Skip to main content

Advertisement

SpringerLink
Log in

Assessment of acute toxicity and cytotoxicity of fluorescent markers produced by cardanol and glycerol, which are industrial waste, to different biological models

  • Research Article
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

The amphyphylic triazoanilines recently synthesized 1-(4-(3-aminophenyl)-1H-1,2,3- triazole-1-yl)-3-(3-pentadecylphenoxy)propan-2-ol (1) and 1-(4-(4-aminophenyl)-1H- 1,2,3-triazole-1-yl)-3-(3-pentadecylphenoxy)propan-2-ol (2), synthesized from cardanol and glycerol, have photophysical properties which allow their use in the development of fluorescent biomarkers with applicability in the biodiesel quality control. Based on this, the present research evaluated the toxic effects of both compounds in different biological models through the investigation of survival and mortality percentages as a measure of acute toxicity on Daphnia similis and Oreochromis niloticus, larvicidal assay against Aedes aegypti, and cytotoxic activity on mammary cells. Results demonstrate that these triazoanilines 1 and 2 have shown low acute toxicity to the biological models investigated in this study up to the following concentrations: 4.0 mg L-1 (D. similis), 4.0 mg L-1 (A. aegypti larvae), 1.0 mg L-1 (O. niloticus), and 1.0 mg mL-1 (mammary cells). This fact suggests the potential for safe use of compounds 1 and 2 as fluorescent markers for the monitoring of biodiesel quality, even in the case of environmental exposure. Besides all of that, the reuse of cardanol and glycerol, both industrial wastes, favors the maintenance of environmental health and is in agreement with the assumptions of green chemistry.

ᅟ

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  • ABNT - Associação Brasileira de Normas Técnicas (2004) NBR 12713: Ecotoxicologia aquática – Toxicidade aguda – Método de ensaio com Daphnia spp (Cladocera, Crustacea). 21 p

  • ABNT - Associação Brasileira de Normas Técnicas (2016) NBR 15088: Ecotoxicologia aquática - Toxicidade aguda - Método de ensaio com peixes (Cyprinidae). 25 p

  • Afifi M, Saddick S, Abu Zinada OA (2016) Toxicity of silver nanoparticles on the brain of Oreochromis niloticus and Tilapia zillii. Saudi J Biol Sci 23:754–760. https://doi.org/10.1016/j.sjbs.2016.06.008

    Article  CAS  Google Scholar 

  • Bhanu PV, Pankaj KK (2017) Monitoring petroleum fuel adulteration: a review of analytical methods. Trends Anal Chem 92:1–11. https://doi.org/10.3390/s18051551

    Article  CAS  Google Scholar 

  • Barnsley JE, Shillito GE, Larsen CB, Van der Salm H, Wang LE, Lucas NT, Gordon KC (2016) Benzo [c][1,2,5] thiadiazole donor−acceptor dyes: a synthetic, spectroscopic, and computational study. J Phys Chem A 120:1853–1866. https://doi.org/10.1021/acs.jpca.6b00447

    Article  CAS  Google Scholar 

  • Beatriz A, Araújo YJK, Lima DP (2011) Glicerol: um breve histórico e aplicação em sínteses estereosseletivas. Quim Nova 2:306–319. https://doi.org/10.1590/S0100-40422011000200025

    Article  Google Scholar 

  • Beatriz A, De Lima D, Souza AP, Galdino DT, Silva ECR, Ito FM, Gomes RS, Arruda EJ. Processo de produção e uso de misturas de surfactantes iônicos do líquido da casca da castanha do caju e do óleo de mamoma como larvicida (2015); Brasil. Patente: Privilégio de inovação. Número do registro: BR10201500723. Data de depósito: 16/03/2015. Instituição de registro: INPI – Instituto Nacional da Propriedade Industrial

  • Bendary E, Francis RR, Ali HMG, Sarwat MI, El Hady S (2013) Antioxidant and structure-activity relationships (SARs) of some phenolic and anilines compounds. Ann Agric Sci 58:173–181. https://doi.org/10.1016/j.aoas.2013.07.002

    Article  Google Scholar 

  • Bluhm K, Heger S, Seiler TB, Hallare AV, Schäffer A, Hollert H (2012) Toxicological and ecotoxicological potencies of biofuels used for the transport sector - a literature review. Energy Environ Sci 5:7381–7392. https://doi.org/10.1039/c2ee03033k

