Formulation, characterization, and antitumor properties of trans- and cis-citral in the 4T1 breast cancer xenograft mouse model

Pharmaceutical Research

Volumn 32, Issue 8, 2015, Pages 2548-2558

  Zeng, San ^a   Kapur, Arvinder ^b   Patankar, Manish S ^b   Xiong, May P ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

Author keywords

Breast cancer; Citral; Geranial; Micelle; Neral

Indexed keywords

CITRAL; ANTINEOPLASTIC AGENT; ENZYME INHIBITOR; MICELLE; TERPENE;

ACUTE TOXICITY; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER INHIBITION; CANCER MODEL; CANCER TISSUE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DEGRADATION; DRUG DOSE REDUCTION; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; ENCAPSULATION; FEMALE; FLOW CYTOMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC50; IN VITRO STUDY; MOUSE; MOUSE MODEL; NONHUMAN; PH; PRIORITY JOURNAL; SUSTAINED DRUG RELEASE; SUSTAINED RELEASE FORMULATION; TUMOR VOLUME; TUMOR XENOGRAFT; WESTERN BLOTTING; ANIMAL; BAGG ALBINO MOUSE; BREAST NEOPLASMS; CELL SURVIVAL; CHEMISTRY; DRUG SCREENING; HUMAN; MEDICINAL CHEMISTRY; MICELLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ANIMALS; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL SURVIVAL; CHEMISTRY, PHARMACEUTICAL; ENZYME INHIBITORS; FEMALE; HUMANS; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICE, INBRED BALB C; MICELLES; MONOTERPENES; STEREOISOMERISM; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84985021929     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-015-1643-0     Document Type: Article

References (30)

