Biotin-conjugated tumour-targeting photocytotoxic iron(III) complexes

Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences

Volumn 371, Issue 1995, 2013, Pages

  Saha, Sounik ^a   Majumdar, Ritankar ^a   Hussain, Akhtar ^a   Dighe, Rajan R ^a   Chakravarty, Akhil R ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Cellular uptake; Dipyridophenazine biotin conjugates; Iron; Photocytotoxicity; Reactive oxygen species; Streptavidin binding

Indexed keywords

BINDING ENERGY; CELL CULTURE; DIMETHYL SULFOXIDE; INORGANIC COMPOUNDS; IRON; IRON COMPOUNDS; MOLECULAR BIOLOGY; OXYGEN; PROTEINS;

CELLULAR UPTAKE; DIPYRIDOPHENAZINE BIOTIN CONJUGATES; PHOTOCYTOTOXICITY; REACTIVE OXYGEN SPECIES; STREPTAVIDIN;

COENZYMES;

BIOTIN; IRON; PHOTOSENSITIZING AGENT; REACTIVE OXYGEN METABOLITE;

ARTICLE; CELL STRAIN HEPG2; CELLULAR UPTAKE; DIPYRIDOPHENAZINE BIOTIN CONJUGATES; EXPERIMENTAL NEOPLASM; HUMAN; LIGHT; METABOLISM; METHODOLOGY; PATHOLOGY; PHOTOCHEMOTHERAPY; PHOTOCYTOTOXICITY; STREPTAVIDIN BINDING; SYNTHESIS; TREATMENT OUTCOME;

CELLULAR UPTAKE; DIPYRIDOPHENAZINE BIOTIN CONJUGATES; IRON; PHOTOCYTOTOXICITY; REACTIVE OXYGEN SPECIES; STREPTAVIDIN BINDING;

BIOTIN; HEP G2 CELLS; HUMANS; IRON; LIGHT; NEOPLASMS, EXPERIMENTAL; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; TREATMENT OUTCOME;

EID: 84887325778     PISSN: 1364503X     EISSN: None     Source Type: Journal    
DOI: 10.1098/rsta.2012.0190     Document Type: Article

References (53)

