

Referência do projeto»Project reference: PEst-C/QUI/UI0062/2011.

2011- Porfirinas e transformações de Buchwald-Hartwig aminação catalisada por paládio: síntese de novos macrociclos

Referência do projeto»Project reference: PEst-C/QUI/UI0062/2011.

2010- Porfirinas e transformações de hetero-ciclo-adição com derivados naftoquinónicos: síntese de novos macrociclos

Referência do projeto»Project reference: CAPES (Brazil)-FCT (Portugal) .

Compreende Understandig	Inglês (Bem), Outros (Bem), Português (Bem).
Fala Speaking	Inglês (Bem), Outros (Bem), Português (Bem).
Lê Reading	Inglês (Bem), Outros (Bem), Português (Bem).
Escreve Writing	Inglês (Bem), Outros (Bem), Português (Pouco).

Jan/2013 - Jun/2013	Portuguese Chemical Society, Membro.
Jan/2012 - Dez/2012	Portuguese Chemical Society, Membro.
Jan/2011 - Dez/2011	Portuguese Chemical Society, Membro.

Artigos em revistas com arbitragem científica Papers in periodics with scientific refereeing

1.	Santos, Carla I; Oliveira, Elisabete; Menezes, José C. M. S; Barata, Joana F; Faustino, M.Amparo F; Ferreira, Vitor F; Cavaleiro, José A; Neves, M.Graça P. S; Lodeiro, Carlos. 2014. "New coumarin-corrole and -porphyrin conjugate multifunctional probes for ANIONIC or CATIONIC interactions: Synthesis, spectroscopy and solid supported studies", Tetrahedron, 70: 3361 - 3370. Corroles and porphyrins are very promising probes to be used as materials for anion and metal ion detection. Here, we present the synthesis and characterization of two new corrole-coumarin derivatives 7-8 and some porphyrin-coumarin analogues 3-6. The sensing ability of the metalloconjugates was studied in the presence of spherical (F¯, Cl¯), linear (CN¯) and bulky anions (CH3COO¯). The porphyrin free-base conjugates were studied with Na+, Ca2+, Zn2+, Cd2+, Pb2+, Fe2+, Ba2+, Cu2+, Ag+ and Hg2+, showing a colorimetric effect (colour change from purple to yellow) and an unprecedented selectivity for Hg2+. The insertion of coumarin moiety confers an unusual solubility of these conjugates in ethanol. One of the porphyrin free-base conjugate was fully studied in a mixture EtOH:H2O (50:50) and showed a similar behaviour with Hg2+. Under these conditions, the conjugate presented a higher association constant than in toluene and was able to detect and quantify a minimal amount of 0.6 ppm and 1.2 ppm of Hg2+, respectively. Having in mind the biological and environmental application of these conjugates, non-expensive solid supports, like agarose and natural cellulose polymers were developed. In the cellulose support material (filter paper) the colorimetric effect for Hg2+ reveals a similar behaviour as in solution. In addition pH studies carried out with the same conjugate showed a green colour at low pH and a yellow colour at high pH values in solution and in solid supports. .

2.	Mesquita, Mariana Q; Menezes, José C; Neves, Maria G; Tomé, Augusto C; Cavaleiro, José A; Cunha, Ângela; Almeida, Adelaide; Hackbarth, Steffen; Röder, Beate; Faustino, M. A. F. 2014. "Photodynamic inactivation of bioluminescent Escherichia coli by neutral and cationic pyrrolidine-fused chlorins and isobacteriochlorins", Bioorganic & Medicinal Chemistry Letters 24, 3: 808 - 812. Photodynamic inactivation of bioluminescent E. coli in the presence of cationic chlorin and isobacteriochlorin photosensitizers (PSs) obtained from 5,10,15,20-tetrakis(pentafluorophenyl)-porphyrin is described. The spectroscopic data for the neutral and cationic derivatives and their photophysical characterizations, especially fluorescence and singlet oxygen generation capacity are also reported. The results show that there is a direct relation between the inactivation efficiency and the increasing number of charges on the molecules. The combined effect of higher wavelength absorption and number of positive charges on the PS shows a 6.1 log reduction during the inactivation process. Overall this study shows that the cationic isobacteriochlorin has high potential to be used as PS for the inactivation of Gram (-) bacteria.

