`Declaration of liar! |.. White. 1711.1").
`
`IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
`
`Applicant:
`
`Fotini Sampalis
`
`Confirmation No.:
`
`3094
`
`Application No.:
`
`10/485,094
`
`Art Unit:
`
`1614
`
`Filed:
`
`Title:
`
`July 13, 2004
`
`Examiner:
`
`Gregg Polzmsky
`
`NATURAL MARINE SOURCE PI-IOSPIIOLIPIDS COMPRISING
`
`FLAVONOIDS, POLYUNSATURATED FATTY ACIDS AND
`THEIR APPLICATIONS
`
`Mail Stop Declaration
`Commissioner for Patents
`P.O. Box 1450
`
`Alexandria, VA 22313-l 450
`
`TION OF EARL L. WI*IITE PI*I.D. UNDER 37 C.F.R.
`
`1, Earl L. White, declare as follows:
`
`1.
`
`2.
`
`lam a US. citizen.
`
`I am presently President and CEO of MDX BioAnalytical Laboratory, Inc. in College
`
`Station TX, which offers, among other things, expert analytical services for identification of
`
`biosubstances.
`
`I have a Ph.D. in analytical chemistry and mass spectrometry from University of North
`
`W J
`
`.
`
`Carolina at Chapel Hill. Since 1985 I have worked professionally in the area of analytical
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`chemistry and mass spectrometry (26 years). I have served as Adjunct Professor of Chemistry,
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`Wake Forest University, Dept. of Chemistry and have published 27 peer reviewed journal
`
`articles.
`
`I presently serve as a Peer Reviewer for J. Chromatographic. Science and .1
`
`Chromatography.
`
`I am a member of the American Chemical Society (CNCS-Section Chairman
`
`'93, Chair-Elect/Program Chair '92, Secretary '91 and Treasurer '90), Mississippi Academy of
`
`Science, Society of Analytical Chemists of Pittsburgh, Applied Spectroscopy Society, Phi
`
`Lambda Upsilon Honorary Chemical Society, America Society for Mass Spectrometry, National
`
`Technical Association and Alpha Phi Alpha Fraternity, [ne., Triangie Area Mass Spectrometry
`
`AKBM 1099
`
`1
`
`NEP877ITC-00003351
`
`AKBM 1099
`
`
`
`Attorney Docket No. l"~ll7.PN—UUl/l)2l.lS 3l3663—2(}l3
`l)LICltll'illl()l1 of Tiarl l.. White. PILD.
`
`Discussion Group, National Organization of Black Chemists and Chemical Engineers
`
`(NOBChCE), Bay Area Mass Spectrometry Discussion group (BAMS) and the SF Bay Area
`
`Proteome Society. My CV is attached and labeled as Attachment A.
`
`4.
`
`1 am considered an expert in the area of identification of biomolecules using analytical
`
`techiques in general, and mass spectrometry, specifically.
`
`5.
`
`MD): BioAnalytical Laboratory, Inc. was contracted by Neptune Technologies and
`
`Bioressources of Quebec, Canada to analyze certain phospholipid samples (the "Beaudoin Oil
`
`Fractions”) and report which fatty acid phospholipids are present in the Beaudoin Oil Fractions.
`
`F"I'tl1ert1.1.o.re, [was asked to opirie on wl_1cthercei'tain fatty acid phospholipids were present or
`
`absent in the Beaudoin Oil Fractions. The result of this analysis follows.
`
`6.
`
`I received three Sample Sets from Neptune Technologies and Bioressources. each of the
`
`first two Sample Sets containing three separate Fractions labeled Beaudoin Oil Fractions 1. II and
`
`III, and the third Sample Set containing two separate Fractions labeled Beaudoin Oil Fractions I
`
`and II', for liquid chromotography/mass spectrometry (“LC/MS”) and liquid chromotography-
`
`mass spectrometry/ mass spectrometry (“LC-MS/MS") analysis. LCIMS is an widely accepted
`
`separation and identification technique used in the pharmaceutical industry to characterize
`
`organic molecules.
`
`I was to analyze the eight Fractions in the three Sample Sets and identify the
`
`fatty acids attached to the phospholipids (PL) present in each of the Fractions in each Sample
`
`Set. The PLs of interest include phosphatidylcholine (PC). phosphophatidyl—ethanolamine (PE)
`
`and phosphatidylinositol (Pl).
`
`METHODS
`
`7.
