In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas

Cazzamalli S, Figueras Agustí E, Petho L, Borbély AN, Steinkuhler C, Neri D, Sewald N (2018)
ACS OMEGA 3(11): 14726-14731.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Traditional chemotherapeutics used in cancer therapy do not preferentially accumulate in tumor tissues. The conjugation to delivery vehicles like antibodies or small molecules has been proposed as a strategy to increase the tumor uptake and improve the therapeutic window of these drugs. Here, we report the synthesis and the biological evaluation of a novel small molecule-drug conjugate (SMDC) comprising a high-affinity bidentate acetazolamide derivative, targeting carbonic anhydrase IX (CAIX), and cryptophycin, a potent microtubule destabilizer. The biological activity of the novel SMDC was evaluated in vitro, measuring binding to the CAIX antigen by surface plasmon resonance and cytotoxicity against SKRC-52 cells. In vivo studies showed a delayed growth of tumors in nude mice bearing SKRC-52 renal cell carcinomas.
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Zeitschriftentitel
ACS OMEGA
Band
3
Ausgabe
11
Seite(n)
14726-14731
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PUB-ID

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Cazzamalli S, Figueras Agustí E, Petho L, et al. In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas. ACS OMEGA. 2018;3(11):14726-14731.
Cazzamalli, S., Figueras Agustí, E., Petho, L., Borbély, A. N., Steinkuhler, C., Neri, D., & Sewald, N. (2018). In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas. ACS OMEGA, 3(11), 14726-14731. doi:10.1021/acsomega.8b02350
Cazzamalli, S., Figueras Agustí, E., Petho, L., Borbély, A. N., Steinkuhler, C., Neri, D., and Sewald, N. (2018). In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas. ACS OMEGA 3, 14726-14731.
Cazzamalli, S., et al., 2018. In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas. ACS OMEGA, 3(11), p 14726-14731.
S. Cazzamalli, et al., “In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas”, ACS OMEGA, vol. 3, 2018, pp. 14726-14731.
Cazzamalli, S., Figueras Agustí, E., Petho, L., Borbély, A.N., Steinkuhler, C., Neri, D., Sewald, N.: In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas. ACS OMEGA. 3, 14726-14731 (2018).
Cazzamalli, Samuele, Figueras Agustí, Eduard, Petho, Lilla, Borbély, Adina Noémi, Steinkuhler, Christian, Neri, Dario, and Sewald, Norbert. “In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas”. ACS OMEGA 3.11 (2018): 14726-14731.

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Daten bereitgestellt von Europe PubMed Central.

Synthesis and Biological Evaluation of RGD⁻Cryptophycin Conjugates for Targeted Drug Delivery.
Borbély A, Figueras E, Martins A, Esposito S, Auciello G, Monteagudo E, Di Marco A, Summa V, Cordella P, Perego R, Kemker I, Frese M, Gallinari P, Steinkühler C, Sewald N., Pharmaceutics 11(4), 2019
PMID: 30939768