3.	Fujita, Hideaki; Menezes, José C. J. M. D. S; Santos, Sérgio M; Yokota, Sadaki; Kamat, Shrivallabh P; Cavaleiro, José A. S; Motokawa, Tomonori; Kato, Tomomi; Mochizuki, Mayu; Fujiwara, Toshiyuki; Fujii, Yuki; Tanaka, Yoshitaka. 2014. "Inulavosin and its benzo-derivatives, melanogenesis inhibitors, target the copper loading mechanism to the active site of tyrosinase", Pigment Cell & Melanoma Research, XX: n/a - n/a. Tyrosinase, a melanosomal membrane protein containing copper, is a key enzyme for melanin synthesis in melanocytes. Inulavosin inhibits melanogenesis by enhancing a degradation of tyrosinase in lysosomes. However, the mechanism by which inulavosin redirects tyrosinase to lysosomes is yet unknown. The analyses of structure-activity relationship of inulavosin and its benzo-derivatives reveal that the hydroxyl and the methyl groups play a critical role in their inhibitory activity. Intriguingly, the docking studies to tyrosinase suggest that the compounds showing inhibitory activity bind through hydrophobic interactions to the cavity of tyrosinase below which the copper binding sites are located. This cavity is proposed to be required for the association with a chaperon that assists in copper loading to tyrosinase in Streptomyces antibioticus. Inulavosin and its benzo-derivatives may compete with the copper chaperon and result in a lysosomal mistargeting of apo-tyrosinase that has a conformational defect.

4.	Mesquita, Mariana Q; Menezes, José C; Pires, Sónia M; Neves, Maria G; Simões, Mário M; Tomé, Augusto C; Cavaleiro, José A; Cunha, Ângela; Daniel-da-Silva, Ana L; Almeida, Adelaide; Faustino, M. A. F. 2014. "Pyrrolidine-fused chlorin photosensitizer immobilized on solid supports for the photoinactivation of Gram negative bacteria", Dyes and Pigments 110, 110: 123 - 133. The emergence of resistant microorganism to conventional therapeutics prompted us to search new and better antimicrobial treatment modalities. In this work was envisaged an economically viable and environmental friendly approach to allow successive recovery and removal of the photosensitizer agent after photodynamic treatment. The photodynamic inactivation of bioluminescent E. coli in the presence of an immobilized cationic chlorin photosensitizer and its reusability are described. The chlorin photosensitizer (PS) was immobilized on two commercial materials: a 3-bromopropyl-functionalized silica and a Merrifield resin. The new photosensitising materials were characterized by UV-vis spectroscopy, SEM and EDX. Their singlet oxygen generation capacities were also assessed. Previous studies showed that there is a direct relationship between the photoinactivation efficiency and the number of positive charges on such PS molecules. Therefore the number of positive charges on the new prepared materials was further increased by treatment of the PS-immobilized materials with 1-methylimidazole and pyridine. The efficiency of photoinactivation against bioluminescent E. coli was evaluated in the presence of the non-immobilized chlorin (20 µM) as well as in the presence of the new prepared materials positively charged or non-charged on surface (20-200 µM) with white light at an irradiance of 4.0 mW.cm-2. Overall, this study shows that the materials resulting from the immobilization of the chlorin on the silica surface and on the Merrifield resin, and further modified with pyridine, have high potential to be used as PS for the inactivation of Gram negative bacteria (3.0 log reductions) and are able to maintain its antimicrobial efficiency after at least 3 repeated cycles of photoinactivation. Their reusability, without loss of effectiveness, confirms a potential inexpensive and friendly application in clinic and environmental areas.

5.	Orlikova, Barbora; Menezes, José C; Ji, Seungwon; Kamat, Shrivallabh P; Cavaleiro, José A; Diederich, Marc. 2014. "Methylenedioxy flavonoids: Assessment of cytotoxic and anti-cancer potential in human leukemia cells", European Journal of Medicinal Chemistry 84, 84: 173 - 180. A new series of chalcones, flavanones and flavones with methylenedioxy group at the 3',4' position in chalcone, 7,8 position in flavanones and flavones with mono-, di- and trimethoxy groups in the benzaldehyde ring have been assessed for their effect on proliferation, cytotoxic potential and apoptosis in human leukemia cells. Among the tested compounds, the chalcone series showed the best activity and chalcone 3 (mono methoxy group at the ortho position in A-ring) showed a significant effect on down-regulation of cancer cell proliferation and viability in three different leukemia cell lines (K562, Jurkat, U937). The executioner caspase cleavage analyses indicated that the cytotoxic effect mediated by chalcone 3 is due to induction of apoptotic cell death. Interestingly, the cytotoxic effect was cell type-specific and targeted preferentially cancer cells as peripheral blood mononuclear cells (PBMCs) from healthy donors were less affected by the treatment compared to K562, Jurkat and U937 leukemia cells. Altogether our results indicate a potential drug candidate with interesting differential toxicity obeying Lipinski's rule of five.