1. Maswal M, Dar AA. Inhibition of citral degradation in an acidic aqueous environment by polyoxyethylene alkylether surfactants. Food Chem. 2013;138(4):2356-64.
2. Kimura K, Nishimura H, Iwata I, Mizutani J. Deterioration mechanism of lemon flavor. 2. Formation of off-odor substances arising from citral. J Agric Food Chem. 1983;31:801-4.
3. Onawunmi GO. Evaluation of the antimicrobial activity of citral. Lett Appl Microbiol. 1989;9:105-8.
4. Korenblum E, de Vasconcelos Goulart FR, de Almeida Rodrigues I, Abreu F, Lins U, Alves PB, et al. Antimicrobial action and anticorrosion effect against sulfate reducing bacteria by lemongrass (Cymbopogon citratus) essential oil and its major component, the citral. AMB Express. 2013;3(1):44.
5. Machado M, Pires P, Dinis AM, Santos-Rosa M, Alves V, Salgueiro L, et al. Monoterpenic aldehydes as potential anti-Leishmania agents: activity of Cymbopogon citratus and citral on L. infantum, L. tropica and L. major. Exp Parasitol. 2012;130(3):223-31.
6. Khan MS, Malik A, Ahmad I. Anti-candidal activity of essential oils alone and in combination with amphotericin B or fluconazole against multi-drug resistant isolates of Candida albicans. Med Mycol. 2012;50(1):33-42.
7. Helal GA, Sarhan MM, Abu Shahla AN, Abou El-Khair EK. Antimicrobial activity of some essential oils against microorganisms deteriorating fruit juices. Mycobiology. 2006;34(4):219-29.
8. Dudai N, Weinstein Y, Krup M, Rabinski T, Ofir R. Citral is a new inducer of caspase-3 in tumor cell lines. PlantaMed. 2005;71(5):484-8.
9. Liu Y, Whelan RJ, Pattnaik BR, Ludwig K, Subudhi E, Rowland H, et al. Terpenoids fromZingiber officinale (Ginger) induce apoptosis in endometrial cancer cells through the activation of p53. PLoS One. 2012;7(12):e53178.
10. Liang CP, Wang M, Simon JE, Ho CT. Antioxidant activity of plant extracts on the inhibition of citral off-odor formation. Mol Nutr Food Res. 2004;48(4):308-17.
11. Yang X, Tian H, Ho CT, Huang Q. Inhibition of citral degradation by oil-in-water nanoemulsions combined with antioxidants. J Agric Food Chem. 2011;59(11):6113-9.
12. Djordjevic D, Cercaci L, Alamed J, McClements DJ, Decker EA. Chemical and physical stability of citral and limonene in sodium dodecyl sulfate-chitosan and gumarabic-stabilized oil-in-water emulsions. J Agric Food Chem. 2007;55(9):3585-91.
13. Park S, Hong C, Choi S. Citral degradation in micellar structures formed with polyoxyethylene-type surfactants. Food Chem. 2015;170:443-7.
14. Choi SJ, Decker EA, Henson L, Popplewell LM, McClements DJ. Inhibition of citral degradation in model beverage emulsions using micelles and reverse micelles. Food Chem. 2010;122:111-6.
15. Maeda H, Wu J, Sawa T, Matsumura Y, Hori K. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review. J Control Release. 2000;65(1-2):271-84.
16. Woodward SC, Brewer PS, Moatamed F, Schindler A, Pitt CG. The intracellular degradation of poly(epsilon-caprolactone). J Biomed Mater Res. 1985;19(4):437-44.
17. Kwon GS, Yokoyama M, Okano T, Sakurai Y, Kataoka K. Biodistribution of micelle-forming polymer-drug conjugates. Pharm Res. 1993;10(7):970-4.
18. Soo P, Luo L, Maysinger D, Eisenberg A. Incorporation and release of hydrophobic probes in biocompatible polycaprolactone-blockpoly(ethylene oxice) micelles: implications for drug delivery. Langmuir. 2002;18:9996-10004.
19. Park Y, Lee J, Chang Y, Jeong J, Chung J, Lee M, et al. Radioisotope carrying polyethylene oxide-caprolactone copolymer micelles for targetable bone imaging. Biomaterials. 2003;23: 873-9.
20. Liu J, Zeng F, Allen C. In vivo fate of unimers and micelles of a poly(ethylene glycol)-block-poly(caprolactone) copolymer in mice following intravenous administration. Eur J Pharm Biopharm. 2007;65(3):309-19.
21. Savic R, Azzam T, Eisenberg A, Maysinger D. Assessment of the integrity of poly(caprolactone)-b-poly(ethylene oxide) micelles under biological conditions: a fluorogenic-based approach. Langmuir. 2006;22(8):3570-8.
22. Tsuboi S, Ishii N, Sakai T, Tari I, Utaka M. Oxidation of alcohols with electrolytic manganese-dioxide - its application for the synthesis of insect pheromones. Bull Chem Soc Jpn. 1990;63(7):1888-93.
23. Zeng S, Xiong MP. Trilayer micelles for combination delivery of rapamycin and siRNA targeting Y-box binding protein-1 (siYB-1). Biomaterials. 2013;34(28):6882-92.
24. Forrest ML, Won CY, Malick AW, Kwon GS. In vitro release of the mTOR inhibitor rapamycin from poly(ethylene glycol)-bpoly(epsilon-caprolactone) micelles. J Control Release. 2006;110(2): 370-7.
25. Xiong MP, Forrest ML, Ton G, Zhao A, Davies NM, Kwon GS. Poly(aspartate-g-PEI800), a polyethylenimine analogue of low toxicity and high transfection efficiency for gene delivery. Biomaterials. 2007;28(32):4889-900.
26. Rosenberg B, Van Camp L, Grimley EB, Thomson AJ. The inhibition of growth or cell division in Escherichia coli by different ionic species of platinum(IV) complexes. J Biol Chem. 1967;242(6): 1347-52.
27. Cleare M, Hoeschele J. Studies on the antitumor activity of group VIII transition metal complexes. Part I. Platinum (II) complexes. Bioinorg Chem. 1973;2:187-210.
28. Mai S, Muster B, Bereiter-Hahn J, Jendrach M. Autophagy proteins LC3B, ATG5 and ATG12 participate in quality control after mitochondrial damage and influence lifespan. Autophagy. 2012;8(1):47-62.
29. White E. Deconvoluting the context-dependent role for autophagy in cancer. Nat Rev Cancer. 2012;12(6):401-10.
30. Parajuli P, Pisarev V, Sublet J, Steffel A, Varney M, Singh R, et al. Immunization with wild-type p53 gene sequences coadministered with Flt3 ligand induces an antigen-specific type 1T-cell response. Cancer Res. 2001;61(22):8227-34.