`
`All Fractions received were analyzed by LC/MS. Each Fraction was dissolved in
`
`chloroform and diluted to a concentration of 500 ng/pL in 20% Me0H in 0.1% formic acid (FA)
`
`and subjected to LC/MS. A l or 2 pL aliquot of each sample was injected onto a C18 column,
`
`separated on a Waters MicroMass CapLC and detected with a Waters MicroMass Q—TOF Micro
`
`quadrupole time—of—flight mass spectrometer with nano-electrospray ionization (ESI). The
`
`instrument was operated in the full scan or MS/MS positive ion mode for these Fractions.
`
`1 When the third run was performed for the third Sample Set there was not enough material remaining alter the ethyl
`acetate l‘TltCLlt)ll for analysis.
`
`-2-
`
`N EP877|TC-00003352
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`2
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`
`
`Attorney Docket No. NEI-‘N-001/02llS 313663-2013
`Declaration of Earl L. White. Pli.D.
`
`Continuum mass spectra were acquired over the mass range of 400-2000 amu with a scan time of
`
`1.80 s and an inter-scan delay of 0.1 s. The capillary, sample cone and extraction cone voltage
`
`were 3672, 30 and 2.5 V, respectively. The source temperature was held at 120°C, the cone N2
`
`gas flow was 50 L/h and the collision energy was held constant at 10 V. The HPLC column was
`
`a CVC Micro~Tech Cl 8WS-I 50EU nano column. HPLC/MS procedure; mobile phase A (0. l %
`
`FA HgOIACN, 955%) was held at 20% B (ACN: 0.1% FA in H20, 955%) for 4 min. and then
`
`programmed to 70% B at 5 min., 80% at 15 min. then to 100% B at 30 min. and held for 36 min.
`
`The flow rate was 7 uL/min. with a split ratio of about 6:1 yielding a flow through the column of
`
`approximately 600 nL/min. For MS/MS analysis, the Q-TOF was operated in the survey scan
`
`mode where data dependent MS/MS analysis was performed on all ions detected above a pre-
`
`determined intensity threshold. Optimum collision energies for compound dissociation were
`
`determined. Each Fraction was analyzed in duplicate for MS scan and at least once in the
`
`MS/MS mode.
`
`8.
`
`My full report is attached to this Declaration as Attachment B.
`
`RESULTS
`
`9.
`
`A list of fatty acid phospholipids detected in the Beaudoin Oi] Fractions is given in the
`
`Tables 1 and 2 (see Attachment B) with relative percentages based on area under the curve with
`
`the caveat that all PLs do not necessarily respond the same. These values should therefore be
`
`considered a semi-quantitative representation of the various PLs.
`
`10.
`
`Table 1 presents the results of Fractions I, II and II] for each Sample set. Table 2
`
`presents the same results grouped by Sample Sets 1, 2, and 3 for each Fraction therein.
`
`ll.
`PLs detected in the Fractions were primarily phosphatidylcholines as confirmed by the
`characteristic m/z 184 ion in the MS/MS spectra. With the exception of PL with molecular
`
`weight (MW) of 732.5 Da, PLs in an amount of;-_ 5% were low MW PLs. Six of the PLS
`
`detected in the samples (m/z 542, 568, 666, 808, 826 and 852) have molecular weights, which,
`
`without further analysis, could be considered evidence of a PC containing DHA and EPA, or a
`
`combination of DHA and EPA, however MS/MS spectra shown in the figures below confirm
`
`that these PLs do not have attached to the sn-1 and sn-2 positions of the glycerol backbone DHA.
`
`and DHA, EPA and EPA, DHA and EPA, or EPA. and DHA.
`-3.
`
`NEP877ITC-00003353
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`3
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`
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`Attorney Docket No. N1-LPN -00]/OZUS 313663-2013
`Declaration of Earl L. White. Pl1.D.
`
`12.
`
`Figures 1 — 3 show representative total ion ehromatograms for S00 ng/uL of each oil
`
`sample dissolved in CHCI3. Peak areas were calculated from the protonated molecular ions for
`
`each of the major peaks in the spectra. MS/MS spectra for a representative Beaudoin Oil
`
`Fraction sample are shown in Figures 4-9, and 11. Figure 10 is a representative MS!MS
`
`1“~:"F.:3fi‘436E‘/EJEEIE: %tTz?3”c{i‘.fio“n‘."s”""Z 5343 and
`Spectrum for 3 PC with 3 m“"“"'"" /‘x“tt‘;)r.“1‘t-,‘.4“t5?.t‘-’:€lt"1~fo.