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Dal Corso A, Cazzamalli S, Gebleux R, Mattarella M, Neri D., Bioconjug. Chem. 28(7), 2017
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Cazzamalli S, Ziffels B, Widmayer F, Murer P, Pellegrini G, Pretto F, Wulhfard S, Neri D., Clin. Cancer Res. 24(15), 2018
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Cazzamalli S, Dal Corso A, Neri D., Mol. Cancer Ther. 15(12), 2016
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PMID: 28303026
Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis.
Nahrwold M, Weiß C, Bogner T, Mertink F, Conradi J, Sammet B, Palmisano R, Royo Gracia S, Preuße T, Sewald N., J. Med. Chem. 56(5), 2013
PMID: 23387527
Vascular permeability in a human tumor xenograft: molecular size dependence and cutoff size.
Yuan F, Dellian M, Fukumura D, Leunig M, Berk DA, Torchilin VP, Jain RK., Cancer Res. 55(17), 1995
PMID: 7641188
Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting.
Weiss C, Figueras E, Borbely AN, Sewald N., J. Pept. Sci. 23(7-8), 2017
PMID: 28661555
Efficient synthesis of cryptophycin-52 and novel para-alkoxymethyl unit A analogues.
Eissler S, Bogner T, Nahrwold M, Sewald N., Chemistry 15(42), 2009
PMID: 19760734
Molecular Basis of Valine-Citrulline-PABC Linker Instability in Site-Specific ADCs and Its Mitigation by Linker Design.
Dorywalska M, Dushin R, Moine L, Farias SE, Zhou D, Navaratnam T, Lui V, Hasa-Moreno A, Casas MG, Tran TT, Delaria K, Liu SH, Foletti D, O'Donnell CJ, Pons J, Shelton DL, Rajpal A, Strop P., Mol. Cancer Ther. 15(5), 2016
PMID: 26944918
Development of a Small Molecule Tubulysin B Conjugate for Treatment of Carbonic Anhydrase IX Receptor Expressing Cancers.
Marks IS, Gardeen SS, Kurdziel SJ, Nicolaou ST, Woods JE, Kularatne SA, Low PS., Mol. Pharm. 15(6), 2018
PMID: 29715036
Recent approaches for the synthesis of modified cryptophycins.
Weiss C, Sammet B, Sewald N., Nat Prod Rep 30(7), 2013
PMID: 23732943
Approaches for the synthesis of functionalized cryptophycins.
Sammet B, Bogner T, Nahrwold M, Weiss C, Sewald N., J. Org. Chem. 75(20), 2010
PMID: 20857920
Toward prediction of efficacy of chemotherapy: a proof of concept study in lung cancer patients using [¹¹C]docetaxel and positron emission tomography.
van der Veldt AA, Lubberink M, Mathijssen RH, Loos WJ, Herder GJ, Greuter HN, Comans EF, Rutten HB, Eriksson J, Windhorst AD, Hendrikse NH, Postmus PE, Smit EF, Lammertsma AA., Clin. Cancer Res. 19(15), 2013
PMID: 23620410
Dual-display of small molecules enables the discovery of ligand pairs and facilitates affinity maturation.
Wichert M, Krall N, Decurtins W, Franzini RM, Pretto F, Schneider P, Neri D, Scheuermann J., Nat Chem 7(3), 2015
PMID: 25698334
A multicenter phase II study of the cryptophycin analog LY355703 in patients with platinum-resistant ovarian cancer.
D'Agostino G, del Campo J, Mellado B, Izquierdo MA, Minarik T, Cirri L, Marini L, Perez-Gracia JL, Scambia G., Int. J. Gynecol. Cancer 16(1), 2006
PMID: 16445613
Ligand-Targeted Drug Delivery.
Srinivasarao M, Low PS., Chem. Rev. 117(19), 2017
PMID: 28898067
Synthesis and biological evaluation of EC20: a new folate-derived, (99m)Tc-based radiopharmaceutical.
Leamon CP, Parker MA, Vlahov IR, Xu LC, Reddy JA, Vetzel M, Douglas N., Bioconjug. Chem. 13(6), 2002
PMID: 12440854
Targeted drug delivery for cancer therapy: the other side of antibodies.
Firer MA, Gellerman G., J Hematol Oncol 5(), 2012
PMID: 23140144
Novel unit B cryptophycin analogues as payloads for targeted therapy.
Figueras E, Borbely A, Ismail M, Frese M, Sewald N., Beilstein J Org Chem 14(), 2018
PMID: 29977395
A small-molecule drug conjugate for the treatment of carbonic anhydrase IX expressing tumors.
Krall N, Pretto F, Decurtins W, Bernardes GJ, Supuran CT, Neri D., Angew. Chem. Int. Ed. Engl. 53(16), 2014
PMID: 24623670
Inhibition of carbonic anhydrase IX targets primary tumors, metastases, and cancer stem cells: Three for the price of one.
Supuran CT, Alterio V, Di Fiore A, D' Ambrosio K, Carta F, Monti SM, De Simone G., Med Res Rev 38(6), 2018
PMID: 29635752
Protease-Cleavable Linkers Modulate the Anticancer Activity of Noninternalizing Antibody-Drug Conjugates.