1. Ethirajan M, Chen Y, Joshi P, Pandey RK. 2011 The role of porphyrin chemistry in tumor imaging and photodynamic therapy. Chem. Soc. Rev. 40, 340-362. (doi:10.1039/B915149B)
2. Bonnett R. 2000 Chemical aspects of photodynamic therapy. London, UK: Gordon & Breach.
3. Ojima I et al. 2002 Tumor-specific novel taxoid-monoclonal antibody conjugates. J. Med. Chem. 45, 5620-5623. (doi:10.1021/jm025540g) (Pubitemid 35453753)
4. Ludwig JA, Weinstein JN. 2005 Biomarkers in cancer staging, prognosis and treatment selection. Nat. Rev. Cancer 5, 845-856. (doi:10.1038/nrc1739) (Pubitemid 41746029)
5. Jaracz S, Chen J, Kuznetsova LV, Ojima I. 2005 Recent advances in tumor-targeting anticancer drug conjugates. Bioorg. Med. Chem. 13, 5043-5045. (doi:10.1016/j.bmc.2005.04.084) (Pubitemid 41039965)
6. Ojima I. 2008 Guided molecular missiles for tumor-targeting chemotherapy-case studies using the second-generation taxoids as warheads. Acc. Chem. Res. 41, 108-119. (doi:10.1021/ar700093f)
7. Chen J, Jaracz S, Zhao X, Chen S, Ojima I. 2005 Antibody-cytotoxic agent conjugates for cancer therapy. Exp. Opin. Drug Deliv. 2, 873-890. (doi:10.1517/17425247.2.5.873) (Pubitemid 41488847)
8. Wu X, Ojima I. 2004 Tumor specific novel taxoid-monoclonal antibody conjugate. Curr. Med. Chem. 11, 429-435. (doi:10.2174/0929867043455963) (Pubitemid 38294347)
9. Hamaan PR et al. 2002 Gemtuzumab ozogamicin, a potent and selective Anti-CD33 antibodycalicheamicin conjugate for treatment of acute myeloid leukemia. Bioconjugate Chem. 13, 47-58. (doi:10.1021/bc010021y) (Pubitemid 34119634)
10. Bradley MO et al. 2001 Tumor targeting by covalent conjugation of a natural fatty acid to paclitaxel. Clin. Cancer Res. 7, 3229-3238. (Pubitemid 32963848)
11. Kuznetsova L, Chen J, Sun L, Wu X, Pepe A, Veith JM, Pera P, Bernacki RJ, Ojima I. 2006 Syntheses and evaluation of novel fatty acid-second-generation taxoid conjugates as promising anticancer agents. Bioorg. Med. Chem. Lett. 16, 974-977. (doi:10.1016/j.bmcl.2005. 10.089) (Pubitemid 43059863)
12. Leamon CP, Reddy JA. 2004 Folate-targeted chemotherapy. Adv. Drug Deliv. Rev. 56, 1127-1141. (doi:10.1016/j.addr.2004.01.008) (Pubitemid 38496512)
13. Lu Y, Low PS. 2002 Folate-mediated delivery of macromolecular anticancer therapeutic agents. Adv. Drug Deliv. Rev. 54, 675-693. (doi:10.1016/S0169- 409X(02)00042-X) (Pubitemid 35247522)
14. Lee JW, Lu JY, Low PS, Fuchs PL. 2002 Synthesis and evaluation of taxol-folic acid conjugates as targeted antineoplastics. Bioorg. Med. Chem. 10, 2397-2406. (doi:10.1016/S0968-0896(02) 00019-6)
15. Chu TC, Marks III JW, Lavery LA, Faulkner S, Rosenblum MG, Ellington AD, Levy M. 2006 Aptamer: toxin conjugates that specifically target prostate tumor cells. Cancer Res. 66, 5989-5992. (doi:10.1158/0008-5472)
16. Farokhzad OC, Cheng J, Teply BA, Sherifi I, Jon S, Kantoff PW, Richie JP, Langer R. 2006 Targeted nanoparticle-aptamer bioconjugates for cancer chemotherapy in vivo. Proc. Natl Acad. Sci. USA 103, 6315-6320. (doi:10.1073/pnas.0601755103)
17. Nakanishi T, Tamai I, Takaki A, Tsuji A. 2000 Cancer cell-targeted drug delivery utilizing oligopeptide transport activity. Int. J. Cancer 88, 274-280. (doi:10.1002/1097-0215(20001015)88: 23.0.CO;2-5)
18. Nagy A et al. 1998 Synthesis and biological evaluation of cytotoxic analogs of somatostatin containing doxorubicin or its intensely potent derivative,2-pyrrolinodoxorubicin. Proc. Natl Acad. Sci. USA 95, 1794-1799. (doi:10.1073/pnas.0610763104)
19. Luo Y, Bernshaw NJ, Lu Z-R, Kopecek J, Prestwich GD. 2002 Targeted delivery of doxorubicin by HPMA copolymer-hyaluronan bioconjugates. Pharm. Res. 19, 396-400. (doi:10.1023/A:1015170907274) (Pubitemid 34408935)