6.	Menezes, José C. J. M. D. S; Faustino, M. A. F; de Oliveira, K. T; Uliana, Marciana P; Ferreira, Vitor F; Hackbarth, Steffen; Röder, Beate; Teixeira Tasso, T; Furuyama, Taniyuki; Kobayashi, Nagao; Silva, Artur M. S; Neves, M. G. P. M. S; Cavaleiro, José A. S. 2014. "Synthesis of New Chlorin e6 Trimethyl and Protoporphyrin IX Dimethyl Ester Derivatives and Their Photophysical and Electrochemical Characterizations ", Chemistry - A European Journal, xx: n/a - n/a. In view of increasing demands for efficient photosensitizers for photodynamic therapy (PDT), this paper reports the synthesis and photophysical characterizations of new chlorin e6 trimethyl ester and protoporphyrin-IX dimethyl ester dyads as free-bases and Zn(II) complexes. The synthesis of these molecules linked at the -pyrrolic positions to pyrano[3,2-c]coumarin, pyrano[3,2-c]quinolinone and pyrano[3,2-c]naphthoquinone moieties was performed by using the domino Knoevenagel hetero Diels-Alder reaction. The a-methylenechromanes, a-methylenequinoline and ortho-quinone methides were generated in situ from Knoevenagel reaction respectively of 4-hydroxycoumarin, 4-hydroxy-6-methylcoumarin, 4-hydroxy-N-methylquinolinone and 2-hydroxy-1,4-naphthoquinone with paraformaldehyde in dioxane. All the dyads as free-bases and as Zn(II) complexes were obtained in high yields. All new compounds were fully characterized by 1D and 2D NMR techniques, UV-Vis and HRMS. Their photophysical properties were evaluated by measuring the fluorescence, singlet oxygen quantum yield by luminescence detection and also the triplet lifetimes were correlated by flash photolysis and intersystem crossing (ISC) rates. The fluorescence lifetimes were measured by time correlated single photon count (TCSPC) method, fluorescence decay associated spectra (FDAS) and anisotropy measurements. Magnetic circular dichroism (MCD) and circular dichroism (CD) spectra were recorded for one Zn(II) complex in order to obtain information, respectively, on the electronic and conformational states, and interpretation of these spectra was enhanced by molecular orbital (MO) calculations. Electrochemical studies of the Zn(II) complexes were also carried out to gain insights into their behavior for such applications.

7.	Menezes, José C. J. M. D. S; Cavaleiro, José A. S; Kamat, Shrivallabh P; Barros, Cristina M. R. F; Domingues, M. R. M. 2013. "Electrospray tandem mass spectrometry analysis of methylenedioxy chalcones, flavanones and flavones", Rapid Communications in Mass Spectrometry 27, 12: 1303 - 1310. Rationale- Several methylenedioxy chalcones, flavanones and flavones substituted with mono-, di- and tri-methoxy groups have been used in treatment of proliferative condition like cancer and inflammatory diseases. The application of these flavonoids in biology requires an analytical method to ensure a detailed knowledge of their structures after drug metabolism. Method- ESI-MS and tandem mass spectra were acquired using a Q-TOF 2 instrument. Fragmentation patterns and their pathways were analyzed by CID-MS2-3 spectra acquired in a LXQ linear ion trap mass spectrometer using standard isolation and excitation procedures (activation q value of 0.25, activation time of 30 ms). ESI-MS and ESI-MSn conditions: spray voltage 5 kV, nitrogen 8.00 sheath gas flow rate (arb), heated capillary temperature 275 °C, capillary voltage 10.99 V; tube lens voltage 75.01 V. Results- The ESI-MS/MS of chalcones were nearly identical to their corresponding isomeric flavanones with 0,¿A+/1,3A+ and 0,1'B+/1,4B+ cleavages. Other common losses are of •CH3, H2O, HCHO and C2H2O. The characteristic loss of C2H2O and absence of 0,¿B+/1,3B+ product ion allows to distinguish between the 2- or 4-methoxy substituted chalcones and flavanones. Common losses of •CH3, •CH3 and •H, and C2H2O2 characteristic for the presence of methylenedioxy group were observed in flavones. Conclusions- The substitution pattern on the B ring leads to distinct base peaks formation in the flavones. In addition, differentiation of isomers with methoxy substituents in ortho and para positions of B ring was achieved using MS/MS in chalcones and flavanones. This method will be helpful for identification of these compounds in biological mixtures. .

