, Reagents and materials 5-(4-Calboxyphenyl)-10,15,20-triphenylchlorin (TPC) and tetraphenylporphyrin (TPP) were purchased flom Frontier Scientific The Fmoc-Asp

H. Wang, 9-fluolenyl-methoxy-carbonyl (Frnoc)-amino acids were from Senn Chemicals International (Dielsdorl Switzerland) Thin-layer chromatography (TLC) was carried out on Merck silica gel 60 F254 plates) and developed with the appropriate solvents. The TLC spots were visualized eithel by UV light or by heating plates sprayed with a solution of phosphomolybdic acid (5%, ethanolic solution) Chromatograpl-ty column was carl, Merck Chimie S.A.S, 230400.

, For the attachrnent of each amino acid, double couplings (20 and 40 min, respectively) wele performed using a thleefold excess of N-Frnoc-arnino acid and activation reagents 2-(lH-benzotriazol-l-yl)-1,1,3,3-tetra- methyl-uroniurn tetrafluor-oboratc (TBTU) (3eq.), l-hydroxybenzotriazole (HOBt) (3 eq.) and N,N-diisopropylethylarnine (DIEA) (9 eq.) in dirnethylformamide (DMF) Monitoring of the reaction was performed by the 2,4,6-trinitrobenzenesulf- onic acid test. For the attachment of the photosensitizer, only one coupling step using 2-fold excess was applied. During the photosensitizer coupling stage and all the next steps, light exposure was minimized by sealing the reaction vessel in foil to lirnit the occurrence of unwanted side reactions. Before cleavage, the peptide-resin was washed extensively rvith dichloromethane and dried irt uctt'tttt. rH NMR spectra were recorded on BRUKER AVANCE spectrometcr at 300MHz. Mass spectla arralyses (MALDI-TOF) u'ere can'ied out on Auall'ses werc pet'forrnecl oll tl Brrrkel Reflex lV tirne-of-flight rnass spectromcter (Brukcr-Daltonic, Bt'emen, Germany) equipped with the SCOUT 384 probe ion sour-ce, as described previously llll' The system uses zr pulsecl nitrogen laser' (337 1rn, model VSL- 337ND) with enei'gy of 400 prJ/pulse. The analysis was perforrned in the positive mode with an accelcration voltagc of 20 kV ancl a reflector voltage of 23 kV, The detector signals wele amplified and transferred to the XACQ plogram on a SUN work station (Sun Micr:osysterrrs Inc. palo AIto, CA) Spectra were processed ',vith tl-re XMass 5.1 program (Biuker Daltonics). External calibration of MALDI rlass spectra wAS carried out using soclic ancl potassic distribution with a rnixture of pEG 600 ancl pEG 1000

. Svnthesis, 20-rriphenvlchl'orin-RGD (l ) ttn4 5-(4- car bo x y p h c n-t' | ) -I 0, I 5,2 0-t r i p hen1, I po r p hv r in-RG D ( I b )

, The syntl-resis was performed using the preloaded Fmoc-Asp(OtBu)-Wang (capacity, 0'79 nmoUg) on a 0.15 g scale. The side chains of arginine and aspar-tic acicl were, respectii'ely. protected by Pbïpentamethylchroma-6-sulfonyl) group, and tertio-bvtyl (r-Bu) The succcssive coupling of Fmoc-Glir-oH ( 106 rng) and

. Fmoc-arg, BIOH (5a mg), and 0' 18 mL of DIEA in 5 mL of DMF were achieved After tl-re final removal of the Fmoc group, the peptide-resin was rvashed rvith cH2cl2 (6x -5 mL) and then dried in uacuo overnight. A standard cleavage rvith a mixture of 0.75 g of crystalline phenol, 0.25 rnl-of 1,2-ethanedithiol, 0.5 mL of thioanisole, 0.5 rnl of cleionizecl H'O, atrd l0mL of trifluoroacetic acicl (TFA) for 1.5 h alÏorclecl the crude pepticle. rvhich was lyophilized. The compounds rvere purified by Rp-HpLC on a C1s sernipreparative column (250x l0mrn, Pbf)-OH (230 nrg) in the presence of TBTU (l l4 rng)vlv) TFA-water/acetonitrile gradient, rnonitored by both absorbance ar 415 nm on a SPD-l0A UV-r'isible detector) and fluoresceuce on a RF IOAXL fluorcscence detector (Shimaclzu). After removal of the solvents, tlre purilied compounds wele lyophilized ancl analyzed by 'H NMR and mass spcctloscopy

, 20-rriphent,lchlorin-RG D ( I ) 'H NMR (DMSO) ô: -1.5g, -1.52 (s,2H22 (m. 2H. f3Asp), 3. t2 (rn, 2H. ôArg). 4.00 (s, t H. aGlv). +. t0 1., l u, c,Asp), 4.14(s.4H, cH2-chlorir),4.32 (s, lH, cArg),7.23 (s. lH. NHe-Arg).7.9g is, lH, NH-Arg, 1.50 (rn,2H, yArg),2.30 (m, 2H. f3Alg), 2 1 8, pp.8-20