    Article  CAS  Google Scholar 

  • Braga FC, Prasad AN, da Silva Gomes R, do Nascimento VA, Oliveira SL, Caires ARL, de Lima DP, Beatriz A (2017) Design, synthesis and fluorescence analysis of potential fluorescent markers based on cardanol and glycerol. Dyes Pigments 141:235–244. https://doi.org/10.1016/j.dyepig.2017.02.032

    Article  CAS  Google Scholar 

  • Brazil (2005) Ministério do Meio Ambiente. Conselho Nacional do Meio Ambiente. Resolução n° 357, de 17 de março de 2005. Dispõe sobre a classificação dos corpos de água e diretrizes para o seu enquadramento, bem com estabelece as condições e padrões de lançamento de efluentes, e dá outras providências. Diário Oficial da União, Brasília, DF, 18 mar. 2005. Seção 1:58–63

    Google Scholar 

  • Campos-Garcia J, Martinez DST, Alves OL, Leonardo AFG, Barbieri E (2015) Ecotoxicological effects of carbofuran and oxidised multiwalled carbon nanotubes on the freshwater fish Nile tilapia: nanotubes enhance pesticide ecotoxicity. Ecotoxicol Environ Saf 111:131–137. https://doi.org/10.1016/j.ecoenv.2014.10.005

    Article  CAS  Google Scholar 

  • Carvalho GHF, Andrade MA, Araújo CN, Santos ML, Castro NA, Charneau S, Monnerat R, Santana JM, Bastos IMD (2019) Larvicidal and pupicidal activities of eco-friendly phenolic lipid products from Anacardium occidentale nutshell against arbovirus vectors. Environ Sci Pollut Res. https://doi.org/10.1007/s11356-018-3905-y

  • Durjava MK, Kolar B, Arnus L, Papa E, Kovarich S, Sahlin U, Peijnenburg W (2013) Experimental assessment of the environmental fate and effects of triazoles and benzotriazole. Atla 41:65–75

    CAS  Google Scholar 

  • Ezzedinne R, Banaw AA, Tovmasyan A, Craik JD, Haberle IB, Benov LT (2013) Effect of molecular characteristics on cellular uptake, subcellular localization,and phototoxicity of Zn (II) N-alkylpyridylporphyrins. J Biol Chem 288:36579–36588. https://doi.org/10.1074/jbc.M113.511642

    Article  CAS  Google Scholar 

  • Fabris C, Soncin M, Jori G, Habluetzel A, Lucantoni L, Sawadogo S, Guidolina L, Coppellottia O (2012) Effects of a new photoactivatable cationic porphyrin on ciliated protozoa and branchiopod crustaceans, potential components of freshwater ecosystems polluted by pathogenic agents and their vectors. Photochem Photobiol Sci 11:294–301. https://doi.org/10.1039/C1PP05154G

    Article  CAS  Google Scholar 

  • Fargione J, Hill J, Tilman D, Polasky S, Hawthorne P (2008) Land clearing and the bio-fuel carbon debt. Science 319:1235–1238. https://doi.org/10.1126/science.1152747

    Article  CAS  Google Scholar 

  • Figueira ACB, Oliveira KT, Serra OA (2011) New porphyrins tailored as biodiesel fluorescent markers. Dyes Pigments 91:383–388. https://doi.org/10.1016/j.dyepig.2011.05.020

    Article  CAS  Google Scholar 

  • Garaventa F, Gambardella C, Di Fino A, Pittore M, Faimali M (2010) Swimming speed alteration of Artemia sp. and Brachionus plicatilis as a sub-lethal behavioural end-point for ecotoxicological surveys. Ecotoxicology 19:512–519. https://doi.org/10.1007/s10646-010-0461-8

    Article  CAS  Google Scholar 

  • García JI, Garcia-Marin H, Pires E (2014) Glycerol based solvents: synthesis, properties and applications. Green Chem 16:1007–1033. https://doi.org/10.1039/C3GC41857J

    Article  Google Scholar 

  • Golovanov AA, Odin IS, Bekin VV, Vologzhanina AV, Bushmarinov IS, Zlotskiic SS, Gerasimov YL, Purygind PP (2016) Azolyl-substituted 1,2,3-Triazoles. Russ J Org Chem 52:414–420. https://doi.org/10.1134/S1070428016030209