8.	Menezes, José C; Neves, M. G. P; Cavaleiro, José A; Barros, Cristina; Santos, Sérgio M; da Silva, F. C; Ferreira, Vitor F; Domingues, M. R. M. 2013. "Gas phase reactions of beta-substituted hetero-Diels–Alder adducts of meso-tetraphenylporphyrin using tandem mass spectrometry", International Journal of Mass Spectrometry 343, 344: 1 - 8. Beta-substitued-meso-tetraphenylporphyrins with 5,10-dioxobenzo[g]- or 5,6-dioxobenzo[h]chromene, pyrano[3,2-c]coumarin and benzopyran moieties and the corresponding Zn(II), Cu(II) and Ni(II) complexes were studied by electrospray mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS). These heterocyclic moieties have well established pharmacological activities and as such the introduction of these motifs into the ß-pyrrolic position of the porphyrin macrocycle can alter the properties of the macrocycle and can produce new molecules with dual functions. The free base and Zn(II) complexes showed, in the ESI-MS spectra, the [M+H]+ ions while the Cu(II) and Ni(II) complexes showed the M+• ions. The [M+H]+ and M+• ions were induced to fragment and the corresponding ESI tandem mass spectra (MS/MS) were analyzed. The main fragmentation mechanism occurs in general via the retro hetero-Diels-Alder pathway while unexpected fragmentations or rearrangements were observed principally with the Zn(II) complexes. The analysis of the fragmentation pattern of all complexes indicates that the presence or absence of the carbonyl function in the ß-substituent led to the formation of secondary fragments. The differentiation of the isomers 2a and 2b was only possible by comparison of their MS/MS spectra.

9.	Lopes, Sónia P; Menezes, José C; Hackbarth, Steffen; Pinto, Diana C; Faustino, Maria A; Silva, Artur M; Neves, Maria G; Röder, Beate; Cavaleiro, José A. 2013. "New flavonoid-porphyrin conjugates via Buchwald-Hartwig amination: Synthesis and photophysical studies", Tetrahedron Letters, 54: 00 - 00. New flavonoid-porphyrin conjugates were synthesized using the cross-coupling Buchwald-Hartwig amination for coupling of flavonoid and porphyrin moieties. A unique di-substituted flavone–porphyrin conjugate was also synthesized under similar reaction conditions for the first time. All the conjugates were fully characterized by NMR spectroscopy. The photophysical properties namely fluorescence and singlet oxygen production were evaluated considering their use for photodynamic therapy applications.

10.	Menezes, José C. J. M. D. S; Cavaleiro, José A. S; Domingues, M. R. M. 2013. "Structural analysis of 2-arylidene-1-indanone derivatives by electrospray ionization tandem mass spectrometry", Rapid Communications in Mass Spectrometry 27, 21: 2461 - 2471. Rationale- 2-arylidene-4-methoxy (or hydroxy)-7-methyl-1-indanone derivatives inspired from donepezil, the current drug used for the treatment of Alzheimer disease as inhibitor of acetylcholinesterase (AChE), were studied for the first time by electrospray mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS). Structurally these arylidene-indanone compounds are considered as cyclic analogues of chalcones. Method- ESI-MS and tandem mass spectra were acquired using a Q-TOF 2 instrument. Fragmentation patterns were analyzed by CID-MS2-3 spectra acquired in a Q-TOF and in LXQ linear ion trap mass spectrometers using standard isolation and excitation procedures. Results- All the 2-arylidene indanones have shown a common fragmentation pathway leading to a (21, 1')A+ product ion at m/z 187 and the retro-aldol product ion [(2, 21)B+] that allow to establish the substitution in the B ring. The effect of electron donating and withdrawing substituents on these fragmentation pathways was noticed. The presence of the OCH3, OH, NO2 and Br substituents gave typical fragmentation processes that allowed their unequivocal fingerprinting. The combined loss of the ortho substituent in the B-ring plus hydrogen (H, OCH3, Br and F) is proposed to form a stable cyclic ring product. Conclusions- Arylidene indanones with different substituents on the B ring are associated with a specific fragmentation pattern. In addition, differentiation between isomers with substituents in B ring at ortho and para positions were achieved using ESI-MS/MS. These fragmentation pathways can be used to further identify and determine the fate of these molecules in all stages of drug discovery. .

11.	Srinivasan, B. R; Raghavaiah, P.; Shirsat, R. N; Menezes, J. C. J. M. D. S; Kamat, S. P. 2012. "Single crystal X-ray analysis of isomeric 2-(2,4,4-trimethyl-3,4-dihydro-2h-benzo[h]× chromen-2-yl)-1-naphthyl acetate and 3-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[g]× chromen-2-yl)-2-naphthyl acetate", Journal of Structural Chemistry 53, 5: 943 - 947. Single crystal X-ray structure characterization of isomeric 2-(2,4,4-trimethyl-3,4-dihydro-2Hbenzo[ h]chromen-2-yl)-1-naphthyl acetate (1) and 3-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[g]chromen-2- yl)-2-naphthyl acetate (2) is described. Compound 1 crystallizes in the centrosymmetric monoclinic space group P21/c with all atoms situated in general positions. Isomeric compound 2 crystallizes in the centrosymmetric triclinic space group P-1 and its structure consists of two crystallographically independent molecules with all atoms located in general positions. In addition to intramolecular C–H¿O bonding, 2 is involved in two intermolecular C–H¿O interactions resulting in a one-dimensional H-bonded network.