20. Russell-Jones G,McTavish K,McEwan J, Rice J, NowotnikD. 2004 Vitamin-mediated targeting as a potential mechanism to increase drug uptake by tumours. J. Inorg. Biochem. 98, 1625-1633. (doi:10.1016/j.jinorgbio.2004.07.009) (Pubitemid 39349188)
21. Reddy JA, Westrick E, Vlahov I, Howard SJ, Santhapuram HK, Leamon CP. 2006 Folate receptor specific anti-tumor activity of folate-mitomycin conjugates. Cancer Chemother. Pharmacol. 58, 229-236. (doi:10.1007/s00280-005- 0151-z)
22. Liu Z, Zhong Z, Peng G, Wang S, Du X, Yan D, Zhang Z, He Q, Liu J. 2009 Folate receptor mediated intracellular gene delivery using the charge changing solid lipid nanoparticles. Drug Deliv. 16, 341-347. (doi:10.1080/ 10717540903047387)
23. Leamon CP, Reddy JA, Vlahov IR, Vetzel M, Parker N, Nicoson JS, Xu L-C, Westrick E. 2005 Synthesis and biological evaluation of EC72: a new folate-targeted chemotherapeutic. Bioconjugate Chem. 16, 803-811. (doi:10.1021/bc049709b) (Pubitemid 41026166)
24. Chen S, Zhao X, Chen J, Chen J, Kuznetsova L, Wong SS, Ojima I. 2010 Mechanismbased tumor-targeting drug delivery system. Validation of efficient vitamin receptormediated endocytosis and drug release. Bioconjug. Chem. 21, 979-987. (doi:10.1021/bc9005656)
25. Saha S, Majumdar R, Roy M, Dighe RR, Chakravarty AR. 2009 An iron complex of dipyridophenazine as a potent photocytotoxic agent in visible light. Inorg. Chem. 48, 2652-2663. (doi:10.1021/ic8022612)
26. Saha S, Mallick D, Majumdar R, Roy M, Dighe RR, Chakravarty AR. 2011 Structure-activity relationship of photocytotoxic iron(III) complexes of modified dipyridophenazine ligands. Inorg. Chem. 50, 2975-2987. (doi:10.1021/ic1024229)
27. Perrin DD, Armarego WLF, Perrin DR. 1980 Purification of laboratory chemicals. Oxford, UK: Pergamon Press.
28. Wilson JG. 1990 Phenolic analogs of amino carboxylic acid ligands for 99mTc. N-(2-Hydroxybenzyl) glycines (hbg). Aust. J. Chem. 43, 1283-1289. (doi:10.1071/CH9901283)
29. Evans DF. 1959 The determination of the paramagnetic susceptibility of substances in solution by nuclear magnetic resonance. J. Chem. Soc. 2003-2005. (doi:10.1039/JR9590002003)
30. Evans DF, James TA. 1979 Variableerature magnetic-susceptibility measurements of spin equilibria for iron(III) dithiocarbamates in solution. J. Chem. Soc. Dalton Trans. 723-726. (doi:10.1039/DT9790000723)
31. Green NM. 1970 Spectrophotometric determination of avidin and biotin. Methods Enzymol. 18A, 418-424. (doi:10.1016/0076-6879(71)18342-5)
32. Reichman ME, Rice SA, Thomas CA, Doty P. 1954 A further examination of the molecular weight and size of desoxypentose nucleic acid. J. Am. Chem. Soc. 76, 3047-3053. (doi:10.1021/ja01640a067)
33. McGhee JD, von Hippel PH. 1974 Theoretical aspects of DNA-protein interactions: cooperative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. J. Mol. Biol. 86, 469-489. (doi:1016/0022-2836(74)90031-X)
34. Carter MT, Rodriguez M, Bard AJ. 1989 Voltammetric studies of the interaction of metal chelates with DNA. Tris-chelated complexes of cobalt(III) and iron(II) with 1,10-phenanthroline and 2,2-bipyridine. J. Am. Chem. Soc. 111, 8901-8911. (doi:10.1021/ja00206a020) (Pubitemid 20050086)
35. Freimoser FM, Jakob CA, Aebi M, Tuor U. 1999 The MTT [3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay is a fast and reliable method for colorimetric determination of fungal cell densities. Appl. Environ. Microbiol. 65, 3727-3729. (Pubitemid 29399011)
36. Iinuma S, Farshi SS, Ortel B, Hasan T. 1994 A mechanistic study of cellular photodestruction with 5-aminolaevulinic acid-induced porphyrin. Br. J. Cancer, 70, 21-28. (doi:10.1038/bjc.1994.244) (Pubitemid 24203623)
37. Le Bel CP, Ischiropoulos H, Bondy SC. 1992 Evaluation of the probe 2-,7-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress. Chem. Res. Toxicol. 5, 227-231. (doi:10.1021/tx00026a012)