`5423 are indicative of 302
`l_)eclzIrnt10I1oI' Earl I.. \Vl1tlc, PI1.D.ldicative Ofthe
`
`loss of a C20:5 (EPA) and C18:0 fatty acids from the protonated molecular ions. However, there
`
`was no ion observed at W2 of 499 which would have been indicative of a loss of 327 which is
`
`DHA from the protonated molecular ion at m/z of 826, which is indicative that there is no DHA
`
`attached to the phospholipid.
`
`13.
`
`It is my opinion that the Beaudoin Oil Fractions received and tested by me do not contain
`
`PLs which have attached to them DHA and DHA, EPA and EPA, DHA and EPA, or EPA and
`
`DHA, at the detection levels described above in paragraph 7 or represented in the spectra of
`
`Figures I~1l.
`
`[rest of page intcntiomtlly tell hlanlr]
`
`N EP877ITC-00003354
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`4
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`
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`Attorney Docket No. NEPN-001/O2US 313663-2013
`Declaration of Earl L. White, Ph.D.
`
`14.
`
`I further declare that all statetnents made herein of my own knowledge are true, and that
`
`all statements made on information and belief are believed to be true, and further, that those
`
`statements were made with the knowledge that Willfill false statements and the like so made are
`
`punishable by fine or imprisomncnt, or both, under Section 100] of Title 18 of the United States
`
`Code, and that such willful false statements may jeopardize the validity of the application or any
`
`patent issuing thereon.
`
`
`
`Earl L. White, Ph.D.
`
`Dated: May 3lJ_2_Q_l_l
`
`77227 VIIBN
`
`N EP877ITC-00003355
`
`5
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`
`
`£=“e.’I'Ti"‘-.C,"HMEI‘JT A
`
`EARL L. WHITE ~ Ciarricuium Vitae
`
`M 53,1; £§ia.At*.aE},»1ical {..aborai.(,~ry. Inc.
`PD. 80>: '.-7_’..'*,c'~':
`
`Wcllborn. TX 77881
`
`0i‘!'1c:.*: (979; 314-7368
`295
`
`
`
`E-dmzatima:
`
`University ofbianlz Caa‘C:i1'r‘:a
`at C‘h.apt:} Hill
`Chapel Hifi, Norfih Cur‘(71i:1z1,
`M aim:
`(.‘hen1isLry { /-\.nai \_/Licai)
`Gl‘i2dL1.’.’l9.CdI
`11111;: 1987
`
`Universityc»fPi11sburgh
`Piiisbtzrglz, Pcrm5;~/lwxrziz-;
`Major: {I‘i1emistr_y { Anaiyticai}
`
`Degree: M.S.
`
`Jackson Stats: University
`.Fe1I.‘kS0ra. Ikriissisfiippi
`Major: Chr:mi5lr;: {{)rgEmic—Ar:aEy1ica!)
`G1-aduatcd: Ailgllst 19'/fr
`Univcrsity of ?viissi,-ssippi Ixzflcdicai
`Ccr:to.;'. J2'!C'!vL7~.‘-{_1rI,,
`;"s’Ii*;:sis5@1'[J;.2i
`
`Dcgrcc-.: §’h.D.
`
`5933-1987
`
`M 2.55; Spa-ctmmetry
`
`E975-1977
`
`1975
`
`§973~i‘_3V7-4 (p-.a1'I.»z,§nac}
`
`Undergraduate Schooiz
`Ja.cksor=. State Coilegc
`.Facks<:m, I\/!is:si,:~.us:'ppé
`Majar:
`(I‘hemis1ry
`Cimduztécdz Dc'ccmbs3:' E9"/I
`
`imlfessimaaai Experienct-.:
`
`Degree: B.S.
`
`i96'7—i9’.7!
`
`.\1I‘Jrx iiioAnai31ic9.§ L:1lmratm'v, Inc.
`3 I/£}8—prcscn: President & CEO
`Eslzxblishcd MD; £12 2008 and incorporaml in 2009, nlanagc business: component and
`diraicizs 1cchau'c;21i £‘1mc;1i.c.ms. Marmga'::s lmdgcfi. pruzparcs quoiczzs, p:‘opu5a35.