12.	Krishna, Rahul; Titus, Elby; Costa, Luís C; Menezes, José C. J. M. D. S; Correia, Maria R. P; Pinto, Sara; Ventura, João; Araújo, J. P; Cavaleiro, José A. S; Gracio, José J. A. 2012. "Facile synthesis of hydrogenated reduced graphene oxide via hydrogen spillover mechanism", Journal of Materials Chemistry 22, 21: 10457 - 10457. Here we demonstrate a single step approach for the facile reduction of graphene oxide (GO) to hydrogenated reduced graphene oxide (HRGO) under ambient conditions.

13.	Menezes, José C. M. S; Pereira, Ana M. M; Neves, Maria G. M; Silva, Artur M; Santos, Sérgio M; Martinez, Sabrina T; Silva, Bárbara V; Pinto, Ângelo C; Cavaleiro, José A. 2012. "Synthesis of porphyrin indolin-2-one conjugates via palladium-catalyzed amination reactions", Tetrahedron, 68: 8330 - 8339. New porphyrin indolin-2-one conjugates were synthesized via palladium-catalyzed amination reactions of iodinated and dibrominated indolin-2-one derivatives with (2-amino-5,10,15,20-tetraphenylporphyrinato)nickel(II). The combination of palladium catalysts and the phosphine ligand dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) is an effective methodology for catalyzing the coupling of 5-iodo-, 5,7-dibromo- and 4,6-dibromo-1,3,3-trimethylindolin-2-one with 2-aminoporphyrin to give the corresponding mono-(2-aminoporphyrinyl)- and di-(2-aminoporphyrinyl)-substituted indolin-2-ones in satisfactory yields under mild conditions. The mono brominated porphyrinic derivatives also underwent cross-coupling reactions under similar catalytic conditions. The studies also demonstrated that the course of the coupling process depends on factors such as the catalytic system, number and position of the halogen substituents and the heating condition. Insights into the reactivity trends of the 5-iodo; 4,6- and 5,7-dibrominated indolin-2-one derivatives was carried out using theoretical calculations performed using density-functional theory with the B3LYP functional.

14.	Menezes, Jose C; Kamat, Shrivallabh P; Cavaleiro, Jose A; Gaspar, Alexandra; Garrido, Jorge; Borges, Fernanda. 2011. "Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates", European Journal of Medicinal Chemistry 46, 2: 773 - 777. Long chain alkyl hydroxycinnamates (8-21) were synthesized from the corresponding half esters of malonic acid (5-7) and benzaldehyde derivatives by Knoevenagel condensation. The total antioxidant capacity of these hydroxycinnamyl esters was evaluated using DPPH and ABTS assays. The observed antioxidant activity was highest for esters of caffeic acid followed by sinapic esters and ferulic esters. The parameters for drug-likeness of these hydroxycinnamyl esters were also evaluated according to the Lipinski’s ‘rule-of-five’. All the ester derivatives were found to violate one of the Lipinski’s parameters (cLogP >5), even though they have been found to be soluble in protic solvents. The predictive topological polar surface area (TPSA) data allow concluding that they could have a good capacity for penetrating cell membranes. Therefore, one can propose these novel lipophilic compounds as potential antioxidants for tackling oxidative processes.

15.	Menezes, Jose C. J. M. D. S; Srinivasan, Bikshandarkoil R; Raghavaiah, Pallepogu; Paknikar, Shashikumar K; Kamat, Shrivallabh P. 2011. "First synthesis of 2-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[h]chromen-2-yl)-1-naphthol and 3-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[g]chromen-2-yl)-2-naphthol from 1- and 2-naphthol derivatives", Journal of Heterocyclic Chemistry 48, 4: 952 - 956. Two new structurally isomeric, 2-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[h]chromen-2-yl)-1-naphthol (1) and 3-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[g]chromen-2-yl)-2-naphthol (3) have been synthesized from 2-acetyl-1-naphthol and ethyl-3-hydroxy-2-naphthoate, respectively, involving Grignard reaction, dehydration of the corresponding tertiary alcohols, and hetero Diels–Alder dimerization. The two benzochromenes (1 and 3) have been fully characterized by IR, NMR, and HRESIMS data. Their structures are further supported by crystallography of their corresponding acetates (2 and 4).