38. Slim M, Durisic N, Grutter P, Sleiman HF. 2007 DNA-protein noncovalent cross-linking: ruthenium dipyridophenazine biotin complex for the assembly of proteins and gold nanoparticles on DNA templates. ChemBioChem 8, 804-812. (doi:10.1002/cbic.200600550) (Pubitemid 47183637)
39. Lo KK-W, Chung C-K, Zhu N. 2006 Nucleic acid intercalators and avidin probes derived from luminescent cyclometalated iridium(III)-dipyridoquinoxaline and-dipyridophenazine complexes. Chem. Eur. J. 12, 1500-1512. (doi:10.1002/chem.200500885) (Pubitemid 43200400)
40. Lu Y-H, Tang C, Wang W, Xi T. 2009 Down regulation of surviving gene and upregulation of p53 gene expression by siRNA induces apoptosis in human hepatocellular carcinoma cell line HepG2. J. Biomed. Sci. Eng. 2, 57-62. (doi:10.4236/jbise.2009.21010)
41. Ramaiah D, Eckert I, Arun KT, Weidenfeller L, Epe B. 2002 Squaraine dyes for photodynamic therapy: study of their cytotoxicity and genotoxicity in bacteria and mammalian cells. Photochem. Photobiol. 76, 672-677. (doi:10.1562/0031-8655(2002)0762.0.CO;2)
42. Yang X-L, Kaenzig C, Lee M, Wang AH-J. 1999 Binding of AR-1-144, a tri-imidazole DNA minor groove binder, to CCGG sequence analyzed by NMR spectroscopy. Eur. J. Biochem. 263, 646-651. (doi:10.1046/j.1432-1327.1999. 00515.x) (Pubitemid 29361936)
43. Waring MJ. 1965 Complex formation between ethidium bromide and nucleic acids. J. Mol. Biol. 13, 269-282. (doi:10.1016/S0022-2836(65)80096-1)
44. LePecq J-B, Paoletti C. 1967 A fluorescent complex between ethidium bromide and nucleic acids. J. Mol. Biol. 27, 87-106. (doi:10.1016/0022-2836(67) 90353-1)
45. An Y, Liu S-D, Deng S-Y, Ji L-N, Mao Z-W. 2006 Cleavage of double-strand DNA by linear and triangular trinuclear copper complexes. J. Inorg. Biochem. 100, 1586-1593. (doi:10.1016/j.jinorgbio.2006.05.002) (Pubitemid 44332521)
46. Hilz H,Wiegers U, Adamietz P. 1975 Stimulation of proteinase K action by denaturing agents: application to the isolation of nucleic acids and the degradation of 'masked' proteins. Eur. J. Biochem. 56, 103-108. (doi:10.1111/j.1432-1033.1975.tb02211.x)
47. Law B, Tung C-H. 2009 Proteolysis: a biological process adapted in drug delivery, therapy, and imaging. Bioconjugate Chem. 20, 1683-1695. (doi:10.1021/bc800500a)
48. Kratz F, Müller IA, Ryppa C, Warnecke A. 2008 Prodrug strategies in anticancer chemotherapy. ChemMedChem 3, 20-53. (doi:10.1002/cmdc.200700159)
49. Wu W et al. 2006 Targeting cell-impermeable prodrug activation to tumor microenvironment eradicates multiple drug-resistant neoplasms. Cancer Res. 66, 970-980. (doi:10.1158/0008-5472) (Pubitemid 43165965)
50. Pacheco-Alvarez D, Solorzano-Vargas RS, Gonzalez-Noriega A, Michalak C, Zempleni J, Leon-Del-Rio A. 2005 Biotin availability regulates expression of the sodium-dependent multivitamin transporter and the rate of biotin uptake in HepG2 cells. Mol. Genet. Metab. 85, 301-307. (doi:10.1016/j.ymgme.2005.04.001) (Pubitemid 41074114)
51. Mahato R, Tai W, Cheng K. 2011 Prodrugs for improving tumor targetability and efficiency. Adv. Drug. Deliv. Rev. 63, 659-670. (doi:10.1016/j.addr.2011. 02.002)
52. Luo S, Kansara V, Zhu X, Mandava NK, Pal D, Mitra AK. 2006 Functional characterization of sodium-dependent multivitamin transporter in MDCK-MDR1 cells and its utilization as a target for drug delivery. Mol. Pharm. 3, 329-339. (doi:10.1021/mp0500768) (Pubitemid 44021439)
53. Kansara V, Luo S, Balasubrahmanyam B, Pal D, Mitra AK. 2006 Biotin uptake and cellular translocation in human derived retinoblastoma cell line (Y-79): a role of hSMVT system. Int. J. Pharm. 312, 43-52. (doi:10.1016/j.ijpharm.2005.12. 045)