    Article  CAS  Google Scholar 

  • Heger S, Miaomiao D, Bauer K, Schäffer A, Hollert H (2018) Comparative ecotoxicity of potencial biofuels to water flea (Daphnia magna), zebrafish (Danio rerio) and Chinese hamster (Cricetulus griseus) V79 cells. Sci Total Environ 631-632:216–222. https://doi.org/10.1016/j.scitotenv.2018.03.028

    Article  CAS  Google Scholar 

  • Horton N, Mathew P (2014) Novel use of proliferating cell nuclear antigen as a biomarker of metastatic Cancer Available from: https://digitalcommons.hsc.unt.edu/rad/RAD14/Cancer/14/

  • Kalligeros S, Zannikos F, Stournas S, Lois E (2003) Fuel adulteration issues in Greece. Energy 28:15–26. https://doi.org/10.1016/S0360-5442(02)00091-9

    Article  Google Scholar 

  • Kanyathare B, Peiponen KE (2018) Hand-held refractometer-based measurement and excess permittivity analysis method for detection of diesel oils adulterated by kerosene in field conditions. Sensors 18:1551. https://doi.org/10.3390/s18051551

    Article  CAS  Google Scholar 

  • Kos I, Rebouças JS, De Freitas-Silva G, Salvemini D, Vujaskovic Z (2009) Lipophilicity of potente porphyrin- based antioxidants:comparison of ortho and meta isomers of Mn (III) N-alkyl pyridyl porphyrins. Free Radic Biol Med 47:72–78. https://doi.org/10.1016/j.freeradbiomed.2009.04.002

    Article  CAS  Google Scholar 

  • Kozubek A, Tyman JHP (1999) Resorcinolic lipids the natural non-isoprenoid phenolic Amphiphiles and their biological activity. Chem Rev 99:1–25. https://doi.org/10.1021/cr970464o

    Article  CAS  Google Scholar 

  • Kozubek A (1995) Determination of octanol/water partition coefficients for long-chain homologs of Orcinol from cereal grains. Acta Biochim Pol 42:247–252. https://doi.org/10.1016/j.foodchem.2007.12.011

    Article  CAS  Google Scholar 

  • Kumar NP, Nekkanti S, Kumari SS, Sharma P, Shankaraiah N (2017) Design and synthesis of 1,2,3-triazolo-phenanthrene hybrids as cytotoxic agents. Bioorg Med Chem Letters 27:2369–2376. https://doi.org/10.1016/j.bmcl.2017.04.022

    Article  CAS  Google Scholar 

  • Lakomska I, Hoffmann K, Wojtczak A, Sitkowski J, Maj E, Wietrzyk J (2014) Cytotoxic malonate platinum (II) complexes with 1,2,4-triazolo[1,5-α] pyrimidine derivatives: structural characterization and mechanism of the suppression of tumor cell growth. J Inorg Biochem 141:188–197. https://doi.org/10.1016/j.jinorgbio.2014.08.005

    Article  CAS  Google Scholar 

  • Larsen PS, Madsen CV, Riisgård HU (2008) Effect of temperature and viscosity on swimming velocity of the copepod Acartia tonsa: brine shrimp Artemia salina and rotifer Brachionus plicatilis. AquatBiol 4:47–54. https://doi.org/10.3354/ab00093

    Article  Google Scholar 

  • Lee HL, Er HM, Radhakrishnan AK (2009) In vitro anti-proliferative and antioxidante activities of stem extracts of pereskia bleo (Kunth) DC (Cactaceae). Malaysian J Sci 28:225–239. https://doi.org/10.22452/mjs.vol28no3.1

    Article  CAS  Google Scholar 

  • Li X, Lin Y, Yuan Y, Liu K, Qian X (2011) Novel efficient anticancer agents and DNA-intercalators of 1,2,3-triazol-1,8-naphthalimides: design, synthesis, and biological activity. Tetrahedron 67:2299–2304. https://doi.org/10.1016/j.tet.2011.01.063

    Article  CAS  Google Scholar 

  • Libralato G, Prato E, Migliore L, Cicero AM, Manfra L (2016) A review of toxicity testing protocols and endpoints with Artemia spp. Ecol Indic 69:35–49. https://doi.org/10.1016/j.ecolind.2016.04.017