16.	Menezes, José; Gomes, Ana; Silva, Artur; Faustino, Maria; Neves, Maria; Tomé, Augusto; de C. S. F; Ferreira, Vitor; Cavaleiro, José. 2011. "Reaction of ß-Vinyl-meso-tetraphenylporphyrin with o-Quinone Methides", Synlett 2011, 13: 1841 - 1844. The hetero-Diels-Alder reaction of ß-vinyl-meso-tetraphenylporphyrinatozinc(II) with quinone methides generated in situ from Knoevenagel reaction of 2-hydroxy-1,4-naphthoquinone, 4-hydroxycoumarin and 4-hydroxy-6-methylcoumarin with paraformaldehyde and directly from ortho-hydroxybenzyl alcohol derivatives is reported.

17.	Menezes, Jose C; Kirtany, Janardan K; Kamat, Shrivallabh P. 2010. "Synthesis of 7,8-methylenedioxy-4'-methoxyisoflavone from <I>Indigofera linnaei</I> and two new related flavonoids", Journal of Chemical Research 34, 1: 28 - 29. The synthesis of naturally occurring 7,8-methylenedioxy-4’-methoxyisoflavone and 7,8-methylenedioxy-4’-methoxyflavone from 2’-hydroxy-3’,4’-methylenedioxy-4-methoxychalcone via the intermediacy of 7,8-methylenedioxy-4’- methoxyflavanone using thallium(III) acetate and catalytic amount of perchloric acid is reported. The products flavanone and the flavone are new flavonoids characterised by spectral analysis.

18.	Kamat, Shrivallabh P; Menezes, Jose C. J. M. D. S; Siddhaye, Bhushan M; Paknikar, Shashikumar K. 2008. "Facile syntheses of 4-hydroxy-7-methyl-1-indanone, isolated from cyanobacterium Nostoc commune", INDIAN JOURNAL OF CHEMISTRY, SEC-B 47, B: 1597 - 1599. Two different high yielding synthetic routes both starting with 6-methylcoumarin 2 have been described to prepare 4-hydroxy-7-methyl-1-indanone 1, a constituent of cyanobacterium Nostoc commune having antibacterial activity. In the first route, methylative lactone ring opening of the coumarin 2 followed by catalytic hydrogenation of the cinnamyl double bond and subsequent PPA cyclization gives the methyl ether 5 of 1 which on demethylation gives 1 in excellent yield. Alternatively, catalytic hydrogenation of 2 followed by fusion with anhydrous AlCl3 gives high yield of 1 in just two steps. JCR Impact factor (2011)- 0.689.

Apresentação oral de trabalho Oral work presentation

1.

Menezes, Jose C. J. M. D. S; Faustino, Maria A. F; Oliveira, Kleber T.; Silva, Artur M; Ferreira, Vitor F; Neves, M. G. P; Röder, Beate; Cavaleiro, José A. New chlorin e6 trimethyl ester derivatives via domino Knoevenagel hetero-Diels-Alder reaction: Synthesis and photophysical studies,XXIII Encontro Nacional da Sociedade Portuguesa de Química, Universidade de Aveiro, 12-14 June 2013,Aveiro 3810-193,2013 (Poster).

2.

Menezes, J. C. J. M. D. S; Faustino, Maria A. F; Oliveira, Kleber T.; Silva, Artur M; Ferreira, Vitor F; Neves, M. G. P; Röder, Beate; Cavaleiro, José A. S. Synthesis and photophysical studies of new chlorin e6 trimethyl ester derivatives,15th Congress of the European Society for Photobiology, 2-6 September 2013,Liège, Belgium,2013 (Poster).

3.

Fujita, Hideaki; Menezes, J. C. J. M. D. S; Santos, Sérgio M; Yokota, Sadaki; Kamat, Shrivallabh P; Cavaleiro, José A. S; Motokawa, Tomonori; Kato, Tomomi; Mochizuki, Mayu; Tanaka, Yoshitaka. Inulavosin and its benzo-derivatives, melanogenesis inhibitors, targets the copper loading mechanism to the active site of tyrosinase,The 86th Annual Meeting of the Japanese Biochemical Society, Yokohama, Japan, September 11-13, 2013,Yokohama, Japan,2013 (Poster).

4.

Mesquita, Mariana; Menezes, Jose C. J. M. D. S; Neves, M. G. P; Tomé, Augusto; Cavaleiro, José A; Cunha, Ângela; Almeida, Adelaide; Faustino, Maria A. F. Neutral and cationic chlorin and isobacteriochlorin derivatives of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin on the photodynamic inactivation of bioluminescent E. coli,XXIII Encontro Nacional da Sociedade Portuguesa de Química, Universidade de Aveiro, 12-14 June 2013,3810-193 Aveiro,2013 (Poster).

