Sandra Cortez-Maya

Synthesis of 5-aryl-1,4-benzodiazepine derivatives attached in resorcinaren-PAMAM dendrimers and their anti-cancer activity.

A series of resorcinaren-PAMAM dendrimers with benzodiazepines in the periphery were synthesized and their anticancer properties studied. The synthesized dendrimers showed potential anticancer activities, which were enhanced in the presence of a chloro-substituent in the second ring of the 5-aryl-1,4-benzodiazepine. The dendrimers were characterized by IR, (1)H and (13)C NMR, UV-vis absorption, electrospray (ES) and/or MALDI-TOF mass spectrometries.

Synthesis of 2-Aminobenzophenone Derivatives and Their Anticancer Activity

Abstract A number of 2-aminobenzophenones have been synthesized by acylation of para-chloroaniline with different 2-, 3-, 4-chloro- or fluorobenzoyl chloride in solid state via the Friedel–Crafts reaction. Synthesized compounds were characterized by 1H and 13C NMR, Fourier transform–infrared, ultraviolet–visible spectroscopy, mass spectrometry, and elemental analysis. Evaluation of biological activity in vitro showed that the selected compounds 9, 10, and 13 have potential anticancer activity. The presence of one chlorine atom in the second aromatic ring of the benzophenone molecule makes it more active. GRAPHICAL ABSTRACT

High Fluorescent Porphyrin-PAMAM-Fluorene Dendrimers

Two new classes of dendrimers bearing 8 and 32 fluorene donor groups have been synthesized. The first and second generations of these porphyrin-PAMAM-fluorene dendrimers were characterized by 1H-NMR, 13C-NMR, FTIR, UV-vis spectroscopy, elemental analyses and MALDI-TOF mass spectrometry. The UV-vis spectra showed that the individual properties of donor and acceptor moieties were preserved, indicating that the new dendrimers could be used as photosynthetic antennae. Furthermore, for fluorescent spectroscopy, these dendrimers showed good energy transfer.

Double Molecular Antenna Pyrene - Bridge - Fullerene C60

C60 pyrene anthrylvinylene triads were synthesized with good yields by an O-alkylation reaction of pyrene an- thracene chloride derivatives and functionalized fullerene C60. The presence of lateral butoxy chains imparts good solubil- ity. The NMR data indicate the formation of only the trans isomers. After C60 cyclopropanation, the UV-Vis spectra show the pyrene electronic transition with an absorption band extending from 400 to 800 nm due to the combination of the  electronic transition of the antrylvinylene moiety and the C60 band, regardless the extension of the anthrylvinylene moiety. However, the emission is almost mirror-like with respect to the absorption bands of pyrene, suggesting that the HOMO and LUMO are more localized on this substituent. All the obtained compounds were characterized by 1 H and 13 C NMR,

Synthesis, Characterization, and Nanomedical Applications of Conjugates between Resorcinarene-Dendrimers and Ibuprofen

Ibuprofen has been reported to possess anticancer activity. In the present work, four ibuprofen conjugates of resorcinarene-Polyamidoamine PAMAM-dendrimers were synthesized with eight or 16 ibuprofen moieties. The ibuprofen was released from the dendrimers in a dependent manner. The drug-conjugated nanoresorcinarene-dendrimers showed higher cellular uptake than free ibuprofen. In vitro cytotoxicity studies were performed with free ibuprofen and with the synthesized conjugates in U251, PC-3, K-562, HCT-15, MCF-7, SKLU-1, and MDA U251 (human glioblastoma), PC-3 (human prostatic adenocarcinoma), K-562 (human chronic myelogenous leukemia cells), HCT-15 (human colorectal adenocarcinoma), MCF-7 (human mammary adenocarcinoma), SKLU-1 (human lung adenocarcinoma), and MDA-MB-231 (human mammary adenocarcinoma) cancer cell lines by different cytotoxicity assays. Ibuprofen conjugates of the first and second generations showed significant cytotoxic effects towards the human glioblastoma (U251) and human mammary adenocarcinoma (MCF-7, MDA) cell lines. Moreover, the ibuprofen conjugates improved cytotoxicity compared to free ibuprofen. Increased therapeutic efficacy was observed with specific ibuprofen conjugates of the second generation using low doses.

Water-soluble porphyrin-PAMAM-conjugates of melphalan and their anticancer activity

Abstract p-[bis(chloro-2-ethyl)amino]-L-phenylalanine (melphalan) is an approved anti-cancer agent with a broad spectrum of antitumor activity. However, it has some disadvantages, such as poor water-solubility followed by rapid elimination, which reduce the target specificity. To solve these problems, porphyrin- poly(amidoamine) or PAMAM-conjugates of melphalan were synthesized and characterized. The dendrimeric conjugates showed satisfactory water solubility. It was found that the size of the dendrimer played a crucial role in controlling the drug content and diameter of the melphalan-conjugates. The in vitro studies of cell cytotoxicity revealed that by employing the dendrimeric conjugation strategy and using the PAMAM dendritic arms as spacers, the conjugates had good anti-cancer activity and lower toxicity than free melphalan.

Anticancer Activity of Resorcinarene-PAMAM-Dendrimer Conjugates of Flutamide

METHODS The synthesis of conjugates of flutamide with resorcinarene-PAMAM-dendrimers as well as alkyl and ethyl phenyl chains in the lower part of the macrocycle as a nucleus and diethylenetriamines in the dendritic branches gives the opportunity to obtain conjugates in one step of synthesis with 16 and 64 flutamide moieties in the structure. RESULTS The in vitro anticancer studies showed that the conjugates of flutamide are more active than the free flutamide and the flutamide derivatives, thus diminishing the amount of flutamide used. The resorcinarenedendrimer- flutamide conjugates with a high drug payload improve the activity of the drug. CONCLUSION This is important in delivering a sufficient amount of flutamide and suggests that the dendrimer facilitates more of the drug being introduced into cells. It was also observed that the new conjugates are less toxic than the anti-androgens.

Design and Synthesis of a Multi Cu(II)-porphyrin Array

A new class of porphyrin array was synthesized. The Cu(II) porphyrin-PAMAM-Cu(II) porphyrin was obtained in good yields. The EPR studies showed that all porphyrins obtained have signals of a copper complex with planar geometry, and no variation in the tetrahedral distortion of the porphyrin ring was observed. The UV-vis and emission studies showed that the intensity of the signal increased due to the presence of 5 porphyrin moieties in the structure. In order to further characterize this molecule, thin films were prepared by using the thermal evaporation method. The morphology of the film showed a homogeneous structure while conductivity measurements exhibit a good conductive response.