    Article  CAS  Google Scholar 

  • Linsinger T, Koomen G, Emteborg H, Roebben G, Kramer G, Lamberty A (2004) Validation of the European Union’s reference method for the determination of solvent yellow 124 in gas oil and kerosene. Energy Fuel 18:1851–1854 b) Krutak JJ, Cushaman MR, Waever MA. US Patent No 5525516, 1996 c) Friswell MR. US Patent No. 5156653, 1992. https://doi.org/10.1021/ef049820d

  • Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65(1–2):55–63

    Article  CAS  Google Scholar 

  • OECD. OECD 203 fish acute toxicity test. OECD guidelines for the testing of chemicals, Section 2, 1992:10

  • OECD. OECD 202 Daphnia sp. Acute immobilisation test. OECD guidelines for the testing of chemicals, Section 6, 2004

  • Ordoudi SA, Tsimidou MZ, Vafiadis AP, BakalBassis EG (2006) Structure-DPPH. Scavenging activity relationships: parallel study of catechol and guaiacol acid derivatives. J Agric Food Chem 54:5763–5768. https://doi.org/10.1021/jf060132x

    Article  CAS  Google Scholar 

  • Pang YP, Brimijoin S, Ragsdale DW, Zhu KY, Suranyi R (2012) Novel and viable acetylcholinesterase target site for developing effective and environmentally safe insecticides. Curr Drug Targets 13:471–482

    Article  CAS  Google Scholar 

  • Perales E, García JI, Pires E, Aldea L, Lomba L, Giner B (2017) Ecotoxicity and QSAR studies of glycerol ethers in Daphnia magna. Chemosphere 183:277–285. https://doi.org/10.1016/j.chemosphere.2017.05.107

    Article  CAS  Google Scholar 

  • Pimentel MF, Pires D, Lima D, Martins LR, Beatriz A, Santaella ST et al (2009) Ecotoxicological analysis of cashew nut industry effluents, specifically two of its major phenolic components, cardol and cardanol. Pan-Am J Aquat Sci 4:363–368

    Google Scholar 

  • Puangmalee S, Petsom A, Thamyongkit PA (2009) Porphyrin derivative from cardanol as a diesel fluorescent marker. Dyes Pigments 82:26–30. https://doi.org/10.1016/j.dyepig.2008.10.015

    Article  CAS  Google Scholar 

  • Schweich LDC, Oliveira EJTD, Pesarini JR, Hermeto LC, Camassola M, Nardi NB et al (2017) All-trans retinoic acid induces mitochondria-mediated apoptosis of human adipose-derived stem cells and affects the balance of the adipogenic differentiation. Biomed Pharmacother 96:1267–1274. https://doi.org/10.1007/s11356-017-8662-9

    Article  CAS  Google Scholar 

  • Shemesh A, Kundu K, Peleg R, Yossef R, Kaplanov I, Ghosh S, Khrapunsky Y, Gershoni-Yahalom O, Rabinski T, Cerwenka A, Atlas R, Porgador A (2018) NKp44-derived peptide binds proliferating cell nuclear antigen and mediates tumor cell death. Front Immunol 9(1114). https://doi.org/10.3389/fimmu.2018.01114

  • Stasiuk M, Kozubek A (2010) “Biological activity of phenolic lipids”, Birkhäuser Verlag, Based/Switzerland Cell Mol Life Sci 67:841–860. https://doi.org/10.1007/s00018-009-0193-1

  • Su N-N, Xiong LX, Yu SJ, Zhang X, Cui C, Li ZM, Zhao WG (2013) Larvicidal activity and click synthesis of 2-Alkoxyl-2-(1,2,3-Triazole-1-yl) acetamide library. Comb Chem High Throughput Screen 16:484–493. https://doi.org/10.2174/1386207311316060009

    Article  CAS  Google Scholar 

  • Tyman JHP (2001) The chemistry and biochemistry of anarcardic acids. Recent research in lipids. Transworld Res 5:125–145

    CAS  Google Scholar 

  • Vani JM, Monreal MTFD, Auharek SA, Cunha-Laura AL, de Arruda EJ, Lima AR, da Silva CM, Antoniolli-Silva ACMB, de Lima DP, Beatriz A, Oliveira RJ (2018) The mixture of cashew nut shell liquid and castor oil results in an efficient larvicide against Aedes aegypti that does not alter embryo-fetal development, reproductive performance or DNA integrity. PLoS One 13(3):e0193509. https://doi.org/10.1371/journal.pone.0193509

    Article  CAS  Google Scholar 

Download references

Funding

This study was sponsored by Fundação de Apoio ao Desenvolvimento do Ensino, Ciência e Tecnologia do Estado de Mato Grosso do Sul – FUNDECT, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior – Brasil (CAPES) – Finance code 001, and Conselho Nacional de Desenvolvimento Científico e Tecnológico – CNPq.