5.

Mesquita, Mariana; Menezes, J. C. J. M. D. S; Neves, M. G. P; Tomé, Augusto; Cavaleiro, José A. S; Cunha, Ângela; Almeida, Adelaide; Faustino, Maria A. F. Isobacteriochlorin derivative of 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin on the photodynamic inactivation of bioluminescent E. coli, 10º Portuguese National Meeting of Organic Chemistry and the 1st Portuguese-Brazilian Organic Chemistry Symposium, 4-6 September 2013,Lisbon,2013 (Poster).

6.

Mesquita, Mariana; Menezes, J. C. J. M. D. S; Faustino, Maria A. F; Neves, M. G. P; Cavaleiro, José A. S; Cunha, Ângela; Almeida, Adelaide. Photodynamic inactivation of bioluminescent E. coli by immobilized chlorin derivatives,15th Congress of the European Society for Photobiology, 2-6 September 2013,Liège, Belgium,2013 (Poster).

7.	Pereira, Ana M. V. M; Menezes, J. C. J. M. D. S; Faustino, Maria A. F; Neves, M. G. P; Tomé, Augusto; Silva, Artur M; Cavaleiro, José A. S. Amino porphyrins: In search of high valued tetrapyrrolic macrocycles,Research Day at University of Aveiro, 19 June 2013,Aveiro,2013 (Poster).

8.

Menezes, Jose C. J. M. D. S; Pereira, Ana M. V. M; Neves, Maria; Silva, Artur; Martinez, Sabrina T; Silva, Bárbara V; Pinto, Ângelo C; Cavaleiro, José A. S. Synthesis of Porphyrin Indolin-2-one Conjugates via Palladium-Catalyzed Amination Reactions,6th Spanish Portuguese Japanese Organic Chemistry Symposium/6SPJOCS, July 18-20,Lisbon,2012 (Poster).

9.

Fujita, Hideaki; Menezes, Jose C. J. M. D. S; Kamat, Shrivallabh P; Cavaleiro, José A. S; Tanaka, Yoshitaka. Characterization of the minimum structure of inulavosin required for the melanogenesis inhibitory activity,Kyushu University (Graduate School of Pharmaceutical Sciences)-Pusan University (College of Pharmacy) Joint Seminar, September 7,Fukuoka,2012 (Poster).

10.

Fujita, Hideaki; Menezes, Jose C. J. M. D. S; Kamat, Shrivallabh P; Cavaleiro, José A. S; Tanaka, Yoshitaka. Characterization of the minimum structure of inulavosin required for the melanogenesis inhibitory activity,The 85th Annual Meeting of the Japanese Biochemical Society, Fukuoka, Japan, December 14-16,Fukuoka,2012 (Poster).

11.

Menezes, Jose C. J. M. D. S; Fujita, Hideaki; Yokota, Sadaki; Kamat, Shrivallabh P; Cavaleiro, José A. S; Tanaka, Yoshitaka. Synthesis and melanogenesis inhibitory activity of 2-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[h]chromen-2-yl)-1-naphthol & 3-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[g]chromen-2-yl)-2-naphthol and their acetates,3rd Portuguese Meeting on Medicinal Chemistry, November 28-30,Aveiro,2012 (Poster). Melanosome is a highly specialized organelle where melanin is synthesized. Tyrosinase and tyrosinase-related protein-1 (Tyrp1) are major melanosomal membrane proteins and key enzymes for melanin synthesis in melanocytes. Inulavosin 1, a melanogenesis inhibitor isolated from Inula nervosa (Compositae), reduced the melanin content without affecting either the enzymatic activities or the transcription of tyrosinase or Tyrp1 in B16 melanoma cells. Inulavosin inhibited melanogenesis as a result of mistargeting of tyrosinase to lysosomes where it gets degraded [1]. Two new structurally isomeric, 2-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[h]chromen-2-yl)-1-naphthol (2) & 3-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[g]chromen-2-yl)-2-naphthol (4) have been synthesized [2] using the inulavosin molecule as template. The two benzochromenes (2 & 4) have been fully characterized by IR, NMR and HRESIMS data. Their structures are further supported by X-ray crystallographic studies of their corresponding acetates (3 & 5) [3]. All the four compounds (2-5) effectively inhibited melanogenesis to the same extent as inulavosin. The substituents influence on the inulavosin type compounds required for the inhibitory activity and the results already obtained will be presented .

12.

