Life cycle and description of the immature stages of a terrestrial firefly endemic to Mexico: Photinusextensus Gorham (Coleoptera, Lampyridae).

The life cycle, morphology, and bionomy of Photinusextensus Gorham, 1881, an endemic species of Mexico, are described. Redescriptions of adults (male and female) are also presented. Larvae were reared to the adult stage from eggs laid by females collected at the El Pedregal de San Ángel Ecological Reserve, south of Mexico City. The activity period of adults of P.extensus begins at the end of July and finishes by the end of August. Females lay between 3 and 198 eggs. Larvae hatch from the eggs after a period of 11 to 71 days, undergo 6 larval instars and a pupal stage in an annual cycle. Morphological characters of the sixth larval instar of P.extensus are compared with those of several other genera assigned to the tribe Photinini. Knowledge of the natural history of firefly larvae is relevant since most species do not feed as adults and therefore depend on resources acquired during the larval stage.

Synthetic approaches to multifunctional indenes.

The synthesis of multifunctional indenes with at least two different functional groups has not yet been extensively explored. Among the plausible synthetic routes to 3,5-disubstituted indenes bearing two different functional groups, such as the [3-(aminoethyl)inden-5-yl)]amines, a reasonable pathway involves the (5-nitro-3-indenyl)acetamides as key intermediates. Although several multistep synthetic approaches can be applied to obtain these advanced intermediates, we describe herein their preparation by an aldol-type reaction between 5-nitroindan-1-ones and the lithium salt of N,N-disubstituted acetamides, followed immediately by dehydration with acid. This classical condensation process, which is neither simple nor trivial despite its apparent directness, permits an efficient entry to a variety of indene-based molecular modules, which could be adapted to a range of functionalized indanones.

Indene-based frameworks targeting the 5-HT6 serotonin receptor: ring constraint in indenylsulfonamides using cyclic amines and structurally abbreviated counterparts.

Further studies in quest of 5-HT(6) serotonin receptor ligands led to the design and synthesis of a few selected examples of N-(inden-5-yl)sulfonamides with a ring-constrained aminoethyl side chain at the indene 3-position, some of which exhibited a high binding affinity, such as the pyrrolidine analogue 28 (K(i)=3nM). Moreover, the structurally abbreviated N-(inden-5-yl)sulfonamides showed K(i) values > or = 43 nM, which indicates that neither the N,N-aminoethyl nor the conformationally restricted aminoethyl side arm at the indene 3-position are required for binding. Selected compounds were then tested in a functional cAMP stimulation assay and found to act as 5-HT(6) antagonists, although with moderate potency at the micromolar level.

A new reticulated beetle (Coleoptera: Cupedidae) from Mexico with a catalogue of Cupedidae species of the world.

Paracupes mexicanus sp. nov., from Chiapas, Mexico, is described and illustrated. The subgenus Paracupoides Kirejtshuk et al., 2016 is synonymized under Paracupes Kolbe, 1898. Also, Rhipsideigma is synonymized with Cupes, resulting in new combinations: Cupes adjuncta (Neboiss) and Cupes anosibense (Neboiss), and restored combinations: Cupes cretaceotincta Kolbe, Cupes lugubris Fairmaire and Cupes raffrayi Fairmaire. Also, Cupes leucophaea Newman is reinstated from synonymy of Tenomerga leucophaea. In addition, a catalogue of the Cupedidae species of the world is presented.

A checklist of the Coleoptera (Insecta) from Morelos, Mexico.

Data from the literature and from specimens preserved at the Colección Nacional de Insectos (CNIN) Instituto de Biología, UNAM were used to compile a checklist of the fauna of Coleoptera of the state of Morelos, México. A sum of 70 families, 167 subfamilies, 361 tribes, 1,022 genera, and 2,606 species are recorded; from this 24 species are new records for Morelos. The State of Morelos ranks fourth in Coleoptera species richness for Mexico, following Veracruz (3,176 spp.), Oaxaca (2,148 spp.) and Chiapas (1,734 spp.). The checklist presented here provides a summary that can serve as a basis for future progress in the knowledge of Mexican Coleoptera.

Indene-based scaffolds. Design and synthesis of novel serotonin 5-HT6 receptor ligands.

A series of novel indene derivatives designed by a scaffold selection gave access to several examples of (Z)-arylmethylideneindenes and indenylsulfonamides that acted as serotonin 5-HT(6) receptor ligands. Different synthetic multistep routes could be applied to these target compounds, each with their own complexity and limitations. A reasonable route involved the (3-indenyl)acetic acids as the key intermediates, and two alternatives were also examined. The first protocol used was a two-step sequence employing a modified Horner-Wadsworth-Emmons reaction, but better results were obtained with a procedure based on the condensation of indanones with the lithium salt of ethyl acetate, followed immediately by dehydration with acid and hydrolysis/isomerization under basic catalysis. (3-Indenyl)acetic acids were transformed to the corresponding acetamides, which were effectively reduced to indenylsulfonamides using an optimized procedure with AlH(3)-NMe(2)Et. The binding at the 5-HT(6) receptor was with moderate affinity (K(i) = 216.5 nM) for the (Z)-benzylideneindenylsulfonamide and enhanced affinity for the simple indenylsulfonamide counterpart (K(i) = 50.6 nM). Selected indenylsulfonamides were then tested, showing K(i) values as low as 20.2 nM.

Comparative morphology of the spermatheca in Megalopodidae (Coleoptera, Chrysomeloidea).