Author information

Authors and Affiliations

  1. Stem Cell, Cell Therapy and Toxicological Genetics Research Centre (CeTroGen), “Maria Aparecida Pedrossian” University Hospital, Brazilian Hospital Services Company (EBSERH), Campo Grande, Mato Grosso do Sul, Brazil

    Bruno Ivo Pelizaro, Lucas Roberto Pessatto, Edwin José Torres Oliveira, Andréia Conceição Milan Brochado Antoniolli-Silva & Rodrigo Juliano Oliveira

  2. Master’s Program in Pharmacy, Faculty of Pharmaceutical Sciences, Food and Nutrition – FACFAN, Federal University of Mato Grosso do Sul, Campo Grande, Mato Grosso do Sul, Brazil

    Bruno Ivo Pelizaro & Jeandre Augusto dos Santos Jaques

  3. Chemistry Institute – INQUI, SINTMOL Laboratory, Federal University of Mato Grosso do Sul, Avenue Senador Filinto Müller, 1555 - Universitário, Campo Grande, Mato Grosso do Sul, 79074-460, Brazil

    Felipe Camargo Braga, Dênis Pires de Lima & Adilson Beatriz

  4. Laboratory of Ecotoxicology and Genotoxicity (LECOGEN), Faculty of Biological and Environmental Sciences – FCBA, Federal University of Grande Dourados, Dourados, Mato Grosso do Sul, Brazil

    Bruno do Amaral Crispim & Alexeia Barufatti Grisolia

  5. Laboratory of Environmental Quality, Faculty of Engineering Architecture and Urbanism and Geography – FAENG, Federal University of Mato Grosso do Sul, Campo Grande, Mato Grosso do Sul, Brazil

    Luiz Guilherme Maiolino Lacerda de Barros

  6. Graduate Programme in Genetics and Molecular Biology, Department of General Biology, State University of Londrina (UEL), Londrina, Paraná, Brazil

    Lucas Roberto Pessatto, Edwin José Torres Oliveira & Rodrigo Juliano Oliveira

  7. Graduate Programme in Health and Development in the Central-West Region, School of Medicine (FAMED) “Dr. Hélio Mandetta”, Federal University of Mato Grosso do Sul (UFMS), Cidade Universitária, S/N., Campo Grande, MS, 79070-900, Brazil

    Juliana Miron Vani, Andréia Conceição Milan Brochado Antoniolli-Silva & Rodrigo Juliano Oliveira

  8. Biosciences Institute- INBIO, Federal University of Mato Grosso do Sul, Campo Grande, Mato Grosso do Sul, Brazil

    Antonio Pancrácio de Souza

Authors
  1. Bruno Ivo Pelizaro
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Felipe Camargo Braga
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bruno do Amaral Crispim
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Luiz Guilherme Maiolino Lacerda de Barros
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Lucas Roberto Pessatto
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Edwin José Torres Oliveira
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Juliana Miron Vani
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Antonio Pancrácio de Souza
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Alexeia Barufatti Grisolia
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Andréia Conceição Milan Brochado Antoniolli-Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Dênis Pires de Lima
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. Jeandre Augusto dos Santos Jaques
    View author publications

    You can also search for this author in PubMed Google Scholar

  13. Adilson Beatriz
    View author publications

    You can also search for this author in PubMed Google Scholar

  14. Rodrigo Juliano Oliveira
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Adilson Beatriz or Rodrigo Juliano Oliveira.

Ethics declarations

All procedures and protocols followed approved guidelines for the ethical treatment of vertebrate animals, according to the Ethics Committee in Animals Experimentation from the Federal University of Grande Dourados under protocol # 09/2017-2.

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Responsible editor: Philippe Garrigues

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pelizaro, B.I., Braga, F.C., Crispim, B.d.A. et al. Assessment of acute toxicity and cytotoxicity of fluorescent markers produced by cardanol and glycerol, which are industrial waste, to different biological models. Environ Sci Pollut Res 26, 9193–9202 (2019). https://doi.org/10.1007/s11356-019-04376-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-019-04376-y

Keywords

Search

Navigation