, 20-triphenl,lpoylthyrin-RGD ( I b ) 'H NMR (DMSO) r): -2.g1 (s,2H, NH-pyr-iole), l.5g (m.2H. yArg),2.30 (rn,2H, 0Arg), 2.22,2.24 (rn.2H, pAsp), 3.r21m, 2H, ôA'g),4.02 (s, 2H, aGly). 4.12 (s, IH. cAsp).4.28 (s, lH, crArg).7.22 (s, lH. NHe-Atg), g.05 (s. lH, NH-Arg)

, Synthcsis ol 5-(4-utrbo.rvplten-t'l)-10,15,20-tt'ipltcrt"t,lt'hloritr-ct,cloIRGD

, tri(p-rol1'l)-20-(p-carbesyphcnvl)thlorin sut'cinidyl aster In the dark under a nitr-ogen atmosphere, ly'-hydroxysuccinirnide (26.1 rng,0.23 nmol) and dicyclohexylcarbodiimide (DCC)'(46.8 mg,0.23 rnmol) were added to a solution of 5, Synthcsi, vol.510, issue.5, pp.15-20

, The mixture was stirred 4 h at room tempet'ature. The solvent was evaporated and the clude rnaterial was purified by column chrornatoglaphy using EIOH/CH:Clz: 4196 (vlv) as the eluent. The flactions were tested by TLC and the pure compound was isolated as a p, p.12

'. Nmr, DMSO): d -1.50, -1.65 (s,2H, NH-pl,rrole),2.99 (s,4H, CHù,4.17 (s,4H, pp.7-26

, 20- ( p-carboxyam in o ) -c'h lorin J -hexanoi c ac id In the dark under a nitrogen atmosphere, to a solution of 8l mg of Fmoc-Lys-OH, HCI (0.20 mmol) in a minimum of DMF were added N-hydroxysuccinirnide activated chlorin (152 rng,0.20 mrnol) and triethylarnine (0.20 mmol,28.3 pL) in l0 mL CH2CI2 After been stirred at ambient temperature for 24h, the solvent was evapofated and the crude material was purified by column chromatography using EtOH/CHrCl2: 5195 (v/r') as the eluent. The fractions wel'e tested by TLC and the pure compound rvas isolated as a purple solid (l52mg,75ol'). 'H NMR (DMSO): ô -1.58, -1.52 (s,2H, pp.2-4

, 85 rnmol/g) on a 0. I l5 g scale. The side chains of arginine ancl aspartic acid were, respectively , protected by Pbf and t-Bu groups. The successive coupling of Fmoc-Arg(Pbfl-OH (190 mg), Fmoc-Lys(CO-Chll)-OH (152 rng), Fmoc-(D)Phe-OH (ll4 rng) and Fmoc- Asp(OtBu)-OH (l2l mg) in the presence of TBTU The linear, The synthesis was perforrned using the preloaded H-Gly-2-chlorotrityl PS lesin BtOH (45 mg), and 0.15 rnlol DIEA were achieved. Alter the flnal removal of the Fmoc gloup, tlre peptide-resin was washed with CH"CI" (6x 5 mL) and then dried rn oac'ao overnisht

|. Tr, [vgpiution.s rr.rcrl DCC, dicyclohexylcarbodiimide; DIPCDI. diisopropylcarboc]iimicle: DIEA. N,N-diisopropylethylanrine ; DMAP. 4-dimethylanrinopyridine; DNIF. dinrelhylformanride; DMSO, dinrethylsulfoxide

D. , BS, tctal bovine serum; HOBt, lhydroxybenzotriazole ; HPLC, high-perfornrance liquid chromalography; HOSu, H-hydroxysuccinimidel HUVEC, hurrran urnbilical vein endothelial cells: IvlALDI-TOF. nratrix-assisted laser desorption ionisation tinre-of-flight; LD56, Iight doses yielding 50'2, growth inhibition: MTT, 3-(4,5-dirnethylthiazol-2-yl)-2.5-diphenyl tetrazolium bronride; NaHCOr, sodiunr hydro-eenocarbonate; NMM. N-nrethylnrorpholinel Pbf, pp.4-62

T. Trilluoroacetic-trifluoroethane, 20-triphenylchlorin; TPP. tetlaphenylporphylrn RGDIK peptide was cleaved front the resin without allèctin-e other pr.otectil_q groups rvith l0nil of a mixturc of acetic acicl, 2,2.2 trilluoroerhanc tTFEt ancl CH2Cl.ill/3) for I h at room temperature. The t'esin was rvashed with three (irnes with acetic acid a'cl then lyophilizcd' The head-to-tail cyclization rvas performed b.v slou,ly adding a solution of the linear peptide etcetate salt in 20 rnl-of CH-,C12 to a solution of 50%, l-propane-phosphonic acid cyclic anhydride (T3P) in EtOAc (3 rnl-), triethylarnine (3 rnl-), and DMAp (10 rng) in 400 rnL of CH2CI2 After stirring overnight. the reaction rnixture wers concentrated and purified by chronratography (MeOH/AcOEt, 10/g0) ro afford I l5 mg ol'the cSlori' co'pled to the protected cyclic peptide. A standar'<i cleavage rvith a mixture of 0.75 g of crl,stalli'e phenol, 0-25 mL of 1,2-ethanedithiol, 0.5 rnl-of thioanisole, 0.5 mL of deionized H2O ancl l0 nil-ol'trifluoroacctic acid (TFA) fbr 1.5 h afforded the crucle pepticle, w5ic5 wits lyophilized' The compound was purified by RP-HPLC on â Crs se,ni-preparative column (250 x l0 rnrn I'D.. Apollo, Alltech) using a 0 TFA-rvater/acetonitrile gradient, monitored by both absorbance at 41,5 nm on a SPD-l0A UV visible derector(shirnactzu) and fluorescence on a RF I0AXL fluorescence detector (Shirnaclzu) After removal of the solvents.2 was lyophilized ancl kept in the dlrk in aliquots at -20 .C. Chemical identities rvere establishecl by 'H NMR ancl matlix-assistecl laser desorption ionization-time-of-fliglrt MALDI-TOF nIASS spectrornetr-v, AS cJescribed previously f l6]. 'H NMR (DMSO) r): -r.5g, -r.53 (s,2H, NH-p1,rrole), r.20(Ln, ?H. ôL1's), r.12(m, 2H, yArg), l.-53, 1.i2 (m, 2H. FArg), I .55 ('r. 2H, ôLys), m. 2H, Il(n)Phe), 2.84.2.94 (rn, 2H, FAsp) (s, lH, NHe-Arg),7.65 (s, rH, NH-Arg), g.05 (s, lH, NH-Asp), g.0g (s, rH. (o)Plre-NH) NH-Lys) MS (MALDI-TOFMS) mf :. calculared 1245.-55, pp.2-7

, Pltotophvsical properties 2.4. l. Ab.sorption cmd .fluorescence Absorption spectra w'ere recorded on a Perkin-Elmer (Larnbda 2

U. Spectrophotometer, Fluorescence spectra were recorded o1 a SpEX Fluorolog- 2 spectrofluorimeter 1680 (Jobin Yvon Longiurneau. France) equipped rvith a thennostated cell cornpartn-lent

. Detcrnirtatio, \.t)gan quantunt t,ieltl (a(tot))

, tlre light was scparatcd in a SpEX 16g0, 0.22 ptni cloLrble Intltrochrol'uator. Thc cietection at 1270 nni n'as clorre tlrrough u pTI S/N l-56-5 nronochronlittor. ancl thc ettiissiott tvas morritorecl by'a liquicl nitrogen-cople-cl Gc-cletector model (EO-Bl7L, Nolth Coast Scientific Clo). The absorbalce of t5e reference solution (Bengal pink in ethanol solr,rtion O lO.) : 0.6g) and the sarnple solution

, Gencral procadurc.t'or in uitt.o c-rperimcnts 2.-1. I. Ct'll cultttre t'onditiorts For irl r'i|r'o expcritl]ents, HUVEC, poolecl lionr several clonols

, Thesc cclls uL're I'c-lLrtinelv grr)\\,n in enclothclinl gr-p1',th nrcclit'r lil (EGM-2)' containing 2')i, letal borine serum (FBS), grorvtl.r factors ancl supplernents, alcl maintained according to thc manufacturer's instructions

, EMT-6) cells were grorvn in /) cm-plastlc ttssue culture flasks in RPMI 1640 medium supplemented with g%, heat inactivated fetal calf seruni, penicillin (100 i.u. mL t), streptomycin ( 100 pg mL-r) in an attnosphele of 37 "C and 5ol, Co2 atrnosphere. Cell culture inateiials were pur-chasecl from Costar (Dutscher', Bt'urnath, France) Cells were subcultuled by dispersal with 0.2591, trypsin and seeded 5x l0acells mL-1, Murine mamrnary calcinoma

Q. Fallavier-'france, TPP and the peptidic photoiensitizors \\,ere dissoh,ed in DMSO at a concentration of r mM

. Expression-oj-u, totnetry arrulvsis The expression of c"pj integrins was assessed by flow cytolnetry. Briefly, after trypsinization, 106 cells (HUVEC or EMT-6) were incubatea with a monoclonal anti-a'Br integrin antibody coupled to phycoerythrin (LM609, Chemicon International, Temecula' USA) duting I h at 4 "C, according to the manufacturer's recommendations

, Isotype-identical antibodies served as controls

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, Number of words in discussion, p.1326

, Non-standard abbreviations: Ahx, 6-aminohexanoic acid; a.i., arbitrary intensity; a.u., arbitrary units; DiOCo, 3,3'-dihexyloxacarbocyanine iodide; DLI, drug-light interval

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