The spermatheca is an organ that stores and maintains viability of sperm until fertilization. It has an important role in copulation and oviposition, and it is highly informative in species delimitation. Here, we present a comparative study of the spermathecal morphology in the coleopteran family Megalopodidae. The spermathecae of 34 species, representing 13 genera and all three subfamilies, were studied. Illustrations are newly provided for all species, except in 14 cases in which illustrations were reproduced from previously published literature. Our results show that each subfamily of Megalopodidae can be effectively differentiated based on the particular spermathecal anatomy. In addition, the spermathecal anatomy presents a range of variation within each subfamily, useful for diagnosing species and, in some cases, identifying groups of genera. For instance, the "American group" is thus recognized in this study.

Revision of Ogdoecosta Spaeth 1909 with description of Ogdoecosta paraflavomaculata López-Pérez, sp. nov. (Coleoptera: Chrysomelidae: Cassidinae: Mesomphaliini).

The tortoise beetle genus Ogdoecosta Spaeth 1909 is revised and an illustrated key to 12 species is provided, based on a morphological analysis of all species. All the known species are redescribed and one new species, Ogdoecosta paraflavomaculata López-Pérez sp. nov., is described from Belize and México. Lectotypes are designated for O. omissa Dohrn 1880, O. epilachnoides (Champion 1893), O. fasciata (Boheman 1856), O. flavomaculata (Champion 1893), O. mexicana (Champion 1893 and O. obliterata (Champion 1893). The distribution ranges for O. biannularis (Boheman 1854), O. catenulata (Boheman 1854), O. decemstillata (Boheman 1856), O. epilachnoides, O. fasciata, O. guttifera, O. juvenca, and O. obliterata are extended within México. Ogdoecosta guttifera (Boheman) is a new record for Venezuela.

Resequencing and assembly of seven complex loci to improve the Leishmania major (Friedlin strain) reference genome.

BACKGROUND: Leishmania parasites cause severe human diseases known as leishmaniasis. These eukaryotic microorganisms possess an atypical chromosomal architecture and the regulation of gene expression occurs almost exclusively at post-transcriptional levels. Accordingly, sequencing of the genome of Leishmania major, and subsequently the genome of other related species, was paramount for highlighting these peculiar molecular aspects. Recently, we carried out an analysis of gene expression by massive sequencing of RNA in the L. major promastigote, and data derived from that analysis were suggestive of possible errors in the current genome assembly for this Leishmania species. RESULTS: During the analysis by RNA-Seq of the transcriptome for L. major Friedlin strain, 163,714 reads could not be aligned with the reference genome. Thus, de novo assembly with these reads was carried out and the resulting contigs were further analyzed. After detailed homology searches using available databases, it was postulated that 15 contigs might correspond to genomic sequences lost during the initial genome assembly of the L. major Friedlin strain. This was experimentally confirmed by PCR amplification, cloning and sequencing of the new genomic regions. As a result, we have identified seven regions of the L. major (Friedlin) genome that were lost during the sequence assembly. This led to the uncovering of six new genes (LmjF.15.1475, LmjF.15.0285, LmjF.24.0765, LmjF.14.0860, LmjF.19.0305, and LmjF.27.2035), and correction of the annotation for two others (LmjF.15.1480 and LmjF.27.2030). Our data suggest that these genomic regions probably collapsed during the genome assembly due to the existence of gene duplications and/or repeated regions surrounding the missed genes. CONCLUSION: RNA-seq data helped to reconstruct some genomic regions misassembled during the L. major Friedlin genome assembly, which is otherwise quite robust. On the other hand, this study shows that data derived from massive sequencing approaches, including RNA-Seq, should be carefully inspected to improve current genome definition and gene annotations.

Indene-based scaffolds. 2. An indole-indene switch: discovery of novel indenylsulfonamides as 5-HT6 serotonin receptor agonists.

Scaffold selection involving an indole-to-indene core change led to the discovery of a series of indenylsulfonamides that act as 5-HT6 serotonin receptor agonists. The variety of the targeted ligands and their synthetic complexity required multistep synthetic approaches. The novel indenylsulfonamides exhibited variable binding affinities for the 5-HT6 receptor, and the in vitro primary binding profiles of the preferred compounds revealed them to be 5-HT6 receptor agonists with Ki values > or =4.5 nM. The structural changes responsible for enhancing the affinities indicated a directing effect modulated by the nature of the indene core, the substitution at the aminoethyl side chain, and especially by the aryl(heteroaryl)sulfonyl group on the indene 5-position. A representative of the family, the N-(inden-5-yl)imidazothiazole-5-sulfonamide (43), exhibited a high affinity and functioned as a potent full agonist for the 5-HT6 receptor (Ki = 4.5 nM, EC50 = 0.9 nM, Emax = 98%).

Identification of novel indanylsulfonamide guanylhydrazones as potent 5-HT6 serotonin receptor antagonists.

Changing the N,N-(dimethylamino)ethyl side chain in the N-[3-(aminoethyl)inden-5-yl]sulfonamide 5-HT(6) serotonin receptor agonists 1 by a conformationally rigid guanylhydrazone moiety at the indene 3-position led to the identification of the title indanylguanylhydrazones 6, which exhibited excellent binding affinities and an antagonistic response at the 5-HT(6) receptor, with K(i) and IC(50) values in the nanomolar range (K(i) >or= 1.2 nM, IC(50) >or= 47 nM, and I(max)