Dal Corso A, Cazzamalli S, Gebleux R, Mattarella M, Neri D., Bioconjug. Chem. 28(7), 2017
PMID: 28662334
99mTc-labeled small-molecule inhibitors of prostate-specific membrane antigen for molecular imaging of prostate cancer.
Hillier SM, Maresca KP, Lu G, Merkin RD, Marquis JC, Zimmerman CN, Eckelman WC, Joyal JL, Babich JW., J. Nucl. Med. 54(8), 2013
PMID: 23733925
A non-internalizing antibody-drug conjugate based on an anthracycline payload displays potent therapeutic activity in vivo.
Dal Corso A, Gebleux R, Murer P, Soltermann A, Neri D., J Control Release 264(), 2017
PMID: 28867376
The cryptophycins as potent payloads for antibody drug conjugates.
Verma VA, Pillow TH, DePalatis L, Li G, Phillips GL, Polson AG, Raab HE, Spencer S, Zheng B., Bioorg. Med. Chem. Lett. 25(4), 2015
PMID: 25613677
Curative properties of noninternalizing antibody-drug conjugates based on maytansinoids.
Perrino E, Steiner M, Krall N, Bernardes GJ, Pretto F, Casi G, Neri D., Cancer Res. 74(9), 2014
PMID: 24520075
Next generation antibody drugs: pursuit of the 'high-hanging fruit'.
Carter PJ, Lazar GA., Nat Rev Drug Discov 17(3), 2017
PMID: 29192287
Radiolabeled somatostatin receptor antagonists are preferable to agonists for in vivo peptide receptor targeting of tumors.
Ginj M, Zhang H, Waser B, Cescato R, Wild D, Wang X, Erchegyi J, Rivier J, Macke HR, Reubi JC., Proc. Natl. Acad. Sci. U.S.A. 103(44), 2006
PMID: 17056720
Biodistribution and radiation dosimetry of 11C-labelled docetaxel in cancer patients.
van der Veldt AA, Hendrikse NH, Smit EF, Mooijer MP, Rijnders AY, Gerritsen WR, van der Hoeven JJ, Windhorst AD, Lammertsma AA, Lubberink M., Eur. J. Nucl. Med. Mol. Imaging 37(10), 2010
PMID: 20508935
Cryptophycins-309, 249 and other cryptophycin analogs: preclinical efficacy studies with mouse and human tumors.
Liang J, Moore RE, Moher ED, Munroe JE, Al-awar RS, Hay DA, Varie DL, Zhang TY, Aikins JA, Martinelli MJ, Shih C, Ray JE, Gibson LL, Vasudevan V, Polin L, White K, Kushner J, Simpson C, Pugh S, Corbett TH., Invest New Drugs 23(3), 2005
PMID: 15868377
Targeting carbonic anhydrase IX with small organic ligands.
Wichert M, Krall N., Curr Opin Chem Biol 26(), 2015
PMID: 25721398
Tubulin Inhibitor-Based Antibody-Drug Conjugates for Cancer Therapy.
Chen H, Lin Z, Arnst KE, Miller DD, Li W., Molecules 22(8), 2017
PMID: 28763044
Enhanced Therapeutic Activity of Non-Internalizing Small-Molecule-Drug Conjugates Targeting Carbonic Anhydrase IX in Combination with Targeted Interleukin-2.
Cazzamalli S, Ziffels B, Widmayer F, Murer P, Pellegrini G, Pretto F, Wulhfard S, Neri D., Clin. Cancer Res. 24(15), 2018
PMID: 29691298
Acetazolamide Serves as Selective Delivery Vehicle for Dipeptide-Linked Drugs to Renal Cell Carcinoma.
Cazzamalli S, Dal Corso A, Neri D., Mol. Cancer Ther. 15(12), 2016
PMID: 27609641
Strategies and challenges for the next generation of antibody-drug conjugates.
Beck A, Goetsch L, Dumontet C, Corvaia N., Nat Rev Drug Discov 16(5), 2017
PMID: 28303026
Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis.
Nahrwold M, Weiß C, Bogner T, Mertink F, Conradi J, Sammet B, Palmisano R, Royo Gracia S, Preuße T, Sewald N., J. Med. Chem. 56(5), 2013
PMID: 23387527
Vascular permeability in a human tumor xenograft: molecular size dependence and cutoff size.
Yuan F, Dellian M, Fukumura D, Leunig M, Berk DA, Torchilin VP, Jain RK., Cancer Res. 55(17), 1995
PMID: 7641188
Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting.
Weiss C, Figueras E, Borbely AN, Sewald N., J. Pept. Sci. 23(7-8), 2017
PMID: 28661555
Efficient synthesis of cryptophycin-52 and novel para-alkoxymethyl unit A analogues.
Eissler S, Bogner T, Nahrwold M, Sewald N., Chemistry 15(42), 2009
PMID: 19760734
Molecular Basis of Valine-Citrulline-PABC Linker Instability in Site-Specific ADCs and Its Mitigation by Linker Design.
Dorywalska M, Dushin R, Moine L, Farias SE, Zhou D, Navaratnam T, Lui V, Hasa-Moreno A, Casas MG, Tran TT, Delaria K, Liu SH, Foletti D, O'Donnell CJ, Pons J, Shelton DL, Rajpal A, Strop P., Mol. Cancer Ther. 15(5), 2016
PMID: 26944918

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