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`fliigaratcd Bimnulccuic C'.m'_rg0:'ntiun, Tucsu . AZ 85755
`0'7;'O7~V 1 1/08
`Vice Presidentq Anaiyfical & Pharmaceutical Sciences
`1‘./l:«:;1a,t_zL: A<,lv.:mcc Amiylaczsi .::nd Qlmlgty (_.'c;-mroi
`luru.:i101zs 21%. the mr'pora1c igwc-1..
`,<;en1'm' mzmagemcni with ihe sLa[":'“ eaiisxwaies and budgetary :'equi:'e1m:n.t3.
`
`/£55251
`
`NEP877ITC-00003356
`
`6
`
`
`
`EARL L. ‘WHITE?
`{CV Ciriitkl)
`
`Larac Scaie Rink; 1-‘Cormration Vacawille (T/£95688
`
`
`
`09/02-
`
`{}4/E3/2s'.}C='7 Vice President. Advanncisd Aimiyticani Sciences & Direcmr, Quafiity
`Cmitrufi
`
`iht: {}0Fp(J!‘2}.iC law] 10
`furicliorzzs at,
`Mzgzizigc Advance Anaiyt.i¢‘,'al zmzl Quaiiiy (‘<.,mLmI
`include QC operations in (I3vvensbo1'o,
`559:" and Germazitown, MD.
`/Xssisa-I senior
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`
`Directtir, Atlvarzate Anaiyiicai Ream-urizais & Quality Cmitmi
`i£}«’99—G9/O2
`Eéistablished and ciirecied the Advanceci x-Xnaiyiical R.e5ouL'ce.~'.
`iL)1'vision iriciuding Assay
`DCVCiO1'P!‘:'1CI!§ Group. Dirccicd Quaiity C0ma'c.~i Group fur produciimi of ;'1h:1a'mz1c4:utic::1l
`prcacluma under CGMP guidcli-hes (proteins 4.:xp1‘csscd in _2‘v"ic:ofi4zna ijcm/zamiuna plzmis)
`including Phase i Ciiiiiflfii
`trims of 3 mari—}-§o‘R!gi<ir:'s
`lyn2p}mnm vaccin-3. Rclciiscd
`vaccines in Qu:12i=;_y Assmaizce for patients use and mziémaineci szabiiity sizadies. Directed
`pzmconzics uiiciions wiihin the Adwmcc Azialyiical Ros-;0‘-.11'cc.~; Division.
`
`Larva Scale Bioloav (.".m- uratiim rormeriv iiiusmlrce ‘l'echnolu -'iB.‘i
`
`Inc. . Vacaviile C.‘-‘K
`
`i(3.’98—i()."9€‘#
`
`Sr. Sciezitist
`
`(Zimiip which included siaffiizg with
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`approxiinatcziy ii’) scicntisi and piarchasing :55‘ mass spcciron1ctz'ic cquipiiicnz to include
`CiC'/'i\/ES, MALDLTOF, LC‘/Q—TOF S/MS and LCQ—MS/MS,
`
`RJ. R(‘\’{lt't§{l5 Tsrhaccu Cum am: Wiusta-n-Saican. NC
`
`Staff R&D Ciwniist. .Vl ass Spectrrrmetry {Swap Leader
`2,’88-0‘),:"‘}8
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`group, project niaiuzgczncna, budge: p:'c:_a7«:>:~a!, capital rsquigiiiiczit purchase, .'?.«llp(2l"s"iS-I.i.’,\I'; of
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`
`if!/%i5—i2/88
`
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`
`I{esgnc;~risibiEiL%es inciudeezg anaiyticai metimds developtiienl arid analyses, operaiicm. fltlti
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`
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`NEP877|TC-00003357
`
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`Senior Research Associate
`
`rc5can:§'1 on cnvironmcntai c§1r_~.a11§ca¥.~;
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`Alsm pubiishcd i.h(.‘.' first pccr-rcvicwcd1nanu5crip1 for CIIT.
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`in smali animai studies.
`
`'We:..-«fin!
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`
`
`l'N_!l§$£? R&D Pitts? in“ la PA
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`
`S11:r1n':c-i‘-E977 Aiaaiyzicai Chemist
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`
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`Uliiwrsity nf Pi?1sbur<,gl1. Pittsbiirgh, PA
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`Sr. Obs‘;c;‘w:r/Trains)‘, 91 “" ‘£)ivis3'c-11* 1""‘Bde, CSS—Task Force, Camp Pa1‘1«;s._ DLz'ni‘§n. CA
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`Femicipanz/’E)cn10ns:ira1orr Local c.1cn2m1:.ar_y, middicr high schanls and COH~'.’.g€3S.