Santos, Carla I. M; Menezes, Jose C. J. M. D. S; Oliveira, Elisabete; Faustino, Maria A. F; Ferreira, Vitor; de C. S. F; Cavaleiro, José A. S; Neves, Maria G. M; Lodeiro, Carlos. New emissive porphyrins containing a coumarin unit selective for Hg(II) detection: Fluorescence studies,Natural products and related redox catalysts: Basic research and applications in medicine and agriculture (RedCat), University of Aveiro, November 25-27,Aveiro,2012 (Poster).

13.

Menezes, Jose C. J. M. D. S; Pereira, Ana M. V. M; Neves, Maria G. M; Silva, Artur M; Martinez, Sabrina T; Silva, Bárbara V; Pinto, Ângelo C; Cavaleiro, José A. S. Synthesis of Porphyrin Indolin-2-one Conjugates via Palladium-Catalyzed Amination Reactions,5th Annual meeting of QOPNA research group, University of Aveiro, 18 May ,Aveiro,2012 (Comunicação).

14.

Menezes, Jose C. J. M. D. S; Gomes, Ana; Silva, Artur; Faustino, Maria; Neves, Maria; Tomé, Augusto; de C. S. F; Ferreira, Vitor; Cavaleiro, José A. S. Reaction of ß-Vinyl-meso-tetraphenylporphyrin with ortho-Quinone Methides,XXII National Meeting of Portuguese Chemical Society, 3-6 July ,Braga,2011 (Comunicação).

15.

Menezes, Jose C. J. M. D. S; Gomes, Ana; Silva, Artur; Faustino, Maria; Neves, Maria; Tomé, Augusto; de C. S. F; Ferreira, Vitor; Cavaleiro, José A. S. Reaction of ß-Vinyl-meso-tetraphenylporphyrin with ortho-Quinone Methides- Synthesis and photophysical properties,XVII Encontro Luso-Galego de Química, 9-11 November ,Pontevedra, Spain,2011 (Poster).

16.	Menezes, Jose C. J. M. D. S; Kamat, Shrivallabh P. A simple two-step synthesis of naturally occurring biologically active cinnamyl esters,Royal Society of Chemistry,West India Section Ph.D Students Symposium, 19-20 October ,Panaji Goa,2007 (Comunicação).

Organização de evento Event organization

1.	Menezes, Jose C. J. M. D. S. Royal Society of Chemistry,West India Section Ph.D Students Symposium,2007 (Simpósio / Organização). Assisted main Coordinator for organizing Royal Society of Chemistry,West India Section Ph.D Students Symposium, October 19 & 20, 2007 held at Goa University.

Orientações Orientations

Participação editorial em revistas Magazine editorial participation

Orientações Orientations

Dissertação de Mestrado Master degree dissertation

Em curso Ongoing

1.	Mariana Mesquita, Novos derivados porfirínicos: síntese e avaliação de propriedades biológicas, 2013. Dissertação (Bioquímica) - Universidade de Aveiro (Co-orientador).

Participação editorial em revistas Magazine editorial participation

1.	Menezes, J. C. J. M. D. S.. Arabian Journal of Chemistry, desde 2014/07/10, Função ou tipo de participação: Reviewer, Editora: Production and Hosting by Elsevier B.V. on behalf of King Saud University.
2.	Menezes, J. C. J. M. D. S.. Molecules, desde 2013/08/01, Função ou tipo de participação: Reviewer, Editora: MDPI journal.
3.	Menezes, J. C. J. M. D. S.. Tetrahedron, desde 2013/08/01, Função ou tipo de participação: Reviewer, Editora: Elsevier.
4.	Menezes, J. C. J. M. D. S.. Combinatorial Chemistry and High Throughput Screening , desde 2013/08/01, Função ou tipo de participação: Reviewer, Editora: Bentham Science Publishers.
5.	Menezes, Jose Carlos Joaquim Maia De Souza. International Journal of Photoenergy, desde 2013/06/18, Função ou tipo de participação: Reviewer, Editora: Hindawi Publishing Corporation.
6.	Menezes, Jose Carlos Joaquim Maia De Souza. Journal of Mass Spectrometry, de 2013/05/17 até 2013/05/25, Função ou tipo de participação: Reviewer.
7.	Menezes, Jose Carlos Joaquim Maia De Souza. Journal of Heterocyclic Chemistry, de 2012/01/12 até 2013/02/04, Função ou tipo de participação: Reviewer, Editora: http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1943-5193.

Produção científica Scientific production

Produção técnica Technical production

Dados complementares data

Total

Produção científica Scientific production

18

Artigos científicos em revistas Papers in periodics

18

Com arbitragem científica With scientific refereeing

18

Total

Produção técnica Technical production

17

Outros tipos de produção técnica Other technical production

17

Total

Dados complementares (Additional data)

8

Orientações Orientations

1

Participação editorial em revistas Magazine editorial participation

7

Sónia Maria Gomes Pires