`
`(iertificaécs and Awards:
`
`Ir1L<:rp:'c:t21I.ic»:1 01"ini'1*.11‘<:.d Sgmctm. Mississippi Section of The ;5m.1C1‘iC££fl C‘hc11‘;ical Scaciczy,
`AC5 Film Short C:.>ui.'sc. Jismuary 22.1971.
`
`in Gas CԤ11'on2ai0gr'z1phy,
`§'{c.Lcnti0r1
`EducaLic»21. Oczobcr I6, 1973.
`
`‘»‘v'z1si1ingt0n Liniv'c1'sity Scimoi of Continuing
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`COO.
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`
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`I000-IOIIIII
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`WI’/‘-\ Me:'im1'im1s Service .5-Xward, 1982.
`Elected V ‘ho’-a—\.Vho in l,l1~L’. Sc-um and so=.nhwc,s1 an 1933.
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`Recigaieui ol‘i}1e
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`§"eEimv'sE':ip, E984-B5
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`Gas C‘hron1aiagraphy Tn_mb1u.shoo!;ing c<_n.:rsc._ HewicLL—Paukaa‘d. Atlanta, GA, Septcnzbcr 27'
`1987.
`
`introduction to CA LS i.'."o1,arsc,
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`RJ. 1'{cyr1olds
`
`‘iohacco Company, W’inston-Saicm, NC‘,
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`Fobr1:.2:ry E4. 1986.
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`[UR 1‘vianagc1ncn1 Dcveir;-pn1<:a11 Prczgazn C OU.I‘S£.’.., RJ. Reyrzoids Tobarcccz Comparry.
`Winsaon—Sa.1cn1, NC. June 27" 3988.
`
`'70_'~; and '7f.}SE Basic Opc1'a1im1., S:;1vans1a}*., GA. O-ciobcr, F988.
`VG Instruuicraifs,
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`‘w'ho's~Wh£,1 in Scicracn: and Ezxginocr in 5992
`National Ufloan Lr;a_guc"'s Black Ex42C‘;1?.iVCS Exci‘1ang_c: Prog_;;i'a1*.1 {BEEP} 5 Yoga‘ Service
`Award. 1995.
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`RJR Pm_§r:c1 l..e:1de.r "{'rai.nir-.3. Pmgr:z1:n_, IE-‘e‘m'ua:y, 3992.
`Ccnirai Norila Caroiina Sccfion, ACS Pa'r;sidc1';9.”s Awmd, 1994‘
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`0, Robert £)iMa:'c0 R&D '§'eam ./\ward (‘or Resuits Thmug}: I)ive;'si'i_y E?}:ciii1aiio11, W95.
`C‘cmra'i North Cartnliaaa Scc:ic»a1, AC8‘ C)=.1LsLanding Service Award, 1995.
`Mediation Saarvices’ o!'}9‘0:'sy:h £f'0m11y. §’asL-(L‘E':aér /a=.»u'3.;‘d. 1998
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`Winsiora-Salem Stare Univor3i1y,~"RJ R. Partners Pmgran1 i’\4ca1toa'—c-i'-I.11<:—ycar Award. J993.
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`E-Sew]-:1:-Packard Gas (?}1:‘o:‘z1atog;rz1ph_y Tlrryubieszhootirag course. Atlanta, 113A, 1974.
`
`Liquid C!'11‘1)n1u§.0gr2'zphy WcJrkshup._ Waters Ass-*_:r.7iazcs. 1‘vfl§1i'o=;d. MA. 3975.
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`Mississippi ./-Xcacierny ofscience (I‘nnven11'm:, Jae!-.;5«:or, fx/IS, 1975
`
`Mass Spzjctral h‘l1Cl‘[J-?‘L3l.Ei1.iC-11 C<:.-ursc (Frcfi McLz,-,1"fcr1y)., Raleigh, NC, 1978,
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`N0:"&}1 (famlina .l'\cadcn1yoi'fS§ci.«snce, Grcen5~,bom. NC‘, 1979.
`Anwrican Sr_n:§cLy for M2255 S;3cc1ro11ac1ry, Minneapolis, MN, Honoéulu. H}, San A:1Lc»a1ic»,
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